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Condos in Key West, FL

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    All 590 Rentals in Key West
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Welcome, see what other travellers are looking for in Key West
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    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • There Are Tennis...
    • Internet Access
    • Hot Tub
    • Washer
    • DVD Player
    • Satellite TV
    • Watersports Nearby
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    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 28 May 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed 30 March 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    1 / 26
    5 of 5 stars (30) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Sauna
    • Satellite TV
    • Waterfront
    • Watersports Nearby
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 7 April 2015
    Our family enjoyed this well stocked condo. They provided bikes to ride to the beach along with beach towels, beach chairs, umbrella, and cooler. The covered secure parking was...
    5 of 5 stars Reviewed 25 March 2015
    The condo is very spacious, lots of room for everyone and in a great location. The owners left us some very helpful tips and ideas for what to do in Key West. The Condo was clean...
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    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Parking
    • Hairdryer
    • TV
    • DVD Player
    • Private Outdoor...
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after... View all property information
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    Key West, Florida Keys 33040
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    $2,136
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    1 / 26
    5 of 5 stars (24) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Washer
    • Internet Access
    • Satellite TV
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 16 June 2015
    Spotlessly clean place. Everything as advertised. Quiet neighborhood in a semi-gated community. We took the auto-train to Sanford and drove down to Key West. Many quality...
    5 of 5 stars Reviewed 5 May 2015
    We scheduled our vacation with Jim and Joanne at Casa Del Sol and experienced a no hassle application. Our friendly hosts gave us all the information we needed to enjoy ourselves...
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    1 / 16
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Watersports Nearby
    • Grill
    • Air Conditioning
    • Refrigerator
    • Washer
    • TV
    • Wi-Fi
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 June 2015
    The pool was very small but offered cooling refreshment still. Old house, but satisfied our needs. Not overly stocked in the kitchen, but good frig. and close to grocery store.
    5 of 5 stars Reviewed 28 May 2015
    Great place very handy location, close to Duval St plus a great deli grocery store with good prices. Some parking in very crowded Key West which is a bonus. Place is really nice...
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    $157
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    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Shared Garden
    • Parking
    • Towels Provided
    • Linens Provided
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Live in luxury poolside in a beautifully furnished studio (private room and full bath) apartment, situated in a quiet, coveted residential Key West neighborhood. Walk right outside your door into an enchanting, very nicely landscaped pool/deck area for your enjoyment. You'll be strategically... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $371
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    1 / 26
    5 of 5 stars (16) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Water Views
    • Wi-Fi
    • TV
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ************************************************************************************************* TAKE 20%+ OFF: -- Stay July 20 - 23 (3 nights) and pay a reduced rate of $800 for all three nights instead of $1,020. -- Note, taxes and fees will be added to all rates.... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 23 June 2015
    My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view...
    5 of 5 stars Reviewed 16 June 2015
    My husband and I stayed at this condo for 2 weeks. Had the best vacation ever. The view from the balcony is fabulous and tranquil. Didn't want to leave. The condo itself is...
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Deck
    • Water Views
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 May 2014
    The condo was exactly what I was looking for and it was represented accurately. It was about fifteen minutes from Duval street, had a water view, it was quiet and the interior...
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    $325
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    1 / 14
    4.5 of 5 stars (15) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Refrigerator
    • Wi-Fi
    • Dryer
    • Grill
    • TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 21 June 2015
    The Grand Bahama suite was spotless clean, beautifully decorated , perfectly located to walk everywhere. The kitchen had all the essentials and the washer dryer made it very...
    3 of 5 stars Reviewed 17 June 2015
    We arrived at approximately 3:30 p.m. we found the apartment or unit and gained entry easily. The unit was exactly like the pictures and what we expected. It is approximately a...
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    $232
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    1 / 5
    3.5 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Shared Tennis Court
    • Grill
    • Air Conditioning
    • Internet Access
    • Garage
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 25 May 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
    3 of 5 stars Reviewed 3 September 2013
    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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    $1,884
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    1 / 4
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Hot Tub
    • Water Views
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
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    $546
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    1 / 32
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Linens Provided
    • Parking
    • Hot Tub
    • Balcony
    • Ocean Views
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $295
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    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Waterfront
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    You have the use of one of four private cabins each with its own marine style bathroom and queen like bed for $235.. Three cabins available for six or less guest for $695. Captain Charles and wife Deborah use one cabin. You may choose our sunset sail for $50 per person that includes snacks and non... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $320
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    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Washer
    • Elevator/Lift access
    • Watersports Nearby
    • There Are Tennis...
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,884
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    1 / 6
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Cooker
    • Internet Access
    • Balcony
    • Linens Provided
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $230
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • Watersports Nearby
    • Elevator/Lift access
    • Air Conditioning
    • Shared Tennis Court
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    $471
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Water Park Nearby
    • Waterfront
    • There Are Tennis...
    • Water Views
    • Ocean Views
    • Washer
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Look at this! July 4th weekend is open for your holiday stay! Obsession 37'ft. 1979 O'Day completely renovated with new interior and new varnish and paint throughout. $375/night for two people three nights preferred minimum. Half day 4 hour sail worth $600 included free (please plan cash 20% tip... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $438
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    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Water Views
    • DVD Player
    • Wi-Fi
    • TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 May 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
    5 of 5 stars Reviewed 25 May 2015
    It was a fun and unique vacation! At first it took some getting used to, flushing the toilets, water supply, close quarters, etc. But by the end that's what made it memorable. The...
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    $314
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    1 / 30
    4.5 of 5 stars (56) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (56) Make Enquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 March 2015
    We loved our vacation! The house was in a great location, easily accessible to many of the best rated restaurants and local convenient stores. We LOVED the provided bikes and rode...
    5 of 5 stars Reviewed 8 February 2015
    Nice condo and only ten minutes from downtown. Judy was great to work with. Pool on property was enjoyed by our family.
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    $264
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    1 / 27
    5 of 5 stars (41) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (41) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Stereo System
    • Wi-Fi
    • Satellite TV
    • Watersports Nearby
    • Air Conditioning
    • Staffed Property
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 June 2015
    It is away from the loud touristy area, which is what I wanted. We saved a ton of ,only by cooking our own meals. Condo was nice and clean. Beds were pretty comfortable. Pool...
    5 of 5 stars Reviewed 11 June 2015
    This property and Condo were awesome! I would highly recommend this unit and owner. The complex is conveniently located. Easy to find and well appointed. This is the best...
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    $4,397
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    1 / 54
    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Deck
    • Patio
    • Stereo System
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $8,731
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    1 / 18
    3 Bedrooms / 5 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Waterfront
    • Game Room
    • Hot Tub
    • Watersports Nearby
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
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    Key West, Florida Keys 33040
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    $314
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Water Views
    • Deck
    • Air Conditioning
    • Watersports Nearby
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 18 May 2015
    After a bit of a problem confirming the reservation, and no help from Trip Advisor, we arrived as scheduled on 5-15 and were met by Yanna who gave us a detailed tour of the boat...
    5 of 5 stars Reviewed 6 March 2015
    We spent 3 nights on this boat. James the owner was easy going and welcoming. He explained all we needed to know and was available by phone for any questions or concerns. Boat...
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Watersports Nearby
    • Waterfront
    • Shared Tennis Court
    • Housekeeping...
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 May 2015
    My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck...
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • TV
    • Refrigerator
    • Grill
    • Patio
    • Porch
    • Watersports Nearby
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
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    Key West, Florida Keys 33040
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    $13,505
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Housekeeping...
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    AVAILABLE FOR STAYS OF 28 DAYS OR LONGER. Vacation in style in this 2 bedroom, 2 bathroom beautifully furnished Keys Home, with lush landscaping with over 20 palm trees, tiki hut/bar with bar stools, heated swimming pool, pool deck chairs, private sandy beach, outdoor deck with dining, outdoor... View all property information
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    Key West, Florida Keys 33040
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    $2,513
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Private Outdoor...
    • Air Conditioning
    • Deck
    • Internet Access
    • Washer
    • Dryer
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    ******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a... View all property information
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    Key West, Florida Keys 33040
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    $2,261
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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    Key West, Florida Keys 33040
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    $258
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    5 of 5 stars (45) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Shared Tennis Court
    • Stereo System
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 11 June 2015
    Grandparents, Children,Grandchildren, we all had a great stay. Our experience ranged from charter boat fishing to trips to the beach.
    5 of 5 stars Reviewed 24 February 2015
    This trip to Key West was partially a college graduation present for our son and a family vacation. We had the most wonderful week and this was partially due to our stay at...
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    $230
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Washer
    • Air Conditioning
    • Dryer
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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    Key West, Florida Keys 33040
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    $5,653
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    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Wi-Fi
    • Refrigerator
    • Air Conditioning
    • Hot Tub
    • TV
    • Dryer
    • Cooker
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
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    $2,513
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Towels Provided
    • Secure Parking
    • Linens Provided
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Downtown Key West, one block from Southernmost Point, one block from Hemingway House, walking distance to all mojor tourist attractions, restaurants, galleries, beaches. Three bedroom, two bath totally renovated, on site parking, rear patio. Central Air, granite counters, stainless appliances.... View all property information
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    Key West, Florida Keys 33040
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    $5,025
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Towels Provided
    • Parking
    • Shared Garden
    • Linens Provided
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Two bedroom, two bath, totally renovated in 2015, all new, marble floors, 10 foot ceilings, granite counters, walking distance to all major tourist attractions, one site parking, one block from Southernmost Point, one block from famous Duval Street. local beach is less than one mile, restaurants,... View all property information
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    Key West, Florida Keys 33040
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    $247
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    1 / 11
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Elevator/Lift access
    • Gym
    • Private Tennis Court
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 June 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
    5 of 5 stars Reviewed 22 March 2014
    A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
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    $440
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    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Waterfront
    • Refrigerator
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Gym
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 18 May 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
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    1 / 27
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • DVD Player
    • TV
    • Internet Access
    • Air Conditioning
    • Terrace
    • Parking
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 January 2015
    We stayed at City Cay over the Thanksgiving holiday. The condo is on the second floor of a building in the Shipyard Annex of Truman's Annex complex. We had wanted to stay in...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Ocean Views
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Shared Tennis Court
    • Satellite TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
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    Key West, Florida Keys 33040
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    $2,795
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
    traveller have booked this property
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    Amenities & Details
    • Ocean Views
    • Shared Tennis Court
    • Pool Table
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
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    Key West, Florida Keys 33040
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    $565
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    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Stereo System
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 29 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    Amenities & Details
    • Shared Tennis Court
    • Gym
    • Internet Access
    • Air Conditioning
    • Dryer
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 25 March 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed 5 March 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
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    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • TV
    • Deck
    • Hot Tub
    • Sauna
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    We are situated in New Town on the paradise island of Key West, about 12 minutes drive from downtown Duval Street. This romantic studio cottage consists of a bedroom with very comfortable king sized bed and a bathroom, with a pool and lush landscaping right outside your door. It has air... View all property information
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    Key West, Florida Keys 33040
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    $1,759
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    5 of 5 stars (16) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Outdoor Dining Area
    • Grill
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 24 January 2015
    The Key West Garden House is amazing. It is walkable to any location in Old Town and serves as a nice respite for down time. Susan was incredibly helpful with places to eat and...
    5 of 5 stars Reviewed 23 November 2014
    This house is in the most perfect location to enjoy Key West. Right in the historic district, close enough to walk anywhere, yet on a quiet side street that felt miles away form...
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    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Water Views
    • Internet Access
    • Elevator/Lift access
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Shared Tennis Court
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 14 October 2014
    My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
    5 of 5 stars Reviewed 11 August 2014
    My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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    $363
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $377
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    1 / 22
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 8 April 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    $3,078
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    1 / 23
    1 Bedroom / 2 Bathrooms / Sleeps 2
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hairdryer
    • TV
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    ROBIN'S ROOST (monthly rental): In a quiet local neighborhood, open living space in this 1-bedroom, 2-story condo leads to your private backyard with jacuzzi. Kitchen with breakfast bar, living room with sleeper sofa, dining area, and half bath under the stairs. Bedroom is upstairs with full... View all property information
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    Location Information
    Key West, Florida Keys 33040
    Key West Vacation Rentals

    Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

    Where to rent in Key West, Florida

    Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

    Key West Bars and Restaurants

    Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

    Sightseeing and Activities in Key West

    Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.