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Condos in Key West, FL

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    $225
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    1 / 8
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    $122
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • ?
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    About this property
    Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family... View all property information
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    2 of 5 stars Reviewed 15 April 2014
    We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
    5 of 5 stars Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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    1 / 22
    4.5 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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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    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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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Private Indoor Pool
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Charming 2 bedroom 2 bath sleeps six Single Family Home. Located in a lovely casa marina neighborhood, this charming furnished 2 bedroom home features an open floor plan with cathedral ceilings, French doors that open to a spacious shared deck, two off-street parking spaces, washer/dryer, central... View all property information
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    1 / 20
    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    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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    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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    1 / 15
    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    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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    1 / 12
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Washer
    • Wi-Fi
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    • Suitable for children
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    About this property
    Reasonable, couples, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven. Washer/dryer enclosed on deck.... View all property information
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    1 / 21
    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    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...
    5 of 5 stars Reviewed 3 March 2015
    For sail boat minded people this is perfect : comfortable boat, beautiful yacht club and possibility to enjoy environment with kayaks. After visit of crowded key west it's very...
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    $329
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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    5 of 5 stars Reviewed 18 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed 2 March 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    1 / 10
    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    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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    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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    5 of 5 stars (6) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    5 of 5 stars Reviewed 24 April 2015
    12 old friends rented all 4 condos and had the absolute best time. The condos were great , clean ,bright, cherry and that pool OMG was too fabulous for words. Loved the market...
    5 of 5 stars Reviewed 28 January 2015
    Loved the house, pool, location. Beds were very comfortable. Loved everything about it. Already have friends asking about rental.
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    1 / 17
    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
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    5 of 5 stars Reviewed 10 April 2015
    Had a fantastic holiday in the Bimini Suite. It was clean, well decorated and probably had the most comfy bed I've ever slept in whilst away from home. The garden area was lovely...
    5 of 5 stars Reviewed 17 March 2015
    Stayed in the Bimini Suite with 2 friends . My wife made the reservations and dealt directly with Evelyn and David who were always reachable and friendly . You will not regret...
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    1 / 16
    4.5 of 5 stars (48) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (48) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
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    4 of 5 stars Reviewed 19 September 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
    5 of 5 stars Reviewed 11 May 2013
    My new husband and I selected ann Street Tranquility for our honeymoon and we could not have been more happy with our choice!Everything about ann Street Tranquility was amazing...
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    5 of 5 stars (17) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
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    • Internet Access
    • Shared Outdoor Pool...
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    Suitability
    • Pets allowed
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
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    5 of 5 stars Reviewed 5 April 2015
    Great old house with lots of character in the perfect location. Very clean, comfortable beds, and a great pool area. Had one minor issue that management fixed for us right away...
    5 of 5 stars Reviewed 2 February 2015
    We stayed here for a week, for our destination wedding. We were able to entertain all of our wedding guests from out of town. Perfect size for our needs; great front porch...
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    4 of 5 stars (5) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    1207 Heaven on Florida is Key West Casual at it's best! Decorated by a world travelling, gallery Curator/Artist/Entrepreneur- the place is a refreshing twist of elegant, sophisticated & funky with local & international art, contemporary & mid-century modern decor & comfort. The layout includes 2... View all property information
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    5 of 5 stars Reviewed 29 March 2015
    I brought 5 of my friends to Key West for a weekend of R&R and stayed at Barb's amazing house in old town. Barb was such a great host, making sure we had everything we needed and...
    5 of 5 stars Reviewed 26 March 2015
    My husband and I stayed here along with my sister and her husband in March 2015. We felt like we had our own private paradise hidden away in a quiet residential neighborhood only...
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    1 / 26
    5 of 5 stars (21) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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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    5 of 5 stars Reviewed 29 January 2015
    We stayed at casa del sol thanksgiving week, Nov 2014. What a great place to stay. Jim is awesome n pleasant to deal with. Having 2 teenagers, 18/16, they could walk...
    5 of 5 stars Reviewed 18 January 2015
    Recently spent one week at Casa del Sol. This rental was in a perfect location, wonderful amenities, tastefully decorated and as neat as a pin. The Truman Annex location was...
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    4.5 of 5 stars (56) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    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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    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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    1 / 25
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
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    1 / 25
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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    5 of 5 stars Reviewed 17 April 2014
    This house was gorgeous. Clean, updated and simply beautiful. It also had everything we needed...hair dryers, ironing board, laundry room, etc. If you are looking for something...
    5 of 5 stars Reviewed 9 October 2013
    Six women stayed in this beautiful townhome for three nights for a girls getaway. We would normally have booked hotel rooms, but staying here far exceeded our expectations and we...
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    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    About this property
    Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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    3 of 5 stars Reviewed 11 February 2015
    Clean, noisy window air conditioner, ants. Close to water. Staff pleasant and efficient. Musty smell but comfortable bed.
    4 of 5 stars Reviewed 9 July 2014
    Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
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    5 of 5 stars (37) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • 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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    5 of 5 stars Reviewed 17 April 2015
    This was our 3rd time staying at Pam's Condo and it felt like coming home. We LOVE this place! It is just the best having the kitchen. We caught fish on this trip and took them...
    5 of 5 stars Reviewed 7 April 2015
    This was my first time doing a condo rental through TripAdvisor and the experience was great from start to finish. We stayed 5 nights and found the condo to be exactly as...
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    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
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    • Grill
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    About this property
    The Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa which converts to a... View all property information
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    5 of 5 stars Reviewed 12 July 2014
    My friend and I stayed at the Bonaire Suite and it was perfect! Cute bungalow style with plenty of room and amenities. So close to Duval, but you couldn't hear the roar, which...
    5 of 5 stars Reviewed 12 June 2014
    Perfect location! Half block from Duval street. Very cozy and well equipped and lovely pool area. I highly recommend this place.
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    4.5 of 5 stars (41) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony on the 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit.... View all property information
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    3 of 5 stars Reviewed 21 May 2014
    In last year's review, I said I would unhesitatingly stay here again. I did. And was far less charmed. I do love the Truman Annex location and the design of the condo. The...
    5 of 5 stars Reviewed 18 June 2013
    very nice place in excellent location
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    5 of 5 stars (30) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    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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    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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    5 of 5 stars (44) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
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    • 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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    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...
    5 of 5 stars Reviewed 1 February 2015
    All four of us were very happy with our stay ... very clean, beautiful, safe, conveinient location. Inside of the condo is as pictured and we couldn't have been more pleased with...
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    4 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    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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    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...
    4 of 5 stars Reviewed 26 January 2015
    We were pleasantly surprised with the condo. 2 separate bedrooms with 2 separate bathrooms and a kitchen and Living room. Bar stools for the kitchen bar. The condo was fully...
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    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • ?
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    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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    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...
    5 of 5 stars Reviewed 23 January 2014
    The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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    5 of 5 stars (40) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    5 of 5 stars Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    5 of 5 stars Reviewed 31 May 2013
    Great central location. Walking distance to most things of interest. Liked the fact it's a Gated community with assigned parking place. Not beach front, but that wasn't important...
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    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • 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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    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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    4.5 of 5 stars (10) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
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    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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    5 of 5 stars Reviewed 5 February 2015
    Easy walking to Duval St., waterfront and many Key West attractions. Plenty of room for three couples. Pool area is great! Beds are comfortable. Good value.
    5 of 5 stars Reviewed 25 January 2015
    This place far exceeded our expectations and was quite cozy. We weren't aware of the pool until we arrived so seeing such a great perk just added to a wonderful experience.
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    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Hot Tub
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    • Ocean Views
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    About this property
    ************************************************************************************************* TAKE 25% OFF: -- Stay May 14-17(3 nights) and pay a reduced rate of $1,000 for all three nights instead of $1,5. -- Note, taxes and fees will be added to all rates.... View all property information
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    5 of 5 stars Reviewed 7 December 2014
    All the previous reviews are completely accurate. The location is quiet and peaceful but only minutes away (by car) from Duval Street. Inside, the condo is very well-appointed...
    5 of 5 stars Reviewed 2 November 2014
    This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
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    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
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    • Elder access
    About this property
    Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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    5 of 5 stars Reviewed 28 October 2014
    Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
    4 of 5 stars Reviewed 11 September 2014
    Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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    4.5 of 5 stars (49) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • x
    • x
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    • ?
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    About this property
    Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a... View all property information
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    4 of 5 stars Reviewed 21 November 2014
    My husband and I recently enjoyed a wonderful week long stay at this condo in Key West! We certainly made the right choice when selecting Colony Poolside for our vacation. This...
    5 of 5 stars Reviewed 30 August 2014
    Just a few minutes walk from duval, a perfect balance of having all the bars etc nearby, but peaceful enough when sitting out by the pool that you're not disturbed by noise...
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    5 of 5 stars (16) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    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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    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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    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    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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    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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    3.5 of 5 stars (10) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Mermaid Cove is a small island compound that is great for large groups or big families. It's made up of 2 apartments and 2 cottages with an intimate courtyard in the middle with BBQ grill and table, shaded by a massive mango tree. Located right on Duval Street, Mermaid is just a block and a half... View all property information
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    2 of 5 stars Reviewed 8 January 2015
    I stayed at this property last August (booked by someone else) and have to say that it was an experience. We rented the whole property for 5 adults and the overall consensus was...
    5 of 5 stars Reviewed 2 January 2015
    If you want to experience Key West like the locals do, then Mermaid Cove is for you. Quaint hideaway in the midst of historic Key West close to shops and few restaurants Mermaid...
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    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • Suitable for children
    • ?
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    • ?
    • ?
    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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    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Satellite TV
    • Sauna
    • Waterfront
    • Water Views
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    • Pets allowed
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    • Suitable for children
    • ?
    • ?
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    • ?
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    About this property
    Construido en la década de 1950, el complejo rezuma encanto de la época, sin retraso en el crecimiento de las comodidades. Las habitaciones cuentan con obras de arte cubano, TV de pantalla plana, mini-nevera, y hamacas. El hotel presta huéspedes coloridos sarongs para relajarse, y algunas... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Ocean Views
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • x
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    About this property
    For six or less adults only. The 'ANAA B' is 41ft long and 24ft wide Catamaran with 2 diesel engines and a powerful sloop rigged sail plan. You will enjoy our complimentary sunset sail. The interior is comfortable with four cabins each with a marine bathroom with toilet and shower. The beds are... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • Suitable for children
    • ?
    • x
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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • x
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    About this property
    This stunning 2 bedroom/2 bath suite can accommodate up to 6 guests. Whether you want the hustle and bustle of Key West or just want to kick back and relax, this resort has it all. View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    • ?
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    About this property
    Gorgeous one bedroom apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. One bedroom one bath floor plan maximizes the space in this airy tree top apartment.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Pets allowed
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    • Suitable for children
    • x
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    • ?
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • ?
    • x
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    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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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Sauna
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    • ?
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    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
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    • Gym
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    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
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    • x
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    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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    3.5 of 5 stars (3) Average
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly... View all property information
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    5 of 5 stars Reviewed 18 June 2009
    We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful...
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    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.