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Key West Holiday Vacation with Pools

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    Travellers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    331 Matching Rentals in Key WestView all 430 rentals
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (39)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key West Beachfront Luxury 2/2 Condo  A2121 / 39
    (38)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (34)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (28)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    Great place to relax. Clean. Plenty of room. Great pool. Close to where you want to be. I'll be back.
    Reviewed 14 February 2017
    Rented this place for my sister's bachelorette party and we had an amazing stay. It really is walking distance to everything and the shared pool was great. It was such a bonus...
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2017
    As advertised, this apartment is truly in the perfect location. A mere block away from Duval St. and easy walking distance from most attractions, museums, galleries, stores...
    Reviewed 27 March 2017
    We really enjoyed our time at the Bahama House. The condo was great but our favorite thing was the pool area. Very nice!! Also, we had a problem with the cable and it was taken...
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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. 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 endless party, The Nassau...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anchor Drop Key West A3071 / 51
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for...
    Reviewed 13 June 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    About this property
    Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless Internet. This is your home...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful Townhome at the entrance to Key West1 / 16
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Ocean Views
    • Wi-Fi
    • Parking
    • Washer
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2016
    This location is in Stock Island close to airport, beaches and all the attractions. Exceptionally clean accommodations and was very safe. The pool at the unit was breathtaking...
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    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Sunrise at Seaside Condo 2 Bedroom1 / 12
    (17)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2017
    The place was very nice and clean. There were plenty of blankets, pillows, towels, etc. The breeze was fantastic. The balcony was secluded enough that I didn't feel like people...
    Reviewed 25 October 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Key West Condo close to the Ocean1 / 22
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
    Reviewed 22 November 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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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.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Key West Florida Beachfront Condo1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedroom Oceanfront Condo Key West1 / 14
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shelleys Rooftop Hideaway1 / 15
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    KWO - 2 BR/2 Bath, Private Pool, Separate Cottage1 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    We had an amazing time in Key West and we were pleased with the rental. We would go back to Key West Oasis for our next visit.
    Reviewed 17 March 2017
    Our vacation at Key West Oasis was definitely one of the best trips we’ve ever been on. From start to finish it was the perfect trip. I spoke with Kim when I booked the trip...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    LA DOLCE VITA, OLD TOWN!!  STEPS TO DUVAL!! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!1 / 27
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Porch
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2016
    If your looking for a conveniently located place to stay, in a quiet neighborhood ,this is the place. We chose this rental based on the interior, facilities, location and...
    Reviewed 4 October 2016
    The art deco was well done through the studio apartment. You are literally 50 feet from Duval St and make 500 yards to southern most point. The area is quite and well kept but...
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    About this property
    La Dolce Vita is just steps to Duval Street! "La Dolce Vita" is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room for a...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Sauna
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comforts of home away from home....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Sauna
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean. This unit has a remodeled Kitchen and bathrooms also. Guest pays $200 cleaning fee in addition to the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West condo! Bring your own boat!1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Washer
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 25 October 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    About this property
    Come down and take part in in Key West's many fishing tournaments! 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 friendly condo in...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 14
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The condo was very nice and centrally located. They had everything we needed. Located very close to the airport, but the noise was never an issue. My favorite part was the...
    Reviewed 28 March 2017
    This condo has: comfortable beds, a very functional kitchen with newer appliances, good bathrooms with good water pressure in the showers, a covered reserved parking space,(kept...
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    HISTORIC KEY WEST  - Main House - SLEEPS 10 - Weekly Rates for Monthly Stays1 / 23
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Grill
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
    Reviewed 28 November 2011
    I rented The Main House at Bahama Gardens for a family vacation of about 10 days over Thanksgiving. There were 5 of us, myself, my husband, two adult sons and one son's...
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    About this property
    OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of ten (10) guests - (1) queen bed, (1) full bed, (1)...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    HYATT SUNSET HARBOR 200 SUNSET LANE KEY WEST. 1 week rental 5/28 - 6/04 only1 / 9
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Two couples sharing 2 bd 2 3/4 ba two floor unit 512. Arrived just at check in time. Concierge took time to give us coupons and tell us where things were on a map. After we...
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    About this property
    Hyatt Sunset Harbour Residence Club. *2016 Certificate of Excellence Winner TripAdvisor* **1 WEEK RENTAL 5/28/17 to 6/04/17**. Location, Location, Location. Private Balcony. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. Can accommodate up to six people . TV's...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Summer Blow Out! $300 off. Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    We had such an awesome time in Key West, and it all started with our accommodations at Tiki Beach Too! The Shipyard complex where the condo is located is in the perfect place...
    Reviewed 14 July 2016
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 14
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 14 July 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bimini Key West Penthouse C4241 / 34
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 2 January 2012
    We had an enjoyable experience from the time we arrived at 1800 Atlantic until we left. The nice security guard on duty on Sunday night couldn't have been more helpful. The...
    Reviewed 15 July 2010
    Every facet of our stay was perfect. We have stayed in many other places in Key West, and this is by far our favorite! We have stayed in this particular unit several times, and...
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    Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility 2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared, previously owned by the VP of Sony his taste was impeccable. The Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    This wonderful property has brand new living and bedroom furniture in 2016, King bed in the master bedroom, 2 twins in the 2nd bedroom and a memory foam luxury queen sleeper in the living room will comfortably accommodate your party. Watch the sunrise from your private balcony. Enjoy the balmy...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Atlantic Paradise Found C2321 / 40
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Reviewed 9 September 2010
    The condo we stayed in had obviously been remodeled. It was gorgeous with plenty of space for 4 people! Also, the pool and jacuzzi were huge! We really enjoyed the accomodations...
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    About this property
    1800 Atlantic Condominiums Unit C232 2 Bedroom. Ocean View. Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    HISTORIC KEY WEST - Turtle House - Sleeps 6 - Weekly Rates for Monthly Stays1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 4 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    Beginning June 1st until October 1st, the cost to stay in the Turtle House for any period of time from 1-30 nights, is $5,500. The nightly rate posted on on this site assumes a thirty night rental term, in accordance with the Key West Rental Ordinance. OVERVIEW The Turtle House is a 100+ year...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1800 Atlantic Condominiums Unit C439 Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, two bath penthouse condo has just been upgraded including a large, well equipped, open-design kitchen with all new appliances, bamboo cabinets, granite counter tops and an elegant...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Truman Annex Irish Condo Innisfree1 / 33
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 24 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    About this property
    Enjoy this lovely two bedroom two bath garden and pool view unit at 1800 Atlantic, You even get a peep of the ocean from your 40ft private balcony. Located at the Premier 1800 Atlantic complex on the Atlantic ocean at the end of Smathers Beach. This unit has all you need to enjoy and relax with all...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
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    • Shared Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
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    Pet friendly
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    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunrise off Southard- Newly Remodeled in May  See our August Discounts!1 / 17
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    About this property
    Location, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers tropical beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Flip Flop Retreat Key West- Downtown with a pool1 / 30
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 November 2016
    This was our second time renting a this wonderful Condo. Owner is always updating his condo and likes feedback from renters.Plenty of pans, glasses and dishes but only has 4...
    Reviewed 4 January 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
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    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    About this property
    Amazing sweeping views of the Atlantic from Mojito;s in Paradise. Watch the sun rise over the Atlantic from the comfort of your King size bed in both bedrooms, access to the private balcony from both bedrooms and living room. Full kitchen. Just a stones throw from the beautiful pool and Jacuzzi....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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