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House Rentals and Apartments in Key West, FL

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    All 546 Rentals in Key West
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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    1 / 12
    4.5 of 5 stars (60) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    1 / 21
    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    1 / 27
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 19, 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
    4 of 5 stars Reviewed January 15, 2014
    Love Key West and staying at the Shipyard condominiums put us right with in walking distance to every thing we love to do. We have been to Key West four times in four years and...
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Ocean Views
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    About this property
    AVAILABLE FOR STAYS OF 28 DAYS OR LONGER. Vacation in style in this 2 bedroom, 2 bathroom beautifully furnished Keys Home, with lush landscaping with over 20 palm trees, tiki hut/bar with bar stools, heated swimming pool, pool deck chairs, private sandy beach, outdoor deck with dining, outdoor... View all property information
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    Key West, Florida Keys 33040
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    1 / 20
    14 Bedrooms / 14 Bathrooms / Sleeps 28
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    About this property
    The Best Kept Secret in Key West. This family owned and operated Historic Victorian Inn is centrally in Key West's Historic District. A true bed and breakfast, each room is uniquely decorated featuring private baths, air conditioning and heat, cable t.v. Come join us for your special occasion or a... View all property information
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    Key West, Florida Keys 33040
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    1 / 27
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Hot Tub
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    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
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    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • 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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 28, 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed March 30, 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    Key West, Florida Keys 33040
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    1 / 10
    4.5 of 5 stars (34) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (34) Make Inquiry
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    • Air Conditioning
    • Balcony
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
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    • Suitable for children
    • x
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    • ?
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    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 30, 2014
    Nice two bedroom condo, well furnished, great location. Would definitely stay here again. Becky and her staff at the rental company were a pleasure to work with.
    4 of 5 stars Reviewed June 24, 2013
    BMW Fantasy was an excellent vacation rental. While a little dated, the pictures of the unit don't do it justice. It was clean, well kept and super convenient. Outside of the...
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    $1,500
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    1 / 14
    4.5 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Gym
    • 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. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 14, 2013
    Overall the condo is very nice. Towels and sheets could use an update along with all of the kitchen amenities. Mainly pots, pans, silverware etc. overall the place worked out...
    2 of 5 stars Reviewed April 4, 2013
    First off, we are not the type of people looking for a 4star place on a beer budget, then trash the accommodations on trip advisor because a lamp was out or the water tasted...
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    1 / 10
    4 of 5 stars (55) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 27, 2014
    Our rental was clean, with plenty of supplies and towels. It was in a gated area and we always felt very safe. I loved sitting on the patio outside, enclosed by foliage so it...
    5 of 5 stars Reviewed September 2, 2013
    It was close to walk to Duval Street and short drive or walk if you like to Fort Zachary Taylor state park for swimming at the beach.
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    1 / 15
    4.5 of 5 stars (37) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 13, 2013
    Lobster Fest was a blast! We had a great time and loved being on Duval Street, but far enough away from the main strip. The property was nice and well kept. Bathroom shower...
    4 of 5 stars Reviewed June 19, 2013
    Property is OK. Needs some maintenance and upgrades but overall acceptable, but not great. Good location if you want to be on Duval Street but away from the noise. Includes a...
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    1 / 13
    4.5 of 5 stars (41) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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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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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 21, 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 June 18, 2013
    very nice place in excellent location
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    1 / 11
    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...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 25, 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 May 31, 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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    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed May 18, 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Safe
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
    • ?
    About this property
    Key West has all of the charms of being away from the world, yet with all of the worldly conveniences near at hand. Located in the historic old town, Namaste Key West is in a quiet residential neighborhood, with beaches 5 minutes away, 3 yoga studios within a block, coffee shops, and a grocery... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 2, 2014
    My husband and I stayed in lovely Namaste from May 15th through Aug 15th and were enchanted the entire time. The house is lovely, even better than the fabulous pictures. It is...
    5 of 5 stars Reviewed April 30, 2013
    The Namaste Cottage was an amazing place to stay during our time in Key West. We spent two weeks at Namaste and were constantly reminded of how central it is to all of the great...
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Private Outdoor...
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
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    1 / 21
    4.5 of 5 stars (28) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 8, 2013
    Great place for singles And families. Easy access to entertainment and even Publix, Walgreens, restaurants everything! staff great, Highly Recommend! gorgeous view
    1 of 5 stars Reviewed April 30, 2013
    We have been going to Pelican Landing for the past several years. This has been the best experience so far. Any concerns we had were addressed immediately and the pool looks great...
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    4.5 of 5 stars (27) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Dishwasher
    • Grill
    • Internet Access
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    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 25, 2015
    We were pleased with the spacious accommodations at the Harbor Island Retreat. The rooms were clean and they (and view) were as depicted on the TA web site. The unit was...
    4 of 5 stars Reviewed November 27, 2014
    Not close to Duvall Street where everything is happening bit we enjoyed it and the unit was nicely decorated and had everything we needed. Huge balcony overlooking pool with a...
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    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 12, 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 June 12, 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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    1 / 25
    4.5 of 5 stars (43) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 13, 2015
    We loved Ann Street Gardens! A block from Duval 2 blocks from the historic seaport. In the middle of it all but as quiet as can be! The gardens, the pool, the home, all...
    5 of 5 stars Reviewed November 5, 2014
    My wife and I wanted a private getaway and the Ann Street house was just what the doctor ordered. The place was immaculate and just as important; quiet. We stocked the fridge...
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    4.5 of 5 stars (31) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Truman Annex. Decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. First floor features open living/dining area, kitchen and half bath. Kitchen is well... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 5, 2015
    The Foundry in Truman annex is where I stay every time I vacation in KW- close to everything but quiet & peaceful for relaxation.
    4 of 5 stars Reviewed January 22, 2014
    We stayed in a condo in the Truman annex Foundry this vacation, and we really loved the location. We could walk easily to the Key West Bight, the Mallory Square area, the...
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    1 / 15
    4.5 of 5 stars (47) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • 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
    • ?
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    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. 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.... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 2, 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    5 of 5 stars Reviewed August 1, 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    1 / 17
    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 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 March 17, 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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    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    ISLAND BREEZE: Located in the exclusive Sanctuary within the Key West Golf Club, this is a spacious home with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half-bath and living room, with French doors leading outside to the private deck. Upstairs offers the... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 6, 2013
    I try to avoid the winter in the northeast as much as possible and this house in the sanctuary made my life a lot easier this year. The home is beautiful and I would recommend...
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    4.5 of 5 stars (24) Very good
    Studio / 1 Bathroom / Sleeps 2
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 25, 2015
    Had a great time in Key West and this place made it all possible! First of all, it is within a block or two of Duval St. Staying that close was important to us because we wanted...
    5 of 5 stars Reviewed October 24, 2012
    We loved this place. We travel with out camper but thought staying in old town would be a good choice. We were right. We stored the camper and parked the van (one of the few...
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
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    1 / 24
    4.5 of 5 stars (15) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 8, 2014
    We rented this 4 bedroom 3 bath house for vacation with our adult children, 6 month old grandson and 87 year old father. It was perfect! One bedroom downstairs for Grandpa, a...
    5 of 5 stars Reviewed March 10, 2014
    We loved the privacy and security of the house. All family members enjoyed the quiet time at the house and the party atmosphere within walking distance. We had day trips and...
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    RENTAL RATES ARE NEGOTIABLE ......please contact us for current pricing and availability (we do not maintain calendars) In the event you, or your family, your guests, or your friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 30, 2014
    My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
    5 of 5 stars Reviewed June 22, 2014
    This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
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    4.5 of 5 stars (11) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
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    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 14, 2015
    Truman House was a joy! Location was perfect - convenient to everything. Pool was wonderful. Lots of living space - front porch, back deck, living room and a nice gathering...
    5 of 5 stars Reviewed April 13, 2015
    We are frequent visitors to Key West, where we usually get a tiny hotel room and spend all of our time out of the room. For a special occasion, we brought the kids, spouses, and a...
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 26, 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
    5 of 5 stars Reviewed May 25, 2015
    It was a fun and unique vacation! At first it took some getting used to, flushing the toilets, water supply, close quarters, etc. But by the end that's what made it memorable. The...
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (7) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 14, 2015
    Strongly recommended for families, very nice backyard, private pool that you cannot get your children out of it, perfect location. But beware of mosquitos at the evening...
    5 of 5 stars Reviewed April 28, 2015
    I've been going to Key West for the past 10yrs, and have stayed all over the island. I was looking for a place for a long weekend (sometimes hard to come by in EYW bc lots of...
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    4 of 5 stars (5) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** 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... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 24, 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St. Everything...
    5 of 5 stars Reviewed February 6, 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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    3.5 of 5 stars (9) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • x
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    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed March 3, 2015
    The property could use some updating. A little paint and some updated furniture would do wonders. Towels without rust and bleach stains should be considered. But we are used to...
    3 of 5 stars Reviewed December 14, 2014
    My family (a group of 9) stayed here for a week while in Key West for a wedding. Amelia's Hideaway was...ok. The rooftop deck and poolside patio were perfect for sitting outside...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    Key West, Florida Keys 33040
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    $4,650
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 29, 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 23, 2015
    While the Artist Cottage was not available, the owner had another Shipyard condo that was perfect for us. The property is nicely maintained, the pool clean and warm, and the...
    5 of 5 stars Reviewed June 29, 2014
    Wonderful location was able to walk to experience Key West. Something for everyone to enjoy with 2 older teenagers. Did something every day but was very relaxing, never felt...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 23, 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
    5 of 5 stars Reviewed November 1, 2013
    Really enjoyed the comfort of the unit. Close to everything but no need to leave!
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Ocean Views
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    History buffs love to immerse themselves in the centuries old legends of Key West – and if they're lucky, they'll find room in Smuggler's Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the island. Smuggler's Den, a delightfully... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (33) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Gym
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    • Sauna
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    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 27, 2015
    Depending on why you are going to Key West, this is an excellent choice. The apartments are fabulous and well decorated with everything you need. It is close enough to the...
    5 of 5 stars Reviewed March 25, 2015
    Great value for money. I am not a hot tub fan so this was not important to me. The weather did not cooperate but this did not matter as we were having such a great time.
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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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
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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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    Key West, Florida Keys 33040
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    $289
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    1 / 12
    4.5 of 5 stars (7) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Suitable for children
    • x
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    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 24, 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
    5 of 5 stars Reviewed July 9, 2014
    I went down to Key West with my husband, 2 year old son, and baby sitter. This cottage was perfect for us. The bedrooms (both upstairs) were comfortable and both had great...
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    5 of 5 stars (20) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
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    • x
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    • x
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    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 12, 2015
    Atlantis House is a very special hideaway. It is called a guest house, and we were truly the guests of Steve and Kayla. They were so welcoming from the day we arrived: helping...
    5 of 5 stars Reviewed November 30, 2014
    Steve, and Kayla, our Hosts, met us when we arrived, and from that moment on we felt like we were visiting family. Our room was immaculat , well appointed and warm. Kayla prepared...
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Part of TROPICAL VILLAGE Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $138
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    4 of 5 stars (1) Very good
    Studio / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • 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
    Part of Southernmost Sanctuary Suites The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 28, 2014
    Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each morning...
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    Key West Vacation Rentals and Condos

    Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

    Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

    Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

    Where To Rent a Vacation Home in Key West

    Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. 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.

    Many House Rentals Near Attractions and Activities For All Ages

    Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

    Key West Bars and Restaurants

    Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. 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.

    Book a Key West Vacation Rental For Your Next Trip

    Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.