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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room,... View all property information
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    Key West, Florida Keys 33040
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 14, 2015
    Location was superb. Staff at Compass / Truman Annex Reality (Michelle) were easy to work with and very accommodating. Owner was very pleasurable and great to work with. Overall...
    5 of 5 stars Reviewed May 13, 2015
    Fully equipped, comfortable, clean, family home with the use of a community pool. During our stay in May (when it was very warm) there were only ever a few at the pool which was...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Just like its name, Petunia is a happy place. Open the picket gate, walk down the short, bricked walk and open the original wood door with a grin from ear to ear. You’ve come home. This two-story, two-bedroom home with a beautifully updated, second-floor bath offers the kinds of privacy and... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
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    About this property
    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 9, 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed February 26, 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 28, 2015
    We very much enjoyed this condo. It is beautifully decorated and there is a high priority for safety. Each condo has a private elevator that can only be entered with a specific...
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    1 / 22
    4 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 20, 2013
    I chose the Pelican Landing due its proximity to Duvall Street and the ability to secure the rental for daily rates. The unit was spacious and had a lot of accommodations within...
    5 of 5 stars Reviewed June 16, 2013
    I was very happy and impressed with the conda that I stayed at,,, It was very clean,spacious and had very nice view
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ***BRAND NEW POOL COMPLETED SEPTEMBER 2015*** Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $8,500
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    • Shared Yard
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    About this property
    When I first toured this special Key West ~ Indies vacation house, I was struck by the refreshingly authentic blend of its multi-cultural exterior design and interior decor, and felt as if I could be standing in a villa in the British Virgin Islands (BVI). It's not surprising the home embodies this... View all property information
    Location Information
    Key West, Florida Keys
    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $255
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    • Balcony
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    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed June 27, 2015
    Great place and nice location to Mallory Square. Not too far of a walk to Blue Heaven which is a must. The pool was very nice and very clean. The Banana Key is a great condo that...
    5 of 5 stars Reviewed January 16, 2013
    We chose Banana Key just a few days before we actually got there due to a last minute vacation opportunity. I worked with Tim at Historic Hideways and couldn't have been happier...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    $215
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    • Satellite TV
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    • Porch
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $1,750
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • Elder access
    • x
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    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. Bright, tropical colors and tile floors provide an island ambience to... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 27, 2014
    This unit has recently been refreshed and is very comfortable. It has everything you need to have a perfect vacation. The kitchen is well stocked, if you are inclined to do some...
    4 of 5 stars Reviewed May 2, 2013
    The location was great, Smathers beach is awesome and right across the street. we were a short bike ride from everything. The rental agency was great and very responsive. The unit...
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    1 / 26
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom features a king-size bed, flat screen television, en suite bathroom and french doors leading you out to the private side deck. The second bedroom features a queen-size bed and flat screen... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed July 28, 2014
    Our stay at Paradise Palms was truly a month in paradise. The house was just the right size with new interior and appliances. The location is in a nice neighborhood that was a...
    4 of 5 stars Reviewed March 3, 2014
    great house, nice location. Would be perfect if there was a pool. Fantastic private outdoor shower. We were there for a month and for the money, it should have included a cleaning...
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    1 / 26
    5 of 5 stars (27) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 30, 2015
    We loved our stay at Casa del Sol. The location was perfect for sight seeing and walking everywhere. We never used our car for the week's stay. The beds were comfortable, the...
    5 of 5 stars Reviewed August 31, 2015
    Casa del Sol is in a perfect location in Key West with an easy 2 block walk to Duvall Street but in a quiet relaxing residential area. The condo is very clean, well equipped and...
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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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. Additional amenities include: sofabed, coffee maker, nearby beach, nearby bank, nearby internet cafe, ice maker, near beach, nearby medical... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 15, 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 the...
    5 of 5 stars Reviewed June 13, 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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    1 / 25
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed May 20, 2015
    My husband and I absolutely loved everything about this place! It was everything we expected. Clean, comfortable, and great location. If I could change one thing it would be...
    5 of 5 stars Reviewed May 20, 2015
    Great location! Great deck! Very spacious. We loved it here. Best part...it's so quiet! The pool was great too. We usually had it to ourselves. Walking distance to everything.
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 2014
    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 3, 2011
    We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
    5 of 5 stars Reviewed January 27, 2011
    Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard...
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    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    First floor corner condo perfect for 2 plus space for visiting friends and family! A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    We needed a place to stay for a month and boy are we glad we found this one! Close enough to walk to everything, yet in a very secluded and quiet area. Comes with an off street...
    4 of 5 stars Reviewed April 26, 2014
    Very nice condo with huge pool area. Very clean and neat. We loved the location! We would love to go back again some day. The only negative was the living room furniture. It...
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    1 / 19
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Child-friendly
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    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed December 3, 2013
    3 of us rented a condo in the foundry located in the Truman annex. I have stayed here before and knew what to expect. Any unit in Truman annex is an easy walk to everything...
    4 of 5 stars Reviewed March 15, 2013
    Had a great time. Historic Hideaways was very helpful. Our place was central to everything, very clean. Perfect for our needs. Thank you.
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    1 / 25
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed September 18, 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    5 of 5 stars Reviewed May 12, 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described as... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 4, 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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    1 / 19
    4 of 5 stars (6) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer. Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 8, 2014
    Super-cute house, adorably decorated, with nice bathrooms & a great Viking range for when you're eating in. Great location in Bahama Village.
    5 of 5 stars Reviewed December 26, 2013
    Fishtail Hideaway is located in a quiet neighborhood only 2 blocks from Duval St. We loved being able to walk to the beach, the Southernmost Point, plenty of shopping and the...
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    1 / 13
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 9, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    $309
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    • Internet Access
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    • Child-friendly
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (35) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Child-friendly
    • x
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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 June 16, 2015
    This 2 bed room condo is very clean, spacious and has what you need in the kitchen, extra linens, towels and beach towels for the pool. The 2 bedrooms are on the 2nd floor and...
    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.
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    1 / 26
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
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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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 30, 2013
    What could be better in Key West than your own pool, adorable kitchen and updated baths, and a great location, a few blocks from Duval. Kw Vacation Rentals couldn't have been...
    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...
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    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Live in the lap of luxury in this stunningly renovated Key West classic 'Eyebrow House.' An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed June 16, 2015
    My husband and I spent 3 months in this beautiful conch style eyebrow house. The pictures do not do it justice. The gorgeous yard with the pool, palms, mahogany trees and deck...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    About this property
    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around Wilmington town or shopping, eating and drinking your way down to the board walk on front street .... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4.5 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $3,500
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    • Internet Access
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    • Pet-friendly
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    • x
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    About this property
    Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is filled with quality, style and class throughout. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 14, 2012
    Great Time
    3 of 5 stars Reviewed April 13, 2011
    Shower temperature is practically uncontrollable. It suddenly goes cold for 1+ minutes. Several light bulbs were burned out when I arrived. The location is very convenient. But it...
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    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed October 31, 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    1 / 32
    3 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Part of TROPICAL VILLAGE Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 7, 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute...
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    1 / 24
    4.5 of 5 stars (27) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    This gracious one bedroom, one bath conch cottage with private pool is the perfect place for your dream vacation. Casablanca is set back from White Street which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. The... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 4 weeks ago
    Cute little bungalow that's well maintained with a private pool and fenced in yard. Walking distance to Mallory Square 20 min's, it's located in a quieter area but close to...
    5 of 5 stars Reviewed October 1, 2015
    The Casablanca House was a perfect little place for my husband and I for the 5 days that we stayed in Key West. It was clean and very comfortable. It is close to a grocery store...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 3, 2013
    I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
    5 of 5 stars Reviewed February 19, 2013
    Ellen´s retreat was simply fantastic. The house was beautiful and luxurious. The grounds were spacious and it was like you had your very own private oasis. I need also to mention...
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • ?
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    • Elder access
    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed March 2, 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 13, 2015
    Located in the historic Old Town section of Key West, this is one of three units in one building. The owner lives in the front and their friend in the middle unit, both were very...
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    1 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 3, 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    5 of 5 stars Reviewed December 18, 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    1 / 15
    4.5 of 5 stars (38) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    I have stayed here many years in a row for Christmas and New years and Have loved everyday. A LARGE 2 story condo right on Duval street for this price. You cant beat it. We drive...
    4 of 5 stars Reviewed September 11, 2013
    The property location is good, just realize where it is compared to any activities you plan. The buildings themselves are undergoing some type of renovation on the outside, not...
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    1 / 14
    4.5 of 5 stars (61) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $250
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    • Terrace
    • DVD Player
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    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • Elder access
    • x
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    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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 15, 2015
    Four friends and I stayed six very relaxing nights here. The owner and management team quickly responded to inquiries. The property (interior and exterior) was very clean, well...
    4 of 5 stars Reviewed June 17, 2014
    We traveled in a group and the home was very accommodating with 3 bedrooms and 3 bathrooms as well as from and rear downstairs and upstairs balconies. The furniture was...
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    1 / 12
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $120
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    • Waterfront
    • Air Conditioning
    • Grill
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    • Hot Tub
    • Washer
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 4-6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed September 3, 2014
    Location is quiet, couple blocks off Duval. The pool was great to beat the heat. Tracy very responsive. The only complaint is that the rooms are run down and also could use a...
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    1 / 23
    4 of 5 stars (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 2015
    Could be a great place . Needs a good deep cleaning and friendlier and more helpful women working in the office. Was there for 4 days with kids in November with no pool heater...
    5 of 5 stars Reviewed July 18, 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
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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.