We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key West House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $446 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    Applied filters: Clear All
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
    Match
    House Rentals
    Show Prices
    Payment Protection
    1 / 19
    5 of 5 bubbles (15) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    1 / 25
    4 of 5 bubbles (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    1 / 43
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (7) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine. The large living area is decorated in charming vintage wallpaper and bright, tropical colors. To the left... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (39) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Patio
    • Grill
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    10% OFF already discounted prices for Open dates in MAY & JUNE 2017! Please call our office for details. This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Patio
    • Balcony
    • DVD Player
    • Terrace
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Terrace
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Central Heating
    • Washer
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (38) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin... View all property information
    Location Information
    Key West, Florida Keys 33040
    Get the List
    1 / 25
    5 of 5 bubbles (51) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Grill
    • Private Outdoor...
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    3.5 of 5 bubbles (10) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Washer
    • Outdoor Dining Area
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Mermaid Cove is a small island compound that is great for large groups or big families. It's made up of 2 apartments and 2 cottages with an intimate courtyard in the middle with BBQ grill and table, shaded by a massive mango tree. Located right on Duval Street, Mermaid is just a block and a half... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (55) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor...
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    3.5 of 5 bubbles (9) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    4.5 of 5 bubbles (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Grill
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (39) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    4 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled in one of Key West's original gated "mini-compounds," the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4 of 5 bubbles (42) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (42) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Parking
    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises when you walk inside. Villa Nouveau Key West vacation rental has an interesting story that attests to this truth. Once a prosaic 'shot-gun' style cottage, a modern redesign has... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Grill
    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Washer
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    OVERVIEW: Monthly Only. Right in Key West -- NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (20) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    3 of 5 bubbles (8) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 45
    4.5 of 5 bubbles (2) Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Satellite TV
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.  Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Parking
    • Satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4 of 5 bubbles (16) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Balcony
    • Terrace
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    10% OFF already discounted prices for Open dates MAY - JULY 2017! Please call our office for details. 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    House Rentals
    Show Prices
    Amenities & Details
    • Patio
    • Private Outdoor...
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    House Rentals
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Terrace
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca... View all property information
    Location Information
    Key West, Florida Keys 33040