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 Vacation 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.
Check In Check Out
    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}
    View Map
    Price
    per night
    $345 Average
    $0$1,000+
    Suitability
    More filters
    All 881 Rentals in Key West
    Sort by:
    Default
    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    1 Review
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    80 Reviews
    2 Bedrooms, Sleeps 5Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    1 Review
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy Key West with a unique experience to remember forever. Your water home, a 35' Sea Ray, is a moored (heavy duty anchors) boat in Key West with an unobstructed view of the boats & harbor, stars, and beautiful water. Access is provided by a short water taxi ride. I will help to escort you to the...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    2 Reviews
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West. 2200 sq. ft living area. This place is really incredible! it's one of the largest oceanfront suites in Key West. 3 bedroom, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    33 Reviews
    2 Bedrooms, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Sauna
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Scroll down to "About the owner" and in that box click on the "See more" button -...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    9 Reviews
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    10% OFF already discounted prices for Open dates in MAY & JUNE 2017! Please call our office for details. Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street,...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    45 Reviews
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • Satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident that this beautifully restored 19th century home with four bedrooms and two full baths is named "Island Time" in honor of that low-key feeling....
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Sauna
    • Air Conditioning
    • DVD Player
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    26 Reviews
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Balcony
    • DVD Player
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining,...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. NOTE: On this page, TripAdvisor might be showing the summer price. The price changes seasonally. We are booking **monthly** renters for May, September, and November. Sorry, no short rental periods. NOTE:...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    5 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for two families wanting to vacation together or large groups. This is a large duplex home with a total of 5 bdrms and 3.5 bathrooms: One side has 3 bdrms (two rooms with queen, one room with 2 twins) + 2 baths. The other side has 2 bdrms (one room with queen, one room with 2 twins) + 1.5...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To tee, or not to tee: that is the question ... But whether or not golf is your game, the Key West Golf and Country Club promises a stay in one of the most esthetical residential neighborhoods in the Florida Keys. Beyond the masterfully designed 18 hole golf course, here you’ll enjoy the 200 acres...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    41 Reviews
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    1 Review
    7 Bedrooms, Sleeps 18Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Balcony
    • Satellite TV
    • Patio
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 18
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern conveniences include a new...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    1 Review
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Sauna
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Yard
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    50 Reviews
    10 Bedrooms, Sleeps 22Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 10 Bedrooms, 6 Bathrooms, Sleeps 22
    Make Inquiry
    4 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Patio
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    39 Reviews
    4 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Terrace
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    1 Review
    1 Bedroom, Sleeps 2Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location!<BR><BR>Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided.<BR><BR>This property will meet all of the...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Waterfront
    • DVD Player
    • Satellite TV
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2nd FLOOR 2BR/2BA OCEANFRONT SUITE C-22 Rental for 1 week only: $3,750 (SLEEPS 6) / Week 2 / Jan 6-13, 2018 1 Master bedroom King - 1 Guest Room Queen - 1 Queen pullout / Sweeping view of ocean from Master Bedroom, Living room & Balcony just 40 ft away / Convenient spiral stair access from balcony...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    20 Reviews
    5 Bedrooms, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    3 Reviews
    4 Bedrooms, Sleeps 10Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Wi-Fi
    • Private Yard
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Genuine ‘old-world’ charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening clear heart pine from floor to 12 foot ceiling, the immaculate interior rooms radiate a warm and magical feel that would be nearly impossible to replicate by modern builders....
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    Make Inquiry
    27 Reviews
    2 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Terrace
    • Satellite TV
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Patio
    • Grill
    • Air Conditioning
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway. Sanctuary on Simonton was newly built in 2015. The paint is barely dry on these exquisite townhomes! Enter through the glass front door and find yourself...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a House Boat that is 45 feet long and 18 feet wide two story. The Boat House is located Sunset Marina over looking the Gulf Of Mexico. Fisherman paradise and couples paradise. You are just minutes for all of Key West excitement. The marina is very quite and the water is crystal clear. You...
    View all property information
    Location Information
    Key West, Florida Keys KEY WEST FL 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 private bedrooms, plus pullout bed. Immaculate cabin interior. Approximately 100 yards off shore is where your adventure begins! Enjoy key west sunshine on your own private sundeck with comfortable upholstered seating & outdoor table for drinks/snacks. After you've worked on your tan, venture...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    21 Reviews
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Balcony
    • Grill
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees....
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    • Patio
    • Balcony
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Inquiry
    Check In Check Out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Parking
    • Balcony
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RENTAL- 28 DAY MINIMUM Duval Square Delight is located in a quaint town home community just steps from Duval Street. Upstairs there are residential units and a rooftop pool, while downstairs there are shops and restaurants surrounded by cobblestones and mature, tropical landscaping. Duval...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Inquiry
    3 Reviews
    6 Bedrooms, Sleeps 16Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Inquiry
    15 Reviews
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • Patio
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    Key West Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    80° 70°
    May
    83° 73°
    June
    84° 74°
    July
    84° 74°
    August

    Additional Key West Info

    View Map
    • Local time: 10:27 PM (EDT)
    • Peak travel: March - April
    List your property
    Owner log in