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.

Vacation Rentals in Key West, FL

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
    $403 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 20
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 32
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 30
    4 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 27
    4.5 of 5 bubbles (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Parking
    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool...
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Terrace
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    5 of 5 bubbles (3) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Hot Tub
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... 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 / 31
    4.5 of 5 bubbles (2) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Grill
    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 36
    3.5 of 5 bubbles (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ***Both bathrooms and kitchen completely renovated as of September, 2015*** Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Ocean Views
    • DVD Player
    • Housekeeping...
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    4.5 of 5 bubbles (10) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
    Location Information
    Key West, Florida Keys
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Hot Tub
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Terrace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 2 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be better!... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 35
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    Get the List
    1 / 25
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    With its rich wood flooring and triple windows, this selection is truly fit for a king. Wood and cane furnishings and metal sculpted palm lamps with intricate shell shades make the guest feel welcome and relaxed. Double nightstands and a writer's desk add to the atmosphere without compromising... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Satellite TV
    • Internet Access
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 bubbles (3) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southern Palms ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of the TROPICAL VILLAGE COMPOUND Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Terrace
    • Balcony
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Cozy Condo in Prime Location! Right off of Duval Street! Located just steps off of world famous Duval Street, Duval Canopy is the perfect blend of comfort, location and value. Just a few blocks from The Southernmost Beach, the Southernmost Point, and other favorites like The Butterfly Conservatory... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Terrace
    • Internet Access
    • Shared Outdoor Pool...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Paradise Palms is decorated in a tropical motif, with a palm matelassé and herb-green pinstriped bed skirt. There are wood furnishings throughout, along with nautical prints and souvenirs. Double doors open onto our second story landing where you are only steps away from the upper sun deck of our... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • Balcony
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Terrace
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This 1 bed 1 bath apartment with a balcony over looking Duval St. is perfect for anyone traveling to Key West. Its prime location puts you within walking distance to Southernmost Point, Mallory Square, shops, restaurants, and the famous Key West nightlife. With Dade County Pine walls and island... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful motor yacht is available for your exquisite Key West vacation! . Huge Salon, Large galley, gorgeous teak throughout. One queen bedroom and one full bedroom with bathrooms for each one. Forward on the bow are 2 very comfortable loungers with pillows for relaxing. The upper deck is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Banana's Foster Guesthouse. This cute and colorful studio is perfect for anyone who is excited to explore Key West on a budget. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Terrace
    • Balcony
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Hot Tub
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    3.5 of 5 bubbles (8) Average
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa. The bedroom has a queen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This property has a 7 night minimum due to HOA rules :) Welcome to Truman Tranquility - the perfect vacation rental for family & friends alike. The living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private patio, which features... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (2) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Grill
    • Hot Tub
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Porch
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Hot Tub
    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Recently updated!) Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Tropical Breeze is decorated in a tropical motif, with a cozy palm frond matelassé. There are wood and wicker furnishings throughout. Traditional Key West shutters allow the floral scents and chirping of birds to drift through the room. The door opens onto our second story landing where you are... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4 of 5 bubbles (27) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Shared Outdoor Pool...
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 52
    5 of 5 bubbles (14) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
    Location Information
    Key West, Florida Keys 33040