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

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 433 Rentals in Key West
loading...
Sort by
From
$6,525
Per Month
View Details
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
From
$249
Per Night
View Details
1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
From
$280
Per Night
View Details
1 / 28
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
From
$1,075
Per Night
View Details
1 / 25
5 Bedrooms, 6 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants, shops,... View all property information
Make Enquiry
From
$1,419
Per Night
View Details
1 / 28
6 Bedrooms, 7 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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
Make Enquiry
From
$305
Per Night
View Details
1 / 21
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
Make Enquiry
From
$1,800
Per Night
View Details
1 / 24
Payment Protection
11 Bedrooms, 9 Bathrooms, Sleeps 32
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE... View all property information
Make Enquiry
From
$93
Per Night
View Details
1 / 8
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
MONTHLY RENTAL ONLY Fantastic 2nd floor studio with a large private deck located just one block from famous duval street. This tree top studio is cozy. For your convenience there is a kitchennette with a 2 burner stove, microwave oven and a toaster oven. There is a brand new queen size sleeper sofa... View all property information
Make Enquiry
From
$309
Per Night
View Details
1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2013/14! We are located within Key West city limits in one Key West's only waterfront neighborhoods. We are about 4 miles from Duval Street and downtown, about 2 miles from Smather's Beach and the... View all property information
Make Enquiry
From
$14,915
Per Month
View Details
1 / 22
5 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
Get the List
From
$3,107
Per Month
View Details
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the... View all property information
Make Enquiry
From
$305
Per Night
View Details
1 / 14
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
Make Enquiry
From
$10,565
Per Month
View Details
1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
When I first toured this special Key West ~ Indies vacation house, I was struck by the refreshingly authentic blend of its multi-cultural exterior design and interior decor, and felt as if I could be standing in a villa in the British Virgin Islands (BVI). It's not surprising the home embodies this... View all property information
Make Enquiry
From
$261
Per Night
View Details
1 / 21
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
Make Enquiry
From
$435
Per Night
View Details
1 / 9
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
$2,610
Per Month
View Details
1 / 9
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation... View all property information
Make Enquiry
From
$218
Per Night
View Details
1 / 22
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start your day of... View all property information
Make Enquiry
From
$2,237
Per Week
View Details
1 / 11
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as 'Truman Annex', this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean... View all property information
Make Enquiry
From
$6,898
Per Month
View Details
1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
If you have ever had the fortune to wander the historic streets and lanes of Key West's famous seaport neighborhood then you know how time seems to stand still. Yet right in the heart of Key West's bustling seaport this blissfully ideal cottage-style house offers all the amenities one could desire... View all property information
Make Enquiry
From
$746
Per Night
View Details
1 / 15
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
$423
Per Night
View Details
1 / 37
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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
Make Enquiry
From
$373
Per Night
View Details
1 / 9
2 Bedrooms, 3 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Hidden from view at the end of a little lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this spectacular downtown Key West... View all property information
Make Enquiry
From
$211
Per Night
View Details
1 / 4
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the Southernmost Point, Hemingway House, Mallory Square, and the Historic Seaport. This... View all property information
Make Enquiry
From
$4,102
Per Week
View Details
1 / 15
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
$994
Per Night
View Details
1 / 18
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
$5,717
Per Month
View Details
1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage ideal for a quiet couple or single person with discerning taste. The property is the perfect Key West setting for rest, relaxation, and rejuvenation. It is ideal for the person of distinction who... View all property information
Make Enquiry
From
$2,890
Per Night
View Details
1 / 45
11 Bedrooms, 11 Bathrooms, Sleeps 24
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
Make Enquiry
From
$1,554
Per Night
View Details
1 / 40
9 Bedrooms, 7 Bathrooms, Sleeps 22
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
$249
Per Night
View Details
1 / 23
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full... View all property information
Make Enquiry
Enquire for rates
1 / 17
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
My home is in a quiet neighborhood, and just minutes away from all that Key West has to offer. Come relax and enjoy life on the island. Just a few moments walk to Smathers Beach, Higgs Beach, and close to local restaurants. With 3 bedrooms, 2 baths, a beautifully manicured front yard, pool,... View all property information
Make Enquiry
From
$18,643
Per Month
View Details
1 / 25
Payment Protection
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
If you’re looking for spacious downtown living, the Amethyst House will be your perfect getaway. As a monthly rental this property has everything you need to relax and enjoy the Key West island life! The home can accommodate 8, comfortably accommodating either a larger family down for an extended... View all property information
Make Enquiry
From
$3,107
Per Month
View Details
1 / 24
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic... View all property information
Make Enquiry
From
$638
Per Night
View Details
1 / 11
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large living room and dining room with a kitchen that overlooks your own patio. Lush... View all property information
Make Enquiry
Go to map view
Book Online(66)
Use filters to find the best results!

Suitability

  • Wheelchair access (23)
  • Elder access (71)
  • Suitable for children (13)
  • Pet friendly (170)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (385)
  • Other outdoor space (357)
  • Internet (341)
  • All pools (265)
  • Grill (248)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List