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.

Holiday rentals in Florida Keys

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
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 1,119 Rentals in Florida Keys
loading...
Sort by
From
£92
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (3) Make Enquiry
From
£161
Per Night
Response Rate: 100%
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
26 photos Details
Reviews (1) Make Enquiry
From
£128
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (1) Make Enquiry
Also consider
Just Off Duval 3 Bedroom Private Home with Pool
3 Bedrooms, sleeps 6
£292 / night
Quiet Open Water On Wild Life Sanctuary
2 Bedrooms, sleeps 4
£817 / week
Gerry's Florida House
2 Bedrooms, sleeps 6
£200 / night
Fisherman's Paradise with a 30 Ft Boat Slip
3 Bedrooms, sleeps 8
£76 - £146 / night
From
£73
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 1 Bathroom, Sleeps 7
12 photos Details
Make Enquiry
From
£3,795
Per Month
Response Rate: 100%
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Make Enquiry
From
£333
Per Night
Response Rate: 100%
Key West
4 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Make Enquiry
From
£3,036
Per Week
Response Rate: 100%
Key West
3 Bedrooms, 4 Bathrooms, Sleeps 8
25 photos Details
Make Enquiry
From
£1,606
Per Month
Response Rate: 100%
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Make Enquiry
Get the List
From
£1,043
Per Night
Response Rate: 100%
Marathon
8 Bedrooms, 5 Bathrooms, Sleeps 20
22 photos Details
Make Enquiry
From
£204
Per Night
Response Rate: 100%
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details
Make Enquiry
From
£110
Per Night
Response Rate: 100%
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
Make Enquiry
From
£286
Per Night
Response Rate: 100%
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
61 photos Details
Make Enquiry
From
£3,211
Per Month
Response Rate: 100%
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Make Enquiry
From
£3,795
Per Month
Response Rate: 100%
Key West
5 Bedrooms, 3 Bathrooms, Sleeps 18
23 photos Details
Make Enquiry
From
£57
Per Night
Response Rate: 100%
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
25 photos Details
Make Enquiry
From
£1,460
Per Month
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
Make Enquiry
From
£11,620
Per Month
Response Rate: 100%
Key West
5 Bedrooms, 5 Bathrooms, Sleeps 14
40 photos Details
Make Enquiry
From
£5,401
Per Month
Response Rate: 100%
Key West
3 Bedrooms, 4 Bathrooms, Sleeps 8
21 photos Details
Make Enquiry
From
£2,482
Per Month
Response Rate: 100%
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
15 photos Details
Make Enquiry
From
£151
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Make Enquiry
From
£145
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 2
10 photos Details
Make Enquiry
From
£1,460
Per Month
Response Rate: 100%
Key West
1 Bedroom, 1 Bathroom, Sleeps 6
17 photos Details
Make Enquiry
From
£2,920
Per Month
Response Rate: 100%
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 8
26 photos Details
Make Enquiry
From
£759
Per Week
Response Rate: 100%
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
19 photos Details
Make Enquiry
From
£92
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 4
12 photos Details
Make Enquiry
From
£238
Per Night
Response Rate: 100%
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 10
19 photos Details
Reviews (1) Make Enquiry
From
£156
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Make Enquiry
From
£3,795
Per Month
Response Rate: 100%
Key West
3 Bedrooms, 4 Bathrooms, Sleeps 10
20 photos Details
Make Enquiry
From
£156
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Make Enquiry
From
£166
Per Night
Response Rate: 100%
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Make Enquiry
From
£92
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 4
16 photos Details
Make Enquiry
From
£92
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 4
12 photos Details
Make Enquiry
From
£221
Per Night
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (1) Make Enquiry
From
£81
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 2
12 photos Details
Make Enquiry
From
£934
Per Week
Response Rate: 100%
Marathon
1 Bedroom, 1 Bathroom, Sleeps 2
28 photos Details
Make Enquiry
From
£81
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 2
8 photos Details
Make Enquiry
From
£110
Per Night
Response Rate: 100%
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Make Enquiry
From
£221
Per Night
Response Rate: 100%
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 10
37 photos Details
Make Enquiry
From
£92
Per Night
Response Rate: 100%
Key West
Studio, 1 Bathroom, Sleeps 4
14 photos Details
Make Enquiry
From
£1,460
Per Month
Response Rate: 100%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Make Enquiry
Go to map view
Book Online(442)
Use filters to find the best results!

Suitability

  • Wheelchair access (80)
  • Elder access (351)
  • Suitable for children (440)
  • Pet friendly (294)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (899)
  • Internet (884)
  • Other outdoor space (837)
  • Grill (735)
  • All pools (656)
  • 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
Florida Keys Vacation Rentals

Relaxing in a hammock under a swaying palm tree. Sipping a margarita. Enjoying a cheeseburger in paradise. Life in the Florida Keys is unique, laid-back and fun. Spending your stay in a cramped, sterile hotel room just doesn’t seem to fit the lifestyle. You should consider a vacation rental. We’ll help you find special deals on beach houses, condos, townhouses, cottages and cabins in a variety of settings in Key Largo, Marathon, Islamorada, Big Pine Key and the Lower Keys, Key West and other locales. Better still, you’ll have lots of space to spread out and relax as well as a fully-equipped kitchen where you can fix the perfect margarita.

Florida Keys attractions and activities

From phenomenal scuba diving and snorkeling to world-class ocean sportfishing and flats fishing to eco-tours and sunset watch parties, the Florida Keys has something for everyone. Each section of the Keys has its own unique attractions. In Key Largo, visit John Pennekamp Coral Reef State Park, a spectacular undersea park. In Islamorada, the Theater of the Sea Marine Mammal Park, offers opportunities to swim with dolphins and other creatures. At Marathon’s Crane Point, you can hike through a preserved tropical hardwood grove. In the Lower Keys, beach enthusiasts love the Bahia Honda State Park with its white sandy beaches. Key West is home to the Ernest Hemingway Home and Museum, the Key West Butterfly & Nature Conservatory and Mel Fisher’s Maritime Heritage Museum.

Live like a local in a Florida Keys rental

A vacation rental allows you the freedom to pursue the Florida Keys getaway perfect for you and your family. You’ll have ample space to store your fishing equipment, scuba and snorkeling gear, beach toys and other necessities for a great beach vacation. When it’s time to dine, a fully equipped kitchen allows you to save money and prepare a delicious meal that might even include the big fish you caught earlier in the day. With a vacation rental in the Florida Keys, you can stop imagining what it’s like to live there and actually do it for a short time.

Florida Keys vacation rentals for families

From Key Largo to Key West, we have an inventory of vacation rentals ideal for family getaways. We’ve got plenty of low-cost, budget-helping rentals that will allow you to spend money on things like swimming with dolphins or scuba diving instead of on a pricey hotel room.

Saving money on Florida Keys vacation rentals

Obviously, you want the best deal available to stay within your budget. Whether you want an amenity-rich beachfront estate home, a condo affording stunning sunset views or a cozy cottage or cabin, we have special deals and discounts in every price range.