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Vacation 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
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All 1,120 Rentals in Florida Keys
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From
$190
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (20) Make Enquiry
From
$222
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
Reviews (35) Make Enquiry
From
$320
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Reviews (40) Make Enquiry
Also consider
Holidays are fast approaching! Book Now!
3 Bedrooms, sleeps 6
$128 / night
Rare 2BR/2BA Shipyard Condo Truman Annex Old Town
2 Bedrooms, sleeps 6
$960 - $2,668 / week
Clarke's Condo - Key Largo, Florida
2 Bedrooms, sleeps 5
$149 / night
Islamorada Luxurie Retreat
2 Bedrooms, sleeps 4
$170 - $212 / night
From
$6,402
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 12
12 photos Details
Reviews (1) Make Enquiry
From
$179
Per Night
Key West
Studio, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (5) Make Enquiry
From
$3,094
Per Month
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
22 photos Details
Reviews (1) Make Enquiry
From
$283
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (31) Make Enquiry
From
$1,275
Per Week
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (2) Make Enquiry
Get the List
From
$190
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
Reviews (27) Make Enquiry
From
$190
Per Night
Key West
Studio, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (35) Make Enquiry
From
$265
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 6
14 photos Details
Reviews (20) Make Enquiry
From
$907
Per Week
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
21 photos Details
Reviews (7) Make Enquiry
From
$169
Per Night
Key West
Studio, 1 Bathroom, Sleeps 2
10 photos Details
Reviews (14) Make Enquiry
From
$286
Per Night
Key West
2 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details
Reviews (20) Make Enquiry
From
$158
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (23) Make Enquiry
From
$339
Per Night
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
15 photos Details
Reviews (7) Make Enquiry
From
$320
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 6
28 photos Details
Reviews (9) Make Enquiry
From
$190
Per Night
Key West
Studio, 1 Bathroom, Sleeps 2
10 photos Details
Reviews (4) Make Enquiry
From
$320
Per Night
Key Largo
4 Bedrooms, 4 Bathrooms, Sleeps 10
32 photos Details
Reviews (3) Make Enquiry
From
$240
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
34 photos Details
Reviews (15) Make Enquiry
From
$347
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (1) Make Enquiry
From
$147
Per Night
Key West
Studio, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (30) Make Enquiry
From
$361
Per Night
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (7) Make Enquiry
From
$319
Per Night
Key Largo
4 Bedrooms, 4 Bathrooms, Sleeps 10
33 photos Details
Reviews (6) Make Enquiry
From
$338
Per Night
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
36 photos Details
Reviews (3) Make Enquiry
From
$286
Per Night
Key West
2 Bedrooms, 3 Bathrooms, Sleeps 6
18 photos Details
Reviews (32) Make Enquiry
From
$640
Per Night
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
Reviews (1) Make Enquiry
From
$393
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (8) Make Enquiry
From
$848
Per Night
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
33 photos Details
Reviews (5) Make Enquiry
From
$453
Per Night
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details
Reviews (17) Make Enquiry
From
$2,774
Per Month
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (4) Make Enquiry
From
$1,067
Per Night
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 6
76 photos Details
Reviews (5) Make Enquiry
From
$800
Per Night
Key West
4 Bedrooms, 3 Bathrooms, Sleeps 10
21 photos Details
Reviews (4) Make Enquiry
From
$267
Per Night
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
8 photos Details
Reviews (1) Make Enquiry
From
$158
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
21 photos Details
Reviews (18) Make Enquiry
From
$133
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (4) Make Enquiry
From
$320
Per Night
Key West
4 Bedrooms, 3 Bathrooms, Sleeps 8
43 photos Details
Reviews (1) Make Enquiry
From
$156
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
64 photos Details
Reviews (12) Make Enquiry
From
$293
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
5 photos Details
Reviews (2) Make Enquiry
From
$347
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (1) Make Enquiry
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Suitability

  • Wheelchair access (80)
  • Elder access (351)
  • Suitable for children (441)
  • Pet friendly (294)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (900)
  • Internet (885)
  • Other outdoor space (838)
  • Grill (736)
  • All pools (656)
  • View all amenities
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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.