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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
$213
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
26 photos Details
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From
$128
Per Night
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
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From
$854
Per Night
Key West
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
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Also consider
Seabird Key, Private Island Rental with Boat
3 Bedrooms, sleeps 8
$960 - $1,220 / night
Moon Bay on the ocean in legendary Key Largo
2 Bedrooms, sleeps 5
$144 / night
Key's Dreamin Oceanside House
3 Bedrooms, sleeps 6
$373 - $384 / night
La Casa Habana: Lovely 3BR Gulf house w/ pool,dock
3 Bedrooms, sleeps 8
$335 / night
From
$107
Per Night
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
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From
$1,056
Per Night
Islamorada
3 Bedrooms, 5 Bathrooms, Sleeps 8
29 photos Details
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From
$603
Per Night
Marathon
4 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
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From
$373
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 5
15 photos Details
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From
$375
Per Night
Key Largo
5 Bedrooms, 6 Bathrooms, Sleeps 12
17 photos Details
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From
$259
Per Night
Islamorada
2 Bedrooms, 3 Bathrooms, Sleeps 6
25 photos Details
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From
$347
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
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From
$4,588
Per Month
Key Largo
2 Bedrooms, 3 Bathrooms, Sleeps 10
36 photos Details
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From
$4,268
Per Month
Long Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
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From
$191
Per Night
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details
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From
$2,241
Per Month
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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From
$244
Per Night
Key West
Studio, 1 Bathroom, Sleeps 2
11 photos Details
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From
$778
Per Night
Marathon
5 Bedrooms, 6 Bathrooms, Sleeps 12
9 photos Details
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From
$160
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
9 photos Details
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From
$85
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
2 photos Details
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From
$267
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
$373
Per Night
Matecumbe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
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From
$848
Per Night
Islamorada
3 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details
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From
$534
Per Night
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
7 photos Details
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From
$229
Per Night
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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From
$289
Per Night
Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
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From
$320
Per Night
Key Largo
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
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From
$191
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
$114
Per Night
Ramrod Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
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From
$302
Per Night
Key Largo
4 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
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From
$347
Per Night
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 6
38 photos Details
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From
$320
Per Night
Sugarloaf Key
3 Bedrooms, 4 Bathrooms, Sleeps 6
20 photos Details
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From
$427
Per Night
Big Pine Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
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From
$213
Per Night
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
1 photo Details
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From
$2,134
Per Night
Tavernier
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
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From
$267
Per Night
Tavernier
3 Bedrooms, 3 Bathrooms, Sleeps 12
7 photos Details
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From
$117
Per Night
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 5
15 photos Details
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From
$240
Per Night
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
6 photos Details
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From
$320
Per Night
Tavernier
3 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
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From
$197
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 6
17 photos Details
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From
$1,067
Per Night
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
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From
$160
Per Night
Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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Book Online(443)
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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.