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Vacation Rentals in Florida Keys

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  • 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 970 Rentals in Florida Keys
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From
$106
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Reviews (1) Make Enquiry
From
$4,833
Per Week
Marathon
4 Bedrooms, 5 Bathrooms, Sleeps 10
24 photos Details
Reviews (1) Make Enquiry
From
$537
Per Night
Matecumbe Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (2) Make Enquiry
Also consider
Pineapple Plantation
5 Bedrooms, sleeps 10
$23,628 / month
REDUCED END OF SUMMER/FALL RATES! CHARMING KEY COLONY BEACH POOL COTTAGE- MA753
2 Bedrooms, sleeps 4
$184 - $276 / night
Elegant Florida Keys Living, Family Friendly
2 Bedrooms, sleeps 4
$1,070 - $1,458 / week
You Private Beach Paradise!
2 Bedrooms, sleeps 7
$276 / night
From
$3,222
Per Month
Islamorada
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (1) Make Enquiry
From
$150
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
7 photos Details
Reviews (10) Make Enquiry
From
$375
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
1 photo Details
Reviews (1) Make Enquiry
From
$784
Per Night
Marathon
5 Bedrooms, 6 Bathrooms, Sleeps 10
15 photos Details
Reviews (1) Make Enquiry
From
$291
Per Night
Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
Reviews (1) Make Enquiry
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From
$215
Per Night
Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (2) Make Enquiry
From
$967
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
47 photos Details
Reviews (5) Make Enquiry
From
$263
Per Night
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 9
30 photos Details
Reviews (2) Make Enquiry
From
$247
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 7
28 photos Details
Reviews (5) Make Enquiry
From
$247
Per Night
Matecumbe Key
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (3) Make Enquiry
From
$460
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (2) Make Enquiry
From
$858
Per Night
Marathon
8 Bedrooms, 6 Bathrooms, Sleeps 20
24 photos Details
Reviews (1) Make Enquiry
From
$268
Per Night
Islamorada
Studio, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (18) Make Enquiry
From
$215
Per Night
Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (9) Make Enquiry
From
$258
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Reviews (2) Make Enquiry
From
$160
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
66 photos Details
Reviews (25) Make Enquiry
From
$118
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 8
7 photos Details
Reviews (1) Make Enquiry
From
$363
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
28 photos Details
Reviews (2) Make Enquiry
From
$967
Per Week
Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (2) Make Enquiry
From
$140
Per Night
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (5) Make Enquiry
From
$134
Per Night
Grassy Key
Studio, 1 Bathroom, Sleeps 2
27 photos Details
Reviews (1) Make Enquiry
From
$859
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
34 photos Details
Reviews (3) Make Enquiry
From
$183
Per Night
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
45 photos Details
Reviews (2) Make Enquiry
From
$215
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
From
$295
Per Night
Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (3) Make Enquiry
From
$169
Per Night
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (3) Make Enquiry
From
$185
Per Night
Big Pine Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
Reviews (7) Make Enquiry
From
$193
Per Night
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (1) Make Enquiry
From
$3,222
Per Month
Long Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Enquiry
From
$171
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 4
28 photos Details
Reviews (17) Make Enquiry
From
$1,450
Per Week
Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Enquiry
From
$1,047
Per Week
Big Pine Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (2) Make Enquiry
From
$430
Per Night
Matecumbe Key
3 Bedrooms, 3 Bathrooms, Sleeps 5
17 photos Details
Reviews (5) Make Enquiry
From
$145
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
14 photos Details
Reviews (1) Make Enquiry
From
$349
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
59 photos Details
Reviews (7) Make Enquiry
From
$295
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (24) Make Enquiry
From
$134
Per Night
Grassy Key
Studio, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (1) Make Enquiry
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Suitability

  • Wheelchair access (82)
  • Elder access (352)
  • Suitable for children (441)
  • Pet friendly (258)
  • Smoking allowed (10)

Amenities

  • Internet (758)
  • Other outdoor space (757)
  • Air Conditioning (752)
  • Grill (620)
  • All pools (516)
  • 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.