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Holiday Villas Florida Keys, FL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
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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 1,119 Rentals in Florida Keys
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From
$137
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (3) Make Enquiry
From
$4,260
Per Month
Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
Reviews (1) Make Enquiry
From
$186
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (3) Make Enquiry
Also consider
Oceanfront views, all the amenities & boat dockage
2 Bedrooms, sleeps 8
$335 / night
Contemporary Bali-style Design -120ft sandy beach
5 Bedrooms, sleeps 12
$988 / night
The Sand Dollar - 4/3 Waterfront Pool House - KCB
4 Bedrooms, sleeps 8
$442 / night
2 bedroom 2 bath upgraded home  Key Largo Florida
2 Bedrooms, sleeps 6
$160 / night
From
$128
Per Night
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Reviews (2) Make Enquiry
From
$479
Per Night
Key West
4 Bedrooms, 3 Bathrooms, Sleeps 7
21 photos Details
Reviews (4) Make Enquiry
From
$2,769
Per Month
Key West
2 Bedrooms, 3 Bathrooms, Sleeps 4
20 photos Details
Reviews (3) Make Enquiry
From
$151
Per Night
Key Colony Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (31) Make Enquiry
From
$639
Per Night
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
Reviews (1) Make Enquiry
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From
$186
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
10 photos Details
Reviews (5) Make Enquiry
From
$303
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
22 photos Details
Reviews (1) Make Enquiry
From
$682
Per Night
Marathon
4 Bedrooms, 2 Bathrooms, Sleeps 10
35 photos Details
Reviews (1) Make Enquiry
From
$201
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (6) Make Enquiry
From
$319
Per Night
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
32 photos Details
Reviews (11) Make Enquiry
From
$274
Per Night
Conch Key
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (5) Make Enquiry
From
$197
Per Night
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (6) Make Enquiry
From
$266
Per Night
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 8
6 photos Details
Reviews (1) Make Enquiry
From
$334
Per Night
Grassy Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (5) Make Enquiry
From
$166
Per Night
Key Colony Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Reviews (5) Make Enquiry
From
$240
Per Night
Duck Key
2 Bedrooms, 3 Bathrooms, Sleeps 6
30 photos Details
Reviews (9) Make Enquiry
From
$4,473
Per Week
Marathon
5 Bedrooms, 4 Bathrooms, Sleeps 14
1 photo Details
Reviews (1) Make Enquiry
From
$532
Per Night
Islamorada
4 Bedrooms, 5 Bathrooms, Sleeps 8
50 photos Details
Reviews (2) Make Enquiry
From
$149
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
Reviews (38) Make Enquiry
From
$200
Per Night
Key West
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Reviews (3) Make Enquiry
From
$2,662
Per Month
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (8) Make Enquiry
From
$453
Per Night
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (3) Make Enquiry
From
$985
Per Week
Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (2) Make Enquiry
From
$5,325
Per Month
Islamorada
2 Bedrooms, 1 Bathroom, Sleeps 4
26 photos Details
Reviews (2) Make Enquiry
From
$457
Per Night
Islamorada
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
Reviews (3) Make Enquiry
From
$266
Per Night
Key Largo
4 Bedrooms, 2 Bathrooms, Sleeps 8
4 photos Details
Reviews (2) Make Enquiry
From
$206
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (7) Make Enquiry
From
$228
Per Night
Conch Key
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (11) Make Enquiry
From
$133
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (3) Make Enquiry
From
$250
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
Reviews (2) Make Enquiry
From
$1,597
Per Night
Key West
10 Bedrooms, 6 Bathrooms, Sleeps 20
42 photos Details
Reviews (23) Make Enquiry
From
$319
Per Night
Key West
4 Bedrooms, 3 Bathrooms, Sleeps 8
43 photos Details
Reviews (1) Make Enquiry
From
$346
Per Night
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
Reviews (8) Make Enquiry
From
$114
Per Night
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (13) Make Enquiry
From
$137
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
21 photos Details
Reviews (1) Make Enquiry
From
$309
Per Night
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (43) Make Enquiry
From
$373
Per Night
Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
28 photos Details
Reviews (16) Make Enquiry
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Book Online(442)
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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
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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.