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Holiday Villas Florida Keys, FL

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
Response Rate: 95%
Marathon
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details
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From
$197
Per Night
Response Rate: 93%
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 6
17 photos Details
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From
$128
Per Night
Response Rate: 93%
Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
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Also consider
Beautiful Captain's Cove
3 Bedrooms, sleeps 8
$319 / night
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3 Bedrooms, sleeps 6
$266 / night
Key Colony Beach Condo Paradise - Private Beach!
2 Bedrooms, sleeps 4
$167 - $183 / night
Ocean Front Condo on Sandy Beach in center FL Keys
2 Bedrooms, sleeps 6
$167 - $205 / night
From
$455
Per Night
Response Rate: 92%
Marathon
2 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (4) Make Enquiry
From
$455
Per Night
Response Rate: 92%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (2) Make Enquiry
From
$850
Per Night
Response Rate: 92%
Marathon
8 Bedrooms, 6 Bathrooms, Sleeps 20
24 photos Details
Reviews (1) Make Enquiry
From
$303
Per Night
Response Rate: 92%
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
Reviews (1) Make Enquiry
From
$1,377
Per Week
Response Rate: 92%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (1) Make Enquiry
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From
$1,230
Per Night
Response Rate: 92%
Marathon
12 Bedrooms, 8 Bathrooms, Sleeps 30
6 photos Details
Reviews (1) Make Enquiry
From
$424
Per Night
Response Rate: 92%
Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
Reviews (5) Make Enquiry
From
$410
Per Night
Response Rate: 92%
Marathon
4 Bedrooms, 2 Bathrooms, Sleeps 8
15 photos Details
Reviews (10) Make Enquiry
From
$607
Per Night
Response Rate: 92%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 4
27 photos Details
Reviews (10) Make Enquiry
From
$222
Per Night
Response Rate: 92%
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (1) Make Enquiry
From
$190
Per Night
Response Rate: 92%
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details
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From
$160
Per Night
Response Rate: 92%
Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
$275
Per Night
Response Rate: 92%
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 6
27 photos Details
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From
$158
Per Night
Response Rate: 92%
Key Largo
Studio, 1 Bathroom, Sleeps 3
28 photos Details
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From
$266
Per Night
Response Rate: 92%
Marathon
2 Bedrooms, 1 Bathroom, Sleeps 6
15 photos Details
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From
$399
Per Night
Response Rate: 92%
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 10
12 photos Details
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From
$2,973
Per Week
Response Rate: 92%
Marathon
4 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
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From
$371
Per Night
Response Rate: 90%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
1 photo Details
Reviews (1) Make Enquiry
From
$777
Per Night
Response Rate: 90%
Marathon
5 Bedrooms, 6 Bathrooms, Sleeps 10
15 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
Response Rate: 90%
Grassy Key
Studio, 1 Bathroom, Sleeps 2
27 photos Details
Reviews (1) Make Enquiry
From
$293
Per Night
Response Rate: 90%
Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (3) Make Enquiry
From
$133
Per Night
Response Rate: 90%
Grassy Key
Studio, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (1) Make Enquiry
From
$186
Per Night
Response Rate: 90%
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
10 photos Details
Reviews (5) Make Enquiry
From
$452
Per Night
Response Rate: 90%
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (3) Make Enquiry
From
$465
Per Night
Response Rate: 90%
Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
5 photos Details
Reviews (1) Make Enquiry
From
$163
Per Night
Response Rate: 90%
Marathon
2 Bedrooms, 1 Bathroom, Sleeps 4
2 photos Details
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From
$244
Per Night
Response Rate: 90%
Key West
Studio, 1 Bathroom, Sleeps 2
11 photos Details
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From
$319
Per Night
Response Rate: 90%
Key Largo
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
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From
$532
Per Night
Response Rate: 90%
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
7 photos Details
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From
$346
Per Night
Response Rate: 90%
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
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From
$186
Per Night
Response Rate: 90%
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
6 photos Details
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From
$213
Per Night
Response Rate: 90%
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
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From
$775
Per Night
Response Rate: 90%
Marathon
5 Bedrooms, 6 Bathrooms, Sleeps 12
9 photos Details
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From
$360
Per Night
Response Rate: 90%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details
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From
$356
Per Night
Response Rate: 90%
Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
5 photos Details
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From
$140
Per Night
Response Rate: 90%
Marathon
Studio, 1 Bathroom, Sleeps 2
4 photos Details
Make Enquiry
From
$360
Per Night
Response Rate: 90%
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details
Make Enquiry
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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.