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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 1,120 Rentals in Florida Keys
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From
$532
Per Week
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (2) Make Enquiry
From
$2,447
Per Month
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (5) Make Enquiry
From
$479
Per Night
Sugarloaf Key
4 Bedrooms, 4 Bathrooms, Sleeps 8
31 photos Details
Reviews (8) Make Enquiry
Also consider
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
Sunshine Luxury Suite - 2 Free Bicycles & Garage
2 Bedrooms, sleeps 6
$198 - $274 / night
Hemmingway's Retreat
3 Bedrooms, sleeps 8
$399 / night
From
$3,723
Per Month
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (7) Make Enquiry
From
$4,787
Per Month
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Enquiry
From
$532
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details
Reviews (8) Make Enquiry
From
$341
Per Night
Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 12
12 photos Details
Reviews (6) Make Enquiry
From
$5,318
Per Month
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
17 photos Details
Reviews (2) Make Enquiry
Get the List
From
$185
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details
Reviews (1)
From
$170
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 7
29 photos Details
Reviews (9) Make Enquiry
From
$456
Per Night
Islamorada
4 Bedrooms, 3 Bathrooms, Sleeps 8
28 photos Details
Reviews (4) Make Enquiry
From
$257
Per Night
Ramrod Key
4 Bedrooms, 2 Bathrooms, Sleeps 8
14 photos Details
Reviews (6) Make Enquiry
From
$372
Per Night
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details
Reviews (12) Make Enquiry
From
$191
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 8
35 photos Details
Reviews (5) Make Enquiry
From
$231
Per Night
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 12
41 photos Details
Reviews (1) Make Enquiry
From
$213
Per Night
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Enquiry
From
$138
Per Night
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (5) Make Enquiry
From
$204
Per Night
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
43 photos Details
Reviews (7) Make Enquiry
From
$186
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (15) Make Enquiry
From
$266
Per Night
Long Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Reviews (2) Make Enquiry
From
$106
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$266
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
31 photos Details
Reviews (2) Make Enquiry
From
$1,330
Per Week
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (2) Make Enquiry
From
$745
Per Week
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (10) Make Enquiry
From
$106
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (2) Make Enquiry
From
$182
Per Night
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
38 photos Details
Reviews (4) Make Enquiry
From
$4,255
Per Month
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (5) Make Enquiry
From
$372
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (4) Make Enquiry
From
$372
Per Night
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Enquiry
From
$984
Per Week
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (1) Make Enquiry
From
$984
Per Week
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
15 photos Details
Reviews (2) Make Enquiry
From
$3,457
Per Week
Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Reviews (3) Make Enquiry
From
$213
Per Night
Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (2) Make Enquiry
From
$239
Per Night
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
13 photos Details
Reviews (16) Make Enquiry
From
$356
Per Night
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
Reviews (12) Make Enquiry
From
$335
Per Night
Islamorada
2 Bedrooms, 3 Bathrooms, Sleeps 8
30 photos Details
Reviews (5) Make Enquiry
From
$987
Per Night
Marathon
5 Bedrooms, 7 Bathrooms, Sleeps 12
28 photos Details
Reviews (5) Make Enquiry
From
$441
Per Night
Key Colony Beach
4 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (1) Make Enquiry
From
$160
Per Night
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Reviews (2) Make Enquiry
From
$181
Per Night
Matecumbe Key
1 Bedroom, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (16) 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.