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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 970 Rentals in Florida Keys
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From
$206
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Outdoor Pool (Heated), Pet friendly, Grill & more
33 photos Details
Reviews (16) Make Enquiry
From
$266
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Washer/Dryer, Housekeeping Optional, Grill & more
6 photos Details
Reviews (1) Make Enquiry
From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Other outdoor space, Washer/Dryer & more
12 photos Details
Reviews (9) Make Enquiry
Also consider
Sunshine Luxury Suite - 2 Free Bicycles & Garage
2 Bedrooms, sleeps 6
$198 - $275 / night
Florida Keys' Jewel - Executive Bay Club
2 Bedrooms, sleeps 8
$105 - $373 / night
Elegant Bay Harbour Condo with 50 Foot Boat Slip
3 Bedrooms, sleeps 6
$334 - $533 / night
Villa Marlin, Renovated, Remodeled , Sandy Beach
3 Bedrooms, sleeps 6
$410 - $441 / night
From
$293
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Hot Tub, Grill & more
25 photos Details
Reviews (24) Make Enquiry
From
$266
Per Night
Studio, 1 Bathroom, Sleeps 2
Private Fishing Lake/River, Housekeeping Optional & more
13 photos Details
Reviews (18) Make Enquiry
From
$1,038
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Internet, Grill & more
10 photos Details
Reviews (2) Make Enquiry
From
$399
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Air Conditioning, Suitable for children, Parking & more
14 photos Details
Reviews (5) Make Enquiry
From
$152
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Public pool, Other outdoor space, Hot Tub & more
8 photos Details
Reviews (1) Make Enquiry
Get the List
From
$138
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Other outdoor space, Housekeeping Optional & more
29 photos Details
Reviews (2) Make Enquiry
From
$426
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
Air Conditioning, Internet, Boat Available & more
17 photos Details
Reviews (4) Make Enquiry
From
$245
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Internet, Air Conditioning, Washer/Dryer & more
28 photos Details
Reviews (5) Make Enquiry
From
$240
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
Internet, Grill, Washer/Dryer & more
15 photos Details
Reviews (1) Make Enquiry
From
$346
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Washer/Dryer, Parking, Suitable for children & more
59 photos Details
Reviews (7) Make Enquiry
From
$320
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Internet, Elder access, Pool & more
42 photos Details
Reviews (4) Make Enquiry
From
$2,769
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
Suitable for children, Housekeeping Optional & more
40 photos Details
Reviews (6) Make Enquiry
From
$112
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (1) Make Enquiry
From
$959
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Suitable for children, Private Fishing Lake/River & more
25 photos Details
Reviews (37) Make Enquiry
From
$852
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Internet, Other outdoor space, Air Conditioning & more
30 photos Details
Reviews (33) Make Enquiry
From
$224
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Water Views, Elder access & more
13 photos Details
Reviews (5) Make Enquiry
From
$213
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Internet, Other outdoor space, Washer/Dryer & more
8 photos Details
Reviews (2) Make Enquiry
From
$426
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Parking, Air Conditioning, Other outdoor space & more
24 photos Details
Reviews (1) Make Enquiry
From
$495
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Water Views, Air Conditioning, Grill & more
18 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Canoe, Air Conditioning, Elder access & more
10 photos Details
Reviews (1) Make Enquiry
From
$382
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 5
Water Views, Public pool, Fitness Room & more
21 photos Details
Reviews (9) Make Enquiry
From
$266
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Suitable for children
4 photos Details
Reviews (2) Make Enquiry
From
$320
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Private Outdoor Pool (Heated), Garden, Grill & more
15 photos Details
Reviews (6) Make Enquiry
From
$852
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Elder access, Pet friendly, Private pool & more
34 photos Details
Reviews (3) Make Enquiry
From
$186
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Washer/Dryer, Waterfront, Wi-Fi & more
37 photos Details
Reviews (7) Make Enquiry
From
$224
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Elder access, Public pool & more
6 photos Details
Reviews (2) Make Enquiry
From
$240
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Hot Tub, Internet, Air Conditioning & more
13 photos Details
Reviews (21) Make Enquiry
From
$240
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Internet, Suitable for children, Pet friendly & more
14 photos Details
Reviews (10) Make Enquiry
From
$137
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Elder access, Grill & more
12 photos Details
Reviews (3) Make Enquiry
From
$334
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Grill, Private Beach, Hot Tub & more
12 photos Details
Reviews (5) Make Enquiry
From
$4,793
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
Internet, Other outdoor space, Grill & more
22 photos Details
Reviews (3) Make Enquiry
From
$186
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Water Views, Parking, Grill & more
12 photos Details
Reviews (3) Make Enquiry
From
$274
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Boat Available, Internet, Water Views & more
10 photos Details
Reviews (5) Make Enquiry
From
$151
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Air Conditioning, Grill, Pool & more
19 photos Details
Reviews (31) Make Enquiry
From
$3,674
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 12
Air Conditioning, Internet, Parking & more
12 photos Details
Reviews (4) Make Enquiry
From
$166
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Water Views, Other outdoor space, Washer/Dryer & more
19 photos Details
Reviews (5) Make Enquiry
From
$309
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Internet, Pet friendly, Housekeeping Optional & more
26 photos Details
Reviews (12) 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.