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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
$96
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Internet, Washer/Dryer, Air Conditioning & more
20 photos Details
Reviews (6) Make Enquiry
From
$533
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 6
Other outdoor space, Internet, Hot Tub & more
12 photos Details
Reviews (2) Make Enquiry
From
$480
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Parking, Fireplace, Water Views & more
31 photos Details
Reviews (8) Make Enquiry
Also consider
Direct Oceanfront Luxury Getaway w/ Pool & Dockage
5 Bedrooms, sleeps 12
$724 - $1,142 / night
Key Largo Paradise Point- Waterfront Pool Home
3 Bedrooms, sleeps 6
$255 / night
Ocean View, Great boat access,Short Walk to Beach,
3 Bedrooms, sleeps 8
$256 / night
Great location close to popular Sombrero Beach
3 Bedrooms, sleeps 8
$2,132 - $2,505 / week
From
$185
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Public pool, Pool, Heated Pool & more
16 photos Details
Reviews (1)
From
$533
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Suitable for children, Internet, Washer/Dryer & more
10 photos Details
Reviews (8) Make Enquiry
From
$457
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Parking & more
27 photos Details
Reviews (4) Make Enquiry
From
$4,264
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Grill, Internet & more
29 photos Details
Reviews (1) Make Enquiry
From
$149
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Tennis Court, Public pool & more
25 photos Details
Reviews (23) Make Enquiry
Get the List
From
$373
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Garden, Water Views, Elder access & more
24 photos Details
Reviews (12) Make Enquiry
From
$192
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Public pool, Water Views, Parking & more
35 photos Details
Reviews (5) Make Enquiry
From
$171
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Internet, Suitable for children, Water Views & more
29 photos Details
Reviews (9) Make Enquiry
From
$342
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 12
Parking, Other outdoor space, Internet & more
12 photos Details
Reviews (6) Make Enquiry
From
$187
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Elder access, Internet, Shared Outdoor Pool (Heated) & more
17 photos Details
Reviews (15) Make Enquiry
From
$267
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Washer/Dryer, Air Conditioning, Grill & more
31 photos Details
Reviews (2) Make Enquiry
From
$213
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Pet friendly, Boat Available, Other outdoor space & more
15 photos Details
Reviews (2) Make Enquiry
From
$231
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
Private Pool, Heated Pool, Other outdoor space & more
41 photos Details
Reviews (1) Make Enquiry
From
$267
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Water Views, Other outdoor space, Hot Tub & more
23 photos Details
Reviews (2) Make Enquiry
From
$373
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Parking, Water Views, Internet & more
19 photos Details
Reviews (1) Make Enquiry
From
$213
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Washer/Dryer, Parking, Grill & more
12 photos Details
Reviews (1) Make Enquiry
From
$139
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Other outdoor space, Parking, Grill & more
24 photos Details
Reviews (5) Make Enquiry
From
$5,330
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 8
Grill, Other outdoor space, Pet friendly & more
24 photos Details
Reviews (1) Make Enquiry
From
$986
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Grill, Public pool & more
20 photos Details
Reviews (1) Make Enquiry
From
$986
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 5
Pool, Public pool, Parking & more
15 photos Details
Reviews (2) Make Enquiry
From
$182
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Washer/Dryer, Parking, Other outdoor space & more
38 photos Details
Reviews (4) Make Enquiry
From
$1,333
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Internet, Air Conditioning, Other outdoor space & more
11 photos Details
Reviews (2) Make Enquiry
From
$3,465
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
Elder access, Other outdoor space, Water Views & more
30 photos Details
Reviews (4) Make Enquiry
From
$181
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Other outdoor space, Private Beach, Water Views & more
28 photos Details
Reviews (16) Make Enquiry
From
$205
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Grill, Other outdoor space, Internet & more
43 photos Details
Reviews (7) Make Enquiry
From
$107
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Waterfront, Internet & more
25 photos Details
Reviews (2) Make Enquiry
From
$114
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Suitable for children, Internet & more
15 photos Details
Reviews (11) Make Enquiry
From
$240
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Internet, Public pool, Air Conditioning & more
13 photos Details
Reviews (16) Make Enquiry
From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children, Air Conditioning & more
5 photos Details
Reviews (2) Make Enquiry
From
$138
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Water Views, Private Outdoor Pool (Heated) & more
88 photos Details
Reviews (63) Make Enquiry
From
$258
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Beach, Water Views, Grill & more
14 photos Details
Reviews (6) Make Enquiry
From
$336
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Shared Outdoor Pool (Heated), Public pool, Internet & more
30 photos Details
Reviews (5) Make Enquiry
From
$159
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Private Beach, Grill, Suitable for children & more
66 photos Details
Reviews (25) Make Enquiry
From
$357
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Wheelchair access, Housekeeping Optional & more
23 photos Details
Reviews (12) Make Enquiry
From
$442
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Water Views, Parking, Grill & more
14 photos Details
Reviews (1) Make Enquiry
From
$144
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Elder access, Air Conditioning & more
20 photos Details
Reviews (17) Make Enquiry
From
$106
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Internet, Public pool, Washer/Dryer & more
22 photos Details
Reviews (1) Make Enquiry
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Book Online(447)
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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.