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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 1,051 Rentals in Florida Keys
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From
$185
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Public pool, Pool, Heated Pool & more
16 photos Details
Reviews (1)
From
$96
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Internet, Washer/Dryer, Air Conditioning & more
20 photos Details
Reviews (6) Make Enquiry
From
$373
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Water Views, Pet friendly, Internet & more
31 photos Details
Reviews (2) Make Enquiry
Also consider
seaside haven
1 Bedroom, sleeps 4
$106 / night
Just Off Duval 3 Bedroom Private Home with Pool
3 Bedrooms, sleeps 6
$532 / night
East of Eden
3 Bedrooms, sleeps 6
$457 / night
Luxury vacation rental minutes from Key West
3 Bedrooms, sleeps 8
$277 - $319 / night
From
$5,323
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 8
Grill, Other outdoor space, Pet friendly & more
24 photos Details
Reviews (1) Make Enquiry
From
$985
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 5
Pool, Public pool, Parking & more
15 photos Details
Reviews (2) Make Enquiry
From
$985
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Grill, Public pool & more
20 photos Details
Reviews (1) Make Enquiry
From
$105
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Internet, Public pool, Washer/Dryer & more
22 photos Details
Reviews (1) Make Enquiry
From
$434
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
24 photos Details
Reviews (1) Make Enquiry
Get the List
From
$4,791
Per Month
3 Bedrooms, 1 Bathroom, Sleeps 1
Waterfront, Internet, Grill & more
23 photos Details
Reviews (4) Make Enquiry
From
$4,258
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Grill, Internet & more
29 photos Details
Reviews (1) Make Enquiry
From
$3,194
Per Month
1 Bedroom, 1 Bathroom, Sleeps 4
Washer/Dryer, Internet, Private Beach & more
11 photos Details
Reviews (1) Make Enquiry
From
$1,065
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Grill, Air Conditioning, Internet & more
22 photos Details
Reviews (1) Make Enquiry
From
$465
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
5 photos Details
Reviews (1) 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
$777
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 10
Suitable for children, Water Views, Hot Tub & more
15 photos Details
Reviews (1) Make Enquiry
From
$254
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Fitness Room, Air Conditioning, Hot Tub & more
13 photos Details
Reviews (13) Make Enquiry
From
$254
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Fitness Room, Other outdoor space, Hot Tub & more
13 photos Details
Reviews (8) Make Enquiry
From
$135
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Elder access, Parking, Shared Outdoor Pool (Heated) & more
24 photos Details
Reviews (3) Make Enquiry
From
$289
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 12
Internet, Water Views, Grill & more
11 photos Details
Reviews (1) Make Enquiry
From
$3,194
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children, Pet friendly
15 photos Details
Reviews (1) Make Enquiry
From
$69
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Elder access, Internet, Air Conditioning & more
23 photos Details
Reviews (3) Make Enquiry
From
$151
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Suitable for children, Wheelchair access & more
9 photos Details
Reviews (1) Make Enquiry
From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Internet, Air Conditioning, Parking & more
12 photos Details
Reviews (3) Make Enquiry
From
$12,775
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Other outdoor space, Internet & more
17 photos Details
Reviews (2) Make Enquiry
From
$106
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Waterfront, Internet & more
25 photos Details
Reviews (2) Make Enquiry
From
$96
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Pet friendly, Other outdoor space & more
34 photos Details
Reviews (10) Make Enquiry
From
$192
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Internet, Air Conditioning, Garden & more
15 photos Details
Reviews (1) Make Enquiry
From
$168
Per Night
Studio, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (1) Make Enquiry
From
$117
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Suitable for children, Boat Available & more
7 photos Details
Reviews (1) Make Enquiry
From
$213
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Other outdoor space, Housekeeping Optional, Garden & more
35 photos Details
Reviews (1) Make Enquiry
From
$95
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Internet, Other outdoor space, Air Conditioning & more
25 photos Details
Reviews (3) Make Enquiry
From
$229
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Elder access, Washer/Dryer, Public pool & more
15 photos Details
Reviews (1) Make Enquiry
From
$1,437
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Elder access, Public pool & more
22 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
Studio, 1 Bathroom, Sleeps 2
Internet, Other outdoor space, Washer/Dryer & more
27 photos Details
Reviews (1) Make Enquiry
From
$236
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Suitable for children, Public pool & more
21 photos Details
Reviews (1) Make Enquiry
From
$106
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Water Views, Parking, Other outdoor space & more
14 photos Details
Reviews (17) Make Enquiry
From
$958
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Private Fishing Lake/River, Boat Available & more
47 photos Details
Reviews (5) Make Enquiry
From
$213
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Air Conditioning, Other outdoor space & more
12 photos Details
Reviews (1) 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
$293
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Parking, Shared Outdoor Pool (Heated) & more
27 photos Details
Reviews (3) Make Enquiry
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Book Online(450)
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Suitability

  • Wheelchair access (90)
  • Elder access (352)
  • Suitable for children (444)
  • Pet friendly (284)
  • Smoking allowed (12)

Amenities

  • Air Conditioning (834)
  • Other outdoor space (834)
  • Internet (819)
  • Grill (690)
  • All pools (550)
  • 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.