Winter Vacation Rentals & Cabin Rentals in Key Largo, FL

Compare 2,820 available oceanfront holiday vacation home properties, starts from $25

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Key Largo, FL: Top Deals

Waterside Suites and Marina
Waterside Suites and Marina
Waterside Suites and Marina
Waterside Suites and Marina
Waterside Suites and Marina
Waterside Suites and Marina
Waterside Suites and Marina
4.3 (451 reviews)
Waterside Suites and Marina
Hotel
$125 /night
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Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo
4.0 (205 reviews)
Courtyard by Marriott Key Largo
Hotel
$144 /night
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LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
4.7 (3 reviews)
LICENSED MGR - 3/3 MODERN LAGOONFRONT VILLA - OCEANFRONT BEACH RESORT!
Villa
$350 /night
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Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
Paradise Getaway **
4.0 (1 review)
Paradise Getaway **
Apartment · 6 Guests · 2 Bedrooms
$399 /night*
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The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
The Real Liveaboard Experience. Cruise Included
5.0 (7 reviews)
The Real Liveaboard Experience. Cruise Included
Yacht · 4 Guests · 2 Bedrooms
$699 /night*
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LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
4.7 (3 reviews)
LICENSED MGR - MODERN 3/3.5 VILLA - KEY LARGO'S MOST UPSCALE OCEANFRONT RESORT!
Villa
$450 /night
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Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
Kawama Yacht Club Apartment
4.8 (8 reviews)
Kawama Yacht Club Apartment
Apartment
$225 /night
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Sunset Cove Beach Resort
Sunset Cove Beach Resort
Sunset Cove Beach Resort
Sunset Cove Beach Resort
Sunset Cove Beach Resort
Sunset Cove Beach Resort
Sunset Cove Beach Resort
4.3 (376 reviews)
Sunset Cove Beach Resort
Resort
$114 /night
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Vitamin Sea
Vitamin Sea
Vitamin Sea
Vitamin Sea
Vitamin Sea
Vitamin Sea
Vitamin Sea
4.2 (9 reviews)
Vitamin Sea
Hotel
$77 /night
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Similar Inspirational Vacation Rental Destinations

How Does The Vacation Home Rental Price Look Like in Key Largo, FL?
Vacation House & Condo Rental Price Information in Key Largo, FL
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The graph shows the percentages of vacation homes in each price bucket. Key Largo has the largest percentage (21.44%) of homes in $150 - $200 price range.
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What are some of the best activities, places or communities for snowbirds to visit in Key Largo, FL?
Snowbirds Friendly Places and Activities in Key Largo, FL
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Key Largo is an ideal place for snowbirds. Located in beautiful South Florida, it offers a variety of activities and attractions that appeal to winter visitors. It has a mild climate with temperatures that rarely drop below 65 degrees Fahrenheit. The area provides access to numerous attractions such as beaches, fishing, diving, shopping, restaurants, and more. In addition, there are many health care facilities nearby, making this an excellent destination for seniors.

  • John Pennekamp Coral Reef State Park

    John Pennekamp Coral Reef State Park is the only underwater park in the US. It's a great spot for snorkeling and scuba diving, with plenty of colorful coral reefs and wildlife to explore. There are also kayaking and glass-bottom boat tours available, perfect for those who want to take in the seascape without getting wet.

  • Theater of the Sea

    Theater of the Sea is a marine mammal attraction offering interactive programs with dolphins, sea lions, stingrays, and other animals. It's a great way to learn about these amazing creatures while having fun. There are also dolphin encounters, shark dives, and boat tours available.

  • Dagney Johnson Key Largo Hammock Botanical State Park

    Dagney Johnson Key Largo Hammock Botanical State Park is a nature preserve with a variety of habitats, including mangrove swamps, hardwood hammocks, and pinelands. It's a great place to go bird watching and see some of the rare plants and animals that call the Keys home.

How Many Accommodations Are Pets Allowed in Key Largo, FL?
Pets Allowed vs Not Allowed in Key Largo, FL
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19.93% of vacation homes in Key Largo are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Where Should We Visit in Key Largo, FL Area?
Destinations To Visit During the Winter in Key Largo, FL
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