Florida Keys holiday rentals

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Best Florida Keys holiday rentals

Most recommended holiday rentals in Florida Keys

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Reef House - Duck Key - Living room
Reef House
Duck Key, FL, United States
8.4Very Good(16)
$577+
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Conch Key Villas #1 If Fun, Fishing and Views are on Your List, Stay Here! - Duck Key - Patio
Conch Key Villas #1 If Fun, Fishing and Views are on Your List, Stay Here!
Duck Key, FL, United States
Free Wi-Fi
Pet friendly
$489+
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Conch Key Villas #4. Newly remodeled for a Fantastic Florida Keys Vacation! - Duck Key - Patio
Conch Key Villas #4. Newly remodeled for a Fantastic Florida Keys Vacation!
Duck Key, FL, United States
Free Wi-Fi
Pet friendly
$504+
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Tropical oasis near all the action with central AC & balcony - Duck Key - Living room
Tropical oasis near all the action with central AC & balcony
Duck Key, FL, United States
7.8Good(25)
$678+
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Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana Club Access - Duck Key - Living room
Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana Club Access
Duck Key, FL, United States
7.0Good(2)
Free Wi-Fi
Spa
$801+
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Villages at Hawks Cay Villa with Spa - Duck Key - Pool
Villages at Hawks Cay Villa with Spa
Duck Key, FL, United States
Free Wi-Fi
Pool
Spa
$636+
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Palm Villa Special With Cabana Club 3/3-3/6/25 - Duck Key - Pool
Palm Villa Special With Cabana Club 3/3-3/6/25
Duck Key, FL, United States
Free Wi-Fi
Pool
$612+
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Villa 5103 On Duck Key Boat Slip Available - Duck Key - Building
Villa 5103 On Duck Key Boat Slip Available
Duck Key, FL, United States
$712+
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Villa 5054 On Duck Key Boat Slip Available - Duck Key - Building
Villa 5054 On Duck Key Boat Slip Available
Duck Key, FL, United States
$723+
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Tropical Cottages - Marathon - Patio
Tropical Cottages
Marathon, FL, United States
8.1Very Good(546)
Parking
Free Wi-Fi
Pet friendly
$256+
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Seafarer Key Largo Resort And Beach - Key Largo - Patio
Seafarer Key Largo Resort And Beach
Key Largo, FL, United States
8.4Very Good(2200)
Parking
Free Wi-Fi
Pet friendly
$310+
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Old Wooden Bridge Resort & Marina - Big Pine Key - Living room
Old Wooden Bridge Resort & Marina
Big Pine Key, FL, United States
8.3Very Good(126)
Parking
Free Wi-Fi
Pool
Pet friendly
$324+
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Bay Harbor Lodge - Key Largo - Patio
Bay Harbor Lodge
Key Largo, FL, United States
9.3Wonderful(594)
Parking
Free Wi-Fi
Pool
$371+
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Colors On White - Key West - Bedroom
Colors On White
Old Town North of Truman
7.3Good(427)
Parking
Free Wi-Fi
Pool
Pet friendly
$393+
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Global Luxury Suites Miami Worldcenter - Miami - Bedroom
Global Luxury Suites Miami Worldcenter
Downtown
8.3Very Good(81)
Free Wi-Fi
Pool
Pet friendly
$341+
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Palm Breeze - Duck Key
Palm Breeze
Duck Key, FL, United States
8.7Very Good(16)
$509+
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Low season

October

High season

December

Average price (weeknight)

$757

Average price (weekend night)

$571
Cheapest month to stay with an average 17% drop in price.
Most expensive month to stay with an average 71% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Florida Keys holiday rental

FAQs when booking a holiday home in Florida Keys

  • How much is a holiday rental in Florida Keys for tonight?

    In the last 72 hours, users have found Florida Keys holiday rentals for tonight for as little as $105. Search here for similar prices

  • What types of holiday rentals are available in Florida Keys?

    There are loads of different property types that you can make your holiday home in Florida Keys. You’ll find boats, campgrounds, condos, houses, campsites, apartments, bungalows, cabins, caravans, cottages, lodges, motorhomes, houseboats, villas, towers, homestays, agritourism, chalets, luxury tents and caravan parks.

  • What are some of the most-loved holiday rentals available in Florida Keys?

    There are many types of properties available for Florida Keys holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Sun Outdoors Key Largo and Habitat Brickell by Sextant.

  • Are there any pet-friendly holiday rentals in Florida Keys?

    There are a number of dog and pet-friendly Florida Keys holiday rentals, with around 16% allowing you to bring your pet along with you.

Where to stay in Florida Keys?

Our map will help you find the perfect place to stay in Florida Keys by showing you the exact location of each holiday home.

What Florida Keys holiday rental guests are talking about

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Holiday rentals by topic

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Habitat Brickell by Sextant - Miami - Lounge
Habitat Brickell by Sextant
Brickell
8.1Very Good(1436)
Free Wi-Fi
Pool
$209+
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Hudson House - Miami
Hudson House
Miami, FL, United States
8.2Very Good(685)
Free Wi-Fi
$20+
Check availability
Four Ambassadors Apartments - Miami
Four Ambassadors Apartments
Brickell
7.8Good(157)
Free Wi-Fi
$251+
Check availability

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