Florida Keys holiday rentals

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Best Florida Keys holiday rentals

Most recommended holiday rentals in Florida Keys

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Ocean View with Pool, 4 bedroom Vila Near Key West - Cudjoe Key - Pool
Ocean View with Pool, 4 bedroom Vila Near Key West
Cudjoe Key, FL, United States
10Wonderful(3)
Parking
Free Wi-Fi
Pool
Pet-friendly
S$ 1,202+
Check availability
Grand Marina Suite -Waterfront Condo - Stock Island - Pool
Grand Marina Suite -Waterfront Condo
Stock Island, FL, United States
8.8Very Good(77)
Parking
Free Wi-Fi
Pool
S$ 870+
Check availability
Villa of the Setting Sun - Summerland Key
Villa of the Setting Sun
Summerland Key, FL, United States
9.0Wonderful(25)
Pool
S$ 4,197+
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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(121)
Parking
Free Wi-Fi
Pool
Pet-friendly
S$ 327+
Check availability
Waterfront Paradise At Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds - Summerland Key - Beach
Waterfront Paradise At Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds
Summerland Key, FL, United States
9.7Wonderful(38)
Free Wi-Fi
Pool
Spa
S$ 676+
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Cottage with Pool and Dockage, just minutes to Key West - Cudjoe Key - Patio
Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key, FL, United States
Pool
Pet-friendly
S$ 319+
Check availability
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West - Cudjoe Key - Balcony
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key, FL, United States
8.9Very Good(51)
Pool
Pet-friendly
S$ 607+
Check availability
Gated Community On Open Water With Dock, Heated Pool, Kayaks, Bikes - Cudjoe Key - Outdoor view
Gated Community On Open Water With Dock, Heated Pool, Kayaks, Bikes
Cudjoe Key, FL, United States
Free Wi-Fi
Pool
S$ 1,103+
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Beachside Unit 19 - Key Colony - Key Colony Beach - Beach
Beachside Unit 19 - Key Colony
Key Colony Beach, FL, United States
Pool
S$ 406+
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Yellow Vacation home Free cancelation see details - Cudjoe Key - Patio
Yellow Vacation home Free cancelation see details
Cudjoe Key, FL, United States
9.9Wonderful(26)
S$ 1,009+
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Oceania... Water Front Cottage Retreat ~ - Cudjoe Key - Dining room
Oceania... Water Front Cottage Retreat ~
Cudjoe Key, FL, United States
9.5Wonderful(18)
Parking
Free Wi-Fi
Pool
S$ 990+
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Sugarloaf Lodge - Sugarloaf Shores - Pool
Sugarloaf Lodge
Sugarloaf Shores, FL, United States
7.4Good(1041)
Parking
Free Wi-Fi
Pool
Pet-friendly
S$ 243+
Check availability
Significantly Discounted!! 45' Sea Ray Yacht Located In 5 Star Resort! - Stock Island - Living room
Significantly Discounted!! 45' Sea Ray Yacht Located In 5 Star Resort!
Stock Island, FL, United States
Free Wi-Fi
S$ 502+
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub - Summerland Key - Outdoor view
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
Summerland Key, FL, United States
Pool
S$ 453+
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Quaint Glamping Cottage on Private Island, Sandy Beach with Freshwater Pool! - Marathon - Outdoor view
Quaint Glamping Cottage on Private Island, Sandy Beach with Freshwater Pool!
Marathon, FL, United States
Free Wi-Fi
Pool
S$ 568+
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Fiesta Key Rv Resort Standard Room 8 - Long Key
Fiesta Key Rv Resort Standard Room 8
Long Key, FL, United States
8.5Very Good(71)
Parking
S$ 266+
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Flexible cancellationFree breakfastFree parkingFree internet

Good to know

Low season

August

High season

December

Average price (weeknight)

S$ 564

Average price (weekend night)

S$ 435
Cheapest month to stay with an average 12% drop in price.
Most expensive month to stay with an average 90% 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 S$ 48. Search here for similar prices

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

    In the last 72 hours, users have found Florida Keys holiday rentals for this weekend for as little as S$ 97 per night. 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?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Tropical Cottages.

  • 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.

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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
S$ 227+
Check availability
Hudson House Miami - Miami
Hudson House Miami
Miami, FL, United States
8.2Very Good(685)
Free Wi-Fi
S$ 16+
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Four Ambassadors Apartments - Miami
Four Ambassadors Apartments
Brickell
7.7Good(158)
Free Wi-Fi
S$ 195+
Check availability

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