Key West, FL holiday rentals

Holiday Rentals in Key West, FL

2307 available vacation rental offers

2 1
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Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Key West, FL

Tranquility By Avantstay | Close To Duval St W/ Bbq & Shared Pool - Key West, FL
9.6Excellent 81 reviews
Key West, FL
2 1
£503/nighttotal: £2012 (4 )

Tranquility By Avantstay | Close To Duval St W/ Bbq & Shared Pool

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Key West
Helen's Hideaway - Key West, FL
8.9Very good 92 reviews
Key West, FL
6 2
£1268/nightfor 1 night

Helen's Hideaway

house
Key West
Southernmost Sanctuary - Key West, FL
8.8Very good 1993 reviews
Key West, FL
2 1
£443/nighttotal: £2215 (5 )

Southernmost Sanctuary

hotel
Key West
Duval Sea Turtle By Avantstay | Great Location | Close To Shops | Shared Pool! - Key West, FL
9.5Excellent 237 reviews
Key West, FL
5 2
£544/nighttotal: £1632 (3 )

Duval Sea Turtle By Avantstay | Great Location | Close To Shops | Shared Pool!

apartment
Key West
Pier House Resort & Spa - Key West, FL
8.7Very good 7393 reviews
Key West, FL
8 2
£1595/nighttotal: £6380 (4 )

Pier House Resort & Spa

resort
Key West
Hyatt Centric Key West Resort & Spa - Key West, FL
8.7Very good 2914 reviews
Key West, FL
8 2
£2135/nighttotal: £8540 (4 )

Hyatt Centric Key West Resort & Spa

resort
Key West
Windward Isle - Key West, FL
9.0Excellent 523 reviews
Key West, FL
3 2
£487/nighttotal: £974 (2 )

Windward Isle

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Key West
Private Tanning Pier! 4 Modern Units By The Beach, 3 Onsite Pools, Beach Access - Key West, FL
8.2Very good 1972 reviews
Key West, FL
2 1
£395/nighttotal: £790 (2 )

Private Tanning Pier! 4 Modern Units By The Beach, 3 Onsite Pools, Beach Access

resort
Key West
Eisenhower Retreat: Conch Style Home In Oldtown With Private Pool And Dock! - Key West, FL
9.8Excellent 195 reviews
Key West, FL
2 4
£1322/nighttotal: £6610 (5 )

Eisenhower Retreat: Conch Style Home In Oldtown With Private Pool And Dock!

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Key West
Sunrise Suites Paradise Escape #407 - Key West, FL
8.8Very good 160 reviews
Key West, FL
6 2
£414/nighttotal: £828 (2 )

Sunrise Suites Paradise Escape #407

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Key West
Brisa Del Mar By Avantstay Communal Pool Gated Community Ocean Front - Key West, FL
9.2Excellent 85 reviews
Key West, FL
2 1
£605/nighttotal: £2420 (4 )

Brisa Del Mar By Avantstay Communal Pool Gated Community Ocean Front

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Key West
Conch Casa - Key West, FL
9.2Excellent 345 reviews
Key West, FL
6 2
£518/nighttotal: £1036 (2 )

Conch Casa

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Key West

Other types of accommodation in Key West, FL

Best Key West, FL holiday rentals with a pool

Among the 2307 accommodations in Key West, FL, here are the 8 best rentals with a pool

Sunrise Suites Tierra Bomba Suite #403 - Key West, FL
8.3Very good 319 reviews
Key West, FL
6 2
£303/nighttotal: £606 (2 )

Sunrise Suites Tierra Bomba Suite #403

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Key West
Bahama House - Key West, FL
9.5Excellent 464 reviews
Key West, FL
6 3
£840/nighttotal: £1680 (2 )

Bahama House

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Key West
**The Ibis & The Crane @ Old Town** Compound Near Duval + Last Key Services... - Key West, FL
9.9Excellent 481 reviews
Key West, FL
2 3
£1123/nighttotal: £5615 (5 )

**The Ibis & The Crane @ Old Town** Compound Near Duval + Last Key Services...

apartment
Key West
Bermuda Suite By Brightwild - Key West, FL
9.4Excellent 979 reviews
Key West, FL
2 1
£326/nighttotal: £1630 (5 )

Bermuda Suite By Brightwild

apartment
Key West
Sunrise Suites Saint Barts Suite #303 - Key West, FL
9.0Excellent 352 reviews
Key West, FL
4 2
£503/nighttotal: £1509 (3 )

Sunrise Suites Saint Barts Suite #303

house
Key West
Papaya Place By Avantstay Great Location W Balcony Outdoor Dining Shared Pool Hot Tub - Key West, FL
8.9Very good 134 reviews
Key West, FL
2 2
£535/nighttotal: £2675 (5 )

Papaya Place By Avantstay Great Location W Balcony Outdoor Dining Shared Pool Hot Tub

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Key West
Casa Grande By Avantstay Dt Key West Near South Beach W Pool - Key West, FL
9.8Excellent 83 reviews
Key West, FL
2 5
£1903/nighttotal: £9515 (5 )

Casa Grande By Avantstay Dt Key West Near South Beach W Pool

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Key West
Sunrise Suites Cozumel Suite #112 - Key West, FL
8.8Very good 329 reviews
Key West, FL
6 2
£326/nighttotal: £652 (2 )

Sunrise Suites Cozumel Suite #112

house
Key West

Best family friendly Key West, FL holiday rentals

Among the 2307 accommodations in Key West, FL, here are the 8 best family friendly rentals

Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool - Key West, FL
9.5Excellent 196 reviews
Key West, FL
4 2
£929/nighttotal: £2787 (3 )

Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool

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Key West
Key West Marriott Beachside Hotel - Key West, FL
8.2Very good 1342 reviews
Key West, FL
2 1
£502/nighttotal: £2008 (4 )

Key West Marriott Beachside Hotel

resort
Key West
The Bartlum By Brightwild | Luxurious Studio - Key West, FL
9.6Excellent 288 reviews
Key West, FL
4 1
£435/nighttotal: £1305 (3 )

The Bartlum By Brightwild | Luxurious Studio

apartment
Key West
Leaward Isle Island Retreat - Key West, FL
9.8Excellent 3715 reviews
Key West, FL
2 2
£541/nighttotal: £2164 (4 )

Leaward Isle Island Retreat

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Key West
Hemingways Atlantic Retreat Overlooks Smathers Beach Upgrades Galore Key West - Key West, FL
9.2Excellent 252 reviews
Key West, FL
2 2
£746/nighttotal: £2984 (4 )

Hemingways Atlantic Retreat Overlooks Smathers Beach Upgrades Galore Key West

apartment
Key West
Mar Y Sol A Spectacular Ocean Front Oasis 10 Minutes To Historic District - Key West, FL
9.1Excellent 335 reviews
Key West, FL
5 3
£865/nighttotal: £2595 (3 )

Mar Y Sol A Spectacular Ocean Front Oasis 10 Minutes To Historic District

apartment
Key West
Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 23 - Key West, FL
9.6Excellent 345 reviews
Key West, FL
2 1
£720/nighttotal: £3600 (5 )

Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 23

house
Key West
Sunrise Suites By To - Key West, FL
9.1Excellent 576 reviews
Key West, FL
6 2
£894/nighttotal: £1788 (2 )

Sunrise Suites By To

apartment
Key West

Frequently Asked Questions about vacation rentalss in Key West

  • What are the best Airbnb and holiday rentals in Key West, FL?

    Leaward Isle Island Retreat, Fontana ~ Adults Only - Pool Access Suite In Azul Mansion and Key West Villas are among the best Airbnb and holiday rentals in Key West, FL.

  • Are there any unusual vacation rentals I can find in Key West?

    Key West has some great places to stay, but if you want something unusual, you'll get plenty to choose from. You can stay in a tiny house, a sailboat, a yacht, a houseboat, or even a camper van!
  • What are the most popular Airbnbs in Key West, FL?

  • When is the best time to come to Key West?

    The months between March and May are the best time to visit Key West. Booking accommodation this time of year is going to be less pricy than in the peak winter season, but you won't miss out on the good weather.
  • What are the best holiday rentals with a pool in Key West, FL?

  • What local special dishes should I try in Key West?

    Key Lime Pie is perhaps Key West's most famous dessert, but if you want something savory, there's plenty still to chew through. Key West Pinks is a special local shrimp with a sweet taste that you can find eaten alone or accompanied with some bacon. Conch fritters are also something tasty and different to try and definitely a special in Key West.
  • What are the best rentals for families and kids in Key West, FL?

  • What's the best way to come to Key West?

    You have different options to get to Key West. You can fly, drive, or even take a boat. If you're traveling long distances, then you can fly into Key West with most major US carriers like Delta, American, USAir, United, Southwest, and Cape Air. However, if you want a scenic route, then driving to Key West over the Overseas Highway is a unique experience and worth the long drive (the route runs 113 miles long, or 170 miles long if you start from Miami). There are also buses and shuttle services available too.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Sunrise Suites Catalina Suite #311.

  • What's the must see sites in Key West?

    Visit the southernmost point of the United States before heading back to the northern side of Key West to take in the sights and performances around Mallory Square. Of course, no trip to Key West is complete without a trip to the Ernest Hemingway House!

Destinations nearby

Best pet friendly Key West, FL holiday rentals

Among the 2307 accommodations in Key West, FL, here are the 5 best pet friendly rentals

Key West Suites Hotel #201 On Duval - Key West, FL
9.6Excellent 239 reviews
Key West, FL
5 1
£476/nighttotal: £1428 (3 )

Key West Suites Hotel #201 On Duval

apartment
Key West
Duval Hideaway - Key West, FL
9.0Excellent 676 reviews
Key West, FL
6 2
£396/nighttotal: £792 (2 )

Duval Hideaway

hotel
Key West
Sunny Condo With Pool, Lovely Deck, Central Ac & Washer/dryer - Central Location - Key West, FL
9.4Excellent 224 reviews
Key West, FL
2 1
£425/nighttotal: £1700 (4 )

Sunny Condo With Pool, Lovely Deck, Central Ac & Washer/dryer - Central Location

apartment
Key West
The Curry House By Brightwild- Entire Complex - Key West, FL
8.5Very good 612 reviews
Key West, FL
3 2
£646/nighttotal: £1292 (2 )

The Curry House By Brightwild- Entire Complex

hotel
Key West
The Gardens Hotel - Key West, FL
9.6Excellent 1581 reviews
Key West, FL
2 1
£446/nighttotal: £892 (2 )

The Gardens Hotel

hotel
Key West