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Villas in Key West and Holiday rentals - Holiday Lettings - Holiday Rentals Key West

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130 Holiday homes

Holiday yacht in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 6

7 Reviews

from £2,147 / night

£10,690 - £15,313 / week

Key West holiday townhouse rental

Key West townhouse

2 bedrooms • 3 bathrooms • sleeps 6

1 Reviews

from £406 / night

£2,838 / week

Holiday condo in Key West

Key West condo

2 bedrooms • 2 bathrooms • sleeps 6

4 Reviews

from £304 / night

£2,017 - £2,155 / week

Apartment rental in Key West with swimming pool

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 5

“A fun get away” Just back from a short stay in Key West with my daughters .. Really enjoyed staying here .. the condo was very clean and roomy .. and quiet .. unfortunately never made it into the pool as it closed at 8 pm and our site seeing keep us out past that time .. wished the hrs were a bit more later, like 10pm .. but we spent out time in the beautiful waters of the keys .. do not go to smathers beach, very yucky water .. about a 10-15 minute drive into town, hope to have a bit more time next time, would have liked to rent some bikes and make the ride .. the receptionist that checked us in gave us bad info that sent us walking half way around the island looking for a chili's restaurant that never existed .. but found roosters ..iguanas .. baby chicks .. and manatees on our travels .. was a nice 3 day break .. hope to go back sooner than 20 yrs

90 Reviews

from £191 / night

£1,336 - £2,984 / week

Holiday apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

“Tropical Paradise” The place was absolutely beautiful, first class accomodations. It was as nice as any island in the Carribbean with the comfort and safety of being in the United States and a whole lot closer. Hope to go back again soon.

43 Reviews

from £345 / night

£2,410 / week

Holiday apartment in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 2

2 Reviews

from £162 / night

£1,134 / week

Key West holiday home rental

Key West house

2 bedrooms • 2 bathrooms • sleeps 6

from £395 / night

£2,761 / week

Holiday yacht in Key West

Key West yacht

4 bedrooms • 2 bathrooms • sleeps 6

2 Reviews

from £235 / night

£1,641 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

14 Reviews

from £227 / night

£1,585 / week

Holiday townhouse in Key West

Key West townhouse

2 bedrooms • 1 bathroom • sleeps 6

1 Reviews

from £174 / night

£1,218 / week

Key West holiday home rental

Key West house

3 bedrooms • 3 bathrooms • sleeps 6

from £235 / night

£1,643 / week

Holiday home in Key West

Key West house

2 bedrooms • 2 bathrooms • sleeps 4

1 Reviews

from £349 / night

£2,438 / week

Holiday home in Key West

Key West house

5 bedrooms • 4 bathrooms • sleeps 12

“We had a wonderful stay” Whata great and comfortable house. I felt it was a privilege to be able to rent such a nice place. Excellent location. All in all great. The kids loved the pool and so did we.

42 Reviews

from £1,381 / night

£9,668 - £10,236 / week

Holiday townhouse in Key West

Key West townhouse

2 bedrooms • 1 bathroom • sleeps 6

5 Reviews

from £365 / night

£2,430 / week

Key West holiday townhouse rental

Key West townhouse

2 bedrooms • 2 bathrooms • sleeps 4

from £282 / night

£1,972 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms • 1 bathroom • sleeps 4

5 Reviews

from £203 / night

£1,421 - £2,639 / week

Holiday home in Key West

Key West house

2 bedrooms • 2 bathrooms • sleeps 4

from £279 / night

£1,950 / week

Key West holiday townhouse rental

Key West townhouse

3 bedrooms • 3 bathrooms • sleeps 6

9 Reviews

from £260 / night

£1,815 / week

Apartment rental in Key West with shared pool

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

2 Reviews

from £386 / night

£2,639 / week

Holiday yacht with shared pool in Key West

Key West yacht

3 bedrooms • 2 bathrooms • sleeps 7

from £893 / night

£6,246 / week

Holiday apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 4

2 Reviews

from £281 / night

£2,233 / week

Key West holiday home rental

Key West house

2 bedrooms • 2 bathrooms • sleeps 4

10 Reviews

from £460 / night

£3,219 - £4,293 / week

Key West holiday apartment rental

Key West apartment

1 bedroom • 1 bathroom • sleeps 4

9 Reviews

from £163 / night

£1,096 / week

Home rental in Key West

Key West house

3 bedrooms • 3 bathrooms • sleeps 8

from £404 / night

£2,827 / week

Condo rental in Key West with shared pool

Key West condo

1 bedroom • 1 bathroom • sleeps 4

from £155 / night

£999 / week

Condo rental in Key West

Key West condo

2 bedrooms • 1 bathroom • sleeps 4

16 Reviews

from £271 / night

£1,892 / week

Holiday townhouse in Key West

Key West townhouse

3 bedrooms • 3 bathrooms • sleeps 6

4 Reviews

from £243 / night

£1,696 / week

Holiday home rental

Key West house

1 bedroom • 1 bathroom • sleeps 4

2 Reviews

from £492 / night

£3,444 / week

Key West holiday condo rental

Key West condo

3 bedrooms • 3 bathrooms • sleeps 8

from £659 / night

£4,610 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 5

“Great place! Great Price!” The host was very helpful with everything. Good location close to Smathers beach. Everything was as described. Would stay again if ever in Key West.

38 Reviews

from £129 / night

£1,458 - £2,268 / week

Key West holiday apartment rental

Key West apartment

2 bedrooms • 3 bathrooms • sleeps 6

“Simply - Perfect” The Condo was just perfect for a family vacation. It is located in a secure gated community just outside Key west offering some peace and quiet with easy access to everything. Key west is a short drive or bike ride away. The extras are awesome, everything one would need for a carefree Key west vacation like free bikes, beach chairs, pool floats e.t.c. The owner was also very helpful recommending fun things to do in Key west. We will definitely stay here again on our next visit.

67 Reviews

from £183 / night

£1,276 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 5

“Exactly what we needed.” Owner responded in timely manner and was pleasant and answered all questions. The unit was easy to find and close to the airport. We worried about airport traffic noise interfering with sleep, but never heard them inside the condo. Condo was clean and had washer and dryer inside the unit. It was amazing to be able to do laundry when I wanted. Pool was clean, heated, and refreshing. Loved having private covered parking. It kept the car nice and cool when you got in. We'll definitely visit again in the future!

37 Reviews

from £121 / night

£1,218 - £2,030 / week

Holiday cottage in Key West

Key West cottage

1 bedroom • 1 bathroom • sleeps 2

25 Reviews

from £203 / night

£1,394 / week

Holiday apartment with shared pool in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

3 Reviews

from £488 / night

£3,410 / week

Key West holiday condo rental

Key West condo

1 bedroom • 1 bathroom • sleeps 3

from £219 / night

£1,529 / week

Holiday home in Key West

Key West house

2 bedrooms • 1 bathroom • sleeps 5

6 Reviews

from £491 / night

£3,432 / week

Key West holiday apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

1 Reviews

from £358 / night

£2,842 / week

Holiday apartment with shared pool in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

5 Reviews

from £373 / night

£2,842 - £3,126 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

1 Reviews

from £345 / night

£2,842 / week

Key West holiday apartment accommodation

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £293 / night

£2,842 / week

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Key West holidays

Located closer to Cuba than to Miami lies the island of Key West. Since its founding in the early 1800s, the island's year-round balmy, subtropical climate and unique "anything goes" flavour have made it an ideal visitor destination.

Over the years, the island has been seasoned by the rich American and Cuban culture of the 1800s, sweetened by the unabashed romantic appeal of its natural beauty, and energised by the world-renowned artistic talents of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost and Jemmy Buffett amongst others.

Residents and visitors to the island actively participate in sightseeing, touring museums, outdoor and maritime activities, and shopping by day. Later, they become part of the sunset celebration held each evening at Mallory Square, when tightrope walkers, jugglers and animal acts strive to top a more captivating performer - the fiery sun settling into the Gulf of Mexico.

The cobblestone streets of Old Town are shaded by beautiful banyan trees and lined with colourful, picturesque homes that reflect the architecture of past eras. Whether exploring these quieter streets or rocking to the vibrant beat of renowned Duval Street, visitors can savour an abundance of restaurants offering breakfast, lunch and dinner, most incorporating the Keys' fresh indigenous seafood.

Surrounding Key West are waters ranging from pastel teals to jewel-toned blues. They are home to one of the world's largest coral reefs and a bounty of shipwrecks, which make for exotic diving and snorkelling. Both novice and skilled anglers can challenge themselves to fish the Atlantic Ocean or Gulf of Mexico, targeting game fish like tarpon and marlin.

At night, the isolated island's sky is filled with stars that create a backdrop for entertainment options including jazz clubs, piano bars, drag shows and saloons. In addition, area playhouses feature Broadway-quality performances.

The tiny island has more than a dozen historic museums showing that the city's roots go deeper than picturesque palm trees and enchanting sunsets. One of the most popular is the Ernest Hemingway Home and Museum, which was the legendary author's home during the 1930s and is still home to his famous lineage of six-toed cats. The Mel Fisher Maritime Museum houses the richest single collection of 17th-century maritime and shipwreck antiquities in the Western Hemisphere, including the treasure of the Spanish galleon Nuestra Saeñora de Atocha.

Though the city is pedestrian friendly, there are two trolleys visitors can take as a method of transportation and for a tour highlighting the city's landmarks, restaurants, bars and historic sites.

Key West can be reached by flying into Miami International Airport and driving from the mainland down the magnificent Overseas Highway - featuring 42 bridges over open water and designated an All-American Road under the National Scenic Byways programme - or by ferry from points on Florida's west coast.

The island is also accessible via Key West International Airport, which is serviced by American Eagle, Delta/Express Jet, United/Silver Air, US Airways and others.

Information provided by: The Monroe County Tourist Development Council

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