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

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241 Holiday homes

Holiday yacht in Key West

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 6

7

from £2,024 / night

£12,190 - £14,825 / week

Key West holiday townhouse rental

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

1

from £457 / night

£4,572 / week

Holiday condo in Key West

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

4

Responds fast! avg. 1 hour 56 minutes

from £210 / night

£1,377 - £2,294 / 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

88

from £197 / night

£1,373 - £2,650 / week

Key West holiday condo rental

Key West condo

1 bedroom / 1 bathroom / sleeps 4

from £172 / night

£1,202 / week

Home rental in Key West

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

3

from £802 / night

£5,613 / 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.

42

Responds fast! avg. 2 hours 29 minutes

from £343 / night

£2,172 / week

Holiday apartment in Key West

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

1

from £189 / night

£1,318 / week

Key West holiday home rental

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

from £395 / night

£2,761 / week

Holiday home with swimming pool in Key West

Key West house

2 bedrooms / 1 bathroom / sleeps 4

1

from £156 / night

£1,090 / week

Holiday apartment with shared pool in Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

from £156 / night

£1,090 / week

Holiday apartment in Key West

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

from £215 / night

£1,500 / week

Holiday home rental

Key West house

1 bedroom / 2 bathrooms / sleeps 2

2

from £153 / night

£1,068 / week

Holiday home with swimming pool in Key West

Key West house

5 bedrooms / 5 bathrooms / sleeps 10

5

from £559 / night

£3,913 / week

Holiday home with shared pool in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

27

from £228 / night

£1,593 / week

Holiday apartment with shared pool in Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

1

from £128 / night

£895 / week

Holiday yacht in Key West

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

2

from £235 / night

£1,641 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

14

Responds fast! avg. 2 hours 1 minutes

from £255 / night

£1,781 / week

Boathouse rental in Key West

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

4

Responds fast! avg. 3 hours 1 minutes

from £182 / night

£1,271 / week

Holiday apartment with shared pool in Key West

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

from £134 / night

£934 / week

Key West holiday cottage rental

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

from £155 / night

£1,079 / week

Holiday townhouse in Key West

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

1

from £197 / night

£1,375 / week

Key West holiday home rental

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect Location!!!” This condo was clean comfortable and located minutes from all the action on Duval and in Mallory Square. The location was perfect combination of peace and quiet at home while only block away from all the excitement of the surrounding area. Was a little disappointed with the size of the pool on admirals lane but other than that it was a wonderful trip and would stay in the same location again. People at at Home Key West were very efficient and congenial. Thank You!!

32

from £200 / night

£1,398 / week

Key West holiday home rental

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

from £259 / night

£1,811 / week

Holiday home in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 3 hours 35 minutes

from £403 / night

£2,819 / 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.

41

from £1,003 / night

£7,018 / week

Holiday townhouse in Key West

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

4

Responds fast! avg. 3 hours 21 minutes

from £288 / night

£2,017 - £3,483 / week

Holiday home with shared pool in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect location!!” We stayed for a week in December and had the time of our lives. Duval Breeze exceeded our high expectations. Our rooftop community was above cool restaurants. Next to a CVS and right on the cooler, quieter end of Duval. Cool pool upstairs where you can lay out and read. I'd highly recommend this place. We had 3 permanent residents and one couch crasher. We rented bicycles for the week and didn't need a car. I jogged out the front door and by 8am was sipping a chai latte on a bench on Duval. Great time. Perfect location. Will stay again.

57

from £192 / night

£1,342 / week

Holiday apartment with shared pool in Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

4

from £148 / night

£1,034 / week

Key West holiday townhouse rental

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

from £323 / night

£2,259 / week

Holiday apartment in Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

5

from £211 / night

£1,475 - £2,535 / week

Home rental in Key West with swimming pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

from £356 / night

£2,488 / week

Key West holiday home accommodation

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

1

from £238 / night

£1,660 / week

Key West holiday apartment rental

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £245 / night

£1,716 / week

Key West holiday home rental

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

from £231 / night

£1,616 / week

Holiday home in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

from £279 / night

£1,950 / week

Holiday yacht rental

Key West yacht

3 bedrooms / 1 bathroom / sleeps 6

3

from £319 / night

£1,780 - £2,419 / week

Key West holiday townhouse rental

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

9

Responds fast! avg. 36 minutes

from £293 / night

£2,048 / week

Holiday home with swimming pool in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“A peaceful, beautiful tropical retreat home” This is a beautiful place for a tropical retreat. It is a short bike ride to anywhere on the island (rent bikes 2 blocks away), yet refreshingly away from the noise of Duval. The home itself is beautifully decorated and comfortable. I found the master suite bed a little hard for my personal liking, but it was clean and welcoming. There were a few electrical problems with the home -- the lights burn out quickly and the lights above the sink in the master bath did not work during our stay, but it didn't matter much because there is a beautiful sky light just above. I know they were planning to have some electrical work done after our stay, so this is likely not going to be a problem for future occupants. There is not much storage in the "one butt" kitchen, but it didn't bother us much during our stay. The pool is nice and was well maintained while we were there. The pool gets some sun, but is mostly shaded by large, beautiful trees, so the water is continuously a refreshing temperature -- doesn't get too hot like a lot of the pools in the summer in the Keys. We had folks over for dinner while we were there and found that the serving dishes, cooking utensils, etc., were sufficient and even nice looking for entertaining purposes. Groundskeepers keep the lush tropical foilage beautiful while you are there, and they are in and out quickly, so you may likely never know they are there. One small issue is that the home seemed a bit musty at times, so definitely use the fans when showering and keep the air conditioning on while away. Also, the large room with the dining table is not air conditioned, and it is a little too warm out there in the summer to dine comfortably -- there are great ceiling fans in that room, however, and we spent most mornings having coffee in this room. Overall, it's a nice place and I'd stay there again.

11

from £222 / night

£1,554 / week

Holiday home with shared pool in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay!” The only problem was that there were a lot of small ants everywhere. If anything was left on the kitchen counter or on the floor, they would be all over. Great location! I love staying in Truman annex, a little bit quieter and off the beaten path but yet so easy to walk anywhere.

35

from £164 / night

£1,146 / week

Viewing 40 of 241
rentals in Key West

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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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