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Holiday Lettings
> North America
> United States
> Florida
> Florida Keys
> Villas and holiday rentals in Key West

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

Price per night

£1 £750 -

Bedrooms

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • B&B (3)
  • Apartment (249)
  • Villa (75)
  • Cottage (2)
  • House (363)
  • Bungalow (1)
  • Townhouse (9)
  • Studio (22)
  • Condo (318)
  • Private room (2)
  • Hotel apartment (11)
  • Guest house (2)

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3 Holiday homes

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B&B
Jacuzzi or hot tub

Great rentals within 20 miles that match your search

Plantation holiday b&b rental

Plantation b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £138 / night

£823 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday b&b in Saint James City

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

from £685 / night

£5,486 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday b&b rental

Treasure Cay b&b

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

from £704 / night

£4,928 / week

1 / 7

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Holiday home with golf nearby in Manalapan

Manalapan house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

1 filter does not match: Property type

from £1,829 / night

£12,800 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday home in Fort Lauderdale

Fort Lauderdale house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

1 filter does not match: Property type

from £2,743 / night

£19,200 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday condo in Hollywood

Hollywood condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £128 / night

£896 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Fort Lauderdale

Fort Lauderdale condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 filter does not match: Property type

1 review

from £311 / night

£2,176 / week

1 / 28

Great rentals within 20 miles that match your search

Cape Coral holiday condo rental

Cape Coral condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £110 / night

£768 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment in Naples

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £412 / night

£2,880 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Miami

Miami apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

from £252 / night

£1,760 / week

1 / 36

Great rentals within 20 miles that match your search

Naples holiday condo rental

Naples condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £61 / night

£427 / week

1 / 19

Great rentals within 20 miles that match your search

Cape Coral holiday condo rental

Cape Coral condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £371 / night

£2,592 / week

1 / 25

Great rentals within 20 miles that match your search

Apartment rental in Hollywood

Hollywood apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £46 / night

£320 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment in Miami Beach

Miami Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

1 review

from £142 / night

£992 / week

1 / 24

Great rentals within 20 miles that match your search

Tavernier holiday home rental

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

from £64 / night

£448 / week

1 / 24

Great rentals within 20 miles that match your search

Villa rental in Cape Coral

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

5 reviews

from £168 / night

£1,175 - £1,958 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

3 reviews

from £229 / night

£1,600 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday villa in Islamorada

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £458 / night

£2,286 / week

1 / 26

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 filter does not match: Property type

7 reviews

from £822 / night

£5,754 / week

1 / 67

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Paradise Island

Paradise Island villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Property type

3 reviews

from £327 / night

£2,286 / week

1 / 7

Great rentals within 20 miles that match your search

Sunny Isles Beach holiday apartment let

Sunny Isles Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

22 reviews

from £275 / night

£1,829 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Tavernier

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Property type

from £197 / night

£1,376 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday b&b with swimming pool in Key West

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Jacuzzi or hot tub

22 reviews

from £1,038 / night

£7,267 / week

1 / 22

Great rentals within 20 miles that match your search

Hollywood holiday apartment rental

Hollywood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

12 reviews

from £119 / night

£832 / week

1 / 35

Great rentals within 20 miles that match your search

Home rental in Cudjoe Key

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 filter does not match: Property type

12 reviews

from £496 / night

£4,206 - £5,486 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday apartment in Naples

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £255 / night

£1,786 / week

1 / 35

Great rentals within 20 miles that match your search

Key West holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

17 reviews

from £389 / night

£2,652 / week

1 / 19

Great rentals within 20 miles that match your search

Naples holiday apartment rental

Naples apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

13 reviews

from £124 / night

£819 / week

1 / 9

Great rentals within 20 miles that match your search

Marco Island holiday apartment rental

Marco Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

25 reviews

from £252 / night

£1,829 - £2,720 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday apartment in Sunny Isles Beach

Sunny Isles Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 filter does not match: Property type

from £228 / night

£1,594 / week

1 / 29

Great rentals within 20 miles that match your search

Hallandale Beach holiday apartment rental

Hallandale Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £252 / night

£1,760 / week

1 / 37

Great rentals within 20 miles that match your search

Naples holiday apartment rental

Naples apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

20 reviews

from £330 / night

£2,304 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa in Cape Coral

Cape Coral villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

13 reviews

from £274 / night

£1,914 / week

1 / 46

Great rentals within 20 miles that match your search

Freeport holiday b&b rental

Freeport b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Jacuzzi or hot tub

6 reviews

from £138 / night

£960 / week

1 / 11

Great rentals within 20 miles that match your search

Sanibel Island holiday apartment rental

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

3 reviews

from £206 / night

£1,440 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday b&b in Bundi

Bundi b&b

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 3

1 filter does not match: Jacuzzi or hot tub

from £23 / night

£142 / week

1 / 39

Great rentals within 20 miles that match your search

Freeport holiday apartment rental

Freeport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £160 / night

£1,120 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday apartment in Miami Beach

Miami Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 16

1 filter does not match: Property type

2 reviews

from £365 / night

£2,554 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment accommodation

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

2 reviews

from £301 / night

£2,103 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Paradise Island

Paradise Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £458 / night

£3,200 / week

1 / 5

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