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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

Property rating (out of 5)
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  • 3 and above
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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
  • Villa (2)
  • House (6)
  • Camper van (1)
  • Condo (4)
  • Guest house (1)

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14 Holiday homes

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Great rentals within 20 miles that match your search

Tampa ski camper van to rent.

Tampa camper van

  • 1 bedroom
  • 2 bathrooms
  • sleeps 8

from £87 / night

£610 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £321 / night

£2,245 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday condo rental

Port Saint Lucie condo

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12
1 review

from £889 / night

£6,220 / week

1 / 181

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from £133 / night

£928 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £81 / night

£564 / week

1 / 44

Great rentals within 20 miles that match your search

Home rental in Davenport

Davenport house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £90 / night

£628 / week

1 / 38

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £128 / night

£892 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

from £457 / night

£3,200 / week

1 / 117

Great rentals within 20 miles that match your search

Holiday condo in New Smyrna Beach

New Smyrna Beach condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £302 / night

£2,112 / week

1 / 59

Great rentals within 20 miles that match your search

Reunion holiday home rental

Reunion house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 21

from £302 / night

£2,112 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday home in Clermont

Clermont house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10
1 review

from £202 / night

£1,411 / week

1 / 6

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

from £458 / night

£3,206 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home with indoor pool, golf nearby in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £275 / night

£1,924 / week

1 / 32

Great rentals within 20 miles that match your search

Madeira Beach ski guest house to rent.

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
1 review

from £138 / night

£962 / week

1 / 100

Great rentals within 20 miles that match your search

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Marco Island holiday home rental

Marco Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Mountain Views

from £161 / night

£1,122 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Mountain Views

2 reviews

from £147 / night

£916 - £1,466 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Mountain Views

3 reviews

from £73 / night

£507 / week

1 / 33

Great rentals within 20 miles that match your search

Home rental in Davenport

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Mountain Views

from £155 / night

£1,007 / week

1 / 28

Great rentals within 20 miles that match your search

Home rental in Orlando with swimming pool

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Mountain Views

2 reviews

from £163 / night

£1,135 / week

1 / 68

Great rentals within 20 miles that match your search

Orlando holiday villa rental

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Mountain Views

29 reviews

from £94 / night

£654 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Mountain Views

5 reviews

from £170 / night

£1,187 / week

1 / 48

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

15 reviews

from £138 / night

£962 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment rental

Plantation apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Mountain Views

1 review

from £106 / night

£738 / week

1 / 11

Great rentals within 20 miles that match your search

St. Petersburg holiday home rental

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

from £206 / night

£1,443 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday apartment rental

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Mountain Views

2 reviews

from £54 / night

£358 - £541 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Orlando

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

15 reviews

from £206 / night

£1,649 - £2,016 / week

1 / 14

Great rentals within 20 miles that match your search

Marco Island holiday villa rental

Marco Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

from £419 / night

£2,931 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday villa in Cape Coral

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Mountain Views

3 reviews

from £116 / night

£806 / week

1 / 32

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Mountain Views

from £183 / night

£1,282 / week

1 / 26

Great rentals within 20 miles that match your search

Marco Island holiday condo rental

Marco Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Mountain Views

from £206 / night

£1,443 / week

1 / 27

Great rentals within 20 miles that match your search

Townhouse rental in Key Largo with swimming pool

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

8 reviews

from £321 / night

£1,512 - £3,206 / week

1 / 17

Great rentals within 20 miles that match your search

Apartment accommodation in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Mountain Views

7 reviews

from £321 / night

£1,329 - £2,748 / week

1 / 16

Great rentals within 20 miles that match your search

Sarasota holiday apartment rental

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Mountain Views

from £236 / night

£1,649 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday bungalow in Port Charlotte

Port Charlotte bungalow

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Mountain Views

from £87 / night

£602 - £1,303 / week

1 / 22

Great rentals within 20 miles that match your search

Englewood holiday townhouse rental

Englewood townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

2 reviews

from £161 / night

£1,122 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday condo in Anna Maria Island

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Mountain Views

10 reviews

from £167 / night

£1,168 / week

1 / 68

Great rentals within 20 miles that match your search

Home rental in Orlando with swimming pool, golf nearby

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

1 filter does not match: Mountain Views

2 reviews

from £145 / night

£1,026 - £1,732 / week

1 / 31

Great rentals within 20 miles that match your search

Cape Coral holiday home rental

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Mountain Views

14 reviews

from £88 / night

£614 - £979 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday hotel apartment in Orlando

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Mountain Views

from £243 / night

£1,700 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo in Reunion

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Mountain Views

from £109 / night

£763 / week

1 / 9

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