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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Villas and condos in Windsor Hills Resort

Villas in Windsor Hills Resort and Condos - Holiday Lettings - Holiday Rentals Windsor Hills Resort

Price per night

£1 £750 -

Bedrooms

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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 (27)
  • Apartment (21)
  • Cottage (4)
  • House (44)
  • Barn (1)
  • Townhouse (4)
  • Studio (4)
  • Condo (7)
  • Private room (1)
  • B&B (1)
  • Log cabin (1)

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27 Holiday homes

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Villa
Smokers

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Davenport

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £124 / night

£1,145 - £2,229 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Orlando

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £156 / night

£1,089 / week

1 / 8

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £236 / night

£1,517 - £1,677 / week

1 / 25

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £236 / night

£1,517 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa in Clermont

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
1 review

from £236 / night

£1,517 - £1,677 / week

1 / 37

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £248 / night

£1,597 - £1,757 / week

1 / 41

Great rentals within 20 miles that match your search

Villa rental in Clermont with swimming pool

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £200 / night

£1,278 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa rental

Clermont villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £200 / night

£1,278 - £1,438 / week

1 / 38

Great rentals within 20 miles that match your search

Mount Dora holiday villa rental

Mount Dora villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £260 / night

£1,677 - £1,837 / week

1 / 37

Great rentals within 20 miles that match your search

Clermont holiday villa let

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £236 / night

£1,517 / week

1 / 27

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £200 / night

£1,278 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Clermont

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

from £188 / night

£1,198 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Clermont

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £228 / night

£1,358 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Clermont

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £248 / night

£1,597 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa in Clermont

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £224 / night

£1,438 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6
8 reviews

from £146 / night

£1,020 - £3,439 / week

1 / 10

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
1 review

from £248 / night

£1,597 / week

1 / 30

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8
2 reviews

from £260 / night

£1,677 / week

1 / 28

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £250 / night

£174,034 / week

1 / 20

Great rentals within 20 miles that match your search

Orlando holiday villa rental

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £159 / night

£915 - £1,287 / week

1 / 6

Great rentals within 20 miles that match your search

Villa rental in Clermont with swimming pool

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
2 reviews

from £212 / night

£1,358 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday villa in Clearwater

Clearwater villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
2 reviews

from £365 / night

£1,920 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Clermont

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10
1 review

from £248 / night

£1,597 / week

1 / 27

Great rentals within 20 miles that match your search

Villa rental in Orlando with shared pool

Orlando villa

  • 1 bathroom
  • sleeps 5

from £153 / night

£916 - £1,474 / week

1 / 13

Great rentals within 20 miles that match your search

Villa accommodation in Orlando with shared pool

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £229 / night

£1,603 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Clermont

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
1 review

from £200 / night

£1,278 / week

1 / 28

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
38 reviews

from £115 / night

£802 - £888 / week

1 / 18

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Orlando holiday villa rental

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Smokers

4 reviews

from £229 / night

£1,603 / week

1 / 16

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: Smokers

29 reviews

from £94 / night

£654 / week

1 / 37

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: Smokers

15 reviews

from £138 / night

£962 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Smokers

from £157 / night

£1,100 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Smokers

1 review

from £106 / night

£738 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday villa letting

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Smokers

from £321 / night

£2,245 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Smokers

1 review

from £115 / night

£802 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Clermont

Clermont villa

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 45

1 filter does not match: Smokers

from £1,036 / night

£7,252 / week

1 / 55

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Orlando

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Smokers

from £458 / night

£3,664 / week

1 / 4

Great rentals within 20 miles that match your search

Villa rental in Orlando with shared pool

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Smokers

from £137 / night

£956 / week

1 / 10

Great rentals within 20 miles that match your search

Villa rental in Orlando

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Smokers

from £261 / night

£1,828 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Smokers

from £106 / night

£738 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday studio rental

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £367 / night

£2,565 / week

1 / 19

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