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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Condos and Houses in Crestwynd Bay

Holiday Rentals in Crestwynd Bay - Holiday Lettings - Villas

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
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  • 4 and above
  • 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
  • Apartment (6)
  • Villa (28)
  • House (43)
  • Townhouse (15)
  • Condo (46)

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138 Holiday homes

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Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £275 / night

£1,920 - £2,144 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £229 / night

£1,600 / week

1 / 31

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 13
1 review

from £192 / night

£1,344 / week

1 / 57

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16
1 review

from £367 / night

£2,382 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

from £435 / night

£3,046 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £182 / night

£1,274 / week

1 / 64

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £367 / night

£2,565 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £225 / night

£1,571 / week

1 / 20

Great rentals within 20 miles that match your search

Reunion holiday townhouse rental

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £138 / night

£960 / week

1 / 19

Great rentals within 20 miles that match your search

Apartment rental in Kissimmee

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £137 / night

£954 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
3 reviews

from £92 / night

£640 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12
2 reviews

from £197 / night

£1,740 - £1,868 / week

1 / 33

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12
4 reviews

from £344 / night

£2,405 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from £282 / night

£1,970 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £164 / night

£1,145 / week

1 / 12

Great rentals within 20 miles that match your search

Orlando holiday home rental

Orlando house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14
2 reviews

from £210 / night

£1,466 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Four Corners

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £119 / night

£828 / week

1 / 54

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £119 / night

£828 / week

1 / 65

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £110 / night

£768 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
1 review

from £138 / night

£962 / week

1 / 26

Great rentals within 20 miles that match your search

Condo accommodation in Celebration

Celebration condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £101 / night

£704 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £164 / night

£1,130 - £2,881 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 13

from £266 / night

£1,856 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £105 / night

£730 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £73 / night

£506 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £73 / night

£506 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £73 / night

£506 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £82 / night

£570 / week

1 / 29

Great rentals within 20 miles that match your search

Condo rental in Four Corners with shared pool

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £290 / night

£1,584 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday condo rental

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £302 / night

£1,619 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8
9 reviews

from £127 / night

£890 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Four Corners

Four Corners villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £166 / night

£1,161 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

from £101 / night

£704 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £92 / night

£640 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £87 / night

£608 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

from £101 / night

£704 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £83 / night

£576 / week

1 / 38

Great rentals within 20 miles that match your search

Celebration holiday villa rental

Celebration villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £96 / night

£672 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £94 / night

£653 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £69 / night

£480 / week

1 / 8

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