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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Houses and Townhouses in Winter Park

Holiday homes - Holiday rentals

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
  • Apartment (180)
  • Villa (232)
  • Cottage (1)
  • House (751)
  • Townhouse (398)
  • Studio (6)
  • Condo (270)
  • Hotel apartment (19)
  • B&B (1)
  • Guest house (1)

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1,859 Holiday homes

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Great rentals within 20 miles that match your search

Kissimmee holiday home let

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
29 reviews

from £73 / night

£479 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa with shared pool, golf nearby in Davenport

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10
7 reviews

from £137 / night

£959 / week

1 / 33

Great rentals within 20 miles that match your search

Condo rental in Orlando with shared pool

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £137 / night

£822 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
6 reviews

from £64 / night

£438 - £1,825 / week

1 / 8

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

£1,141 - £2,221 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £260 / night

£1,821 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday home with indoor pool, golf nearby in ChampionsGate

ChampionsGate house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £173 / night

£1,205 / week

1 / 36

Great rentals within 20 miles that match your search

Villa rental in Orlando with shared pool

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £405 / night

£2,833 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Davenport

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £123 / night

£862 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £52 / night

£365 - £1,458 / week

1 / 4

Great rentals within 20 miles that match your search

Condo rental in Orlando with shared pool

Orlando condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £196 / night

£1,372 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday apartment with swimming pool in Davenport

Davenport apartment

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12
2 reviews

from £160 / night

£1,117 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £194 / night

£1,355 / week

1 / 37

Great rentals within 20 miles that match your search

Home rental in ChampionsGate with shared pool

ChampionsGate house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £182 / night

£1,272 / week

1 / 55

Great rentals within 20 miles that match your search

Holiday home with shared pool in Four Corners

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13
1 review

from £164 / night

£1,149 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday home with shared pool in Davenport

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
6 reviews

from £114 / night

£798 / week

1 / 64

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £75 / night

£523 / week

1 / 14

Great rentals within 20 miles that match your search

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 27

from £94 / night

£658 / week

1 / 89

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

from £133 / night

£927 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday villa rental

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £164 / night

£1,149 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £154 / night

£1,078 / week

1 / 26

Great rentals within 20 miles that match your search

Orlando holiday condo rental

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £133 / night

£925 / week

1 / 31

Great rentals within 20 miles that match your search

Home rental in Kissimmee with shared pool

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 24

from £456 / night

£3,190 / week

1 / 83

Great rentals within 20 miles that match your search

Orlando holiday apartment rental

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £187 / night

£867 / week

1 / 14

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £94 / night

£658 / week

1 / 25

Great rentals within 20 miles that match your search

Home rental in Four Corners with swimming pool

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

from £75 / night

£524 / week

1 / 80

Great rentals within 20 miles that match your search

Holiday studio in Orlando

Orlando studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £82 / night

£515 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Reunion

Reunion house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £167 / night

£1,168 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £94 / night

£658 / week

1 / 81

Great rentals within 20 miles that match your search

Home rental in Four Corners with swimming pool

Four Corners house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 20

from £114 / night

£792 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 21

from £94 / night

£657 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

from £133 / night

£927 / week

1 / 82

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 36

from £136 / night

£952 / week

1 / 100

Great rentals within 20 miles that match your search

Intercession City holiday home rental

Intercession City house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £179 / night

£1,251 / week

1 / 68

Great rentals within 20 miles that match your search

Apartment rental in Orlando with shared pool

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £126 / night

£881 / week

1 / 40

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 £75 / night

£523 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday home with shared pool in Orlando

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £169 / night

£1,181 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday home rental

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £118 / night

£1,044 / week

1 / 12

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 28

from £133 / night

£927 / week

1 / 93

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 24

from £94 / night

£658 / week

1 / 86

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