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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Villas and Condos 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 (19)
  • Villa (66)
  • Cottage (1)
  • House (46)
  • Townhouse (47)
  • Condo (57)
  • Hotel apartment (8)
  • B&B (1)
  • Guest house (1)

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246 Holiday homes

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Staffed property

Great rentals within 20 miles that match your search

Orlando holiday villa rental

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8
4 reviews

from £229 / night

£1,599 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday hotel apartment in Orlando

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £242 / night

£1,695 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday home in Orlando

Orlando house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £73 / night

£512 / week

1 / 38

Great rentals within 20 miles that match your search

Orlando holiday villa rental

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
1 review

from £252 / night

£1,759 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £81 / night

£1,598 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £183 / night

£1,279 / week

1 / 6

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £179 / night

£1,247 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £216 / night

£1,507 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £87 / night

£569 - £755 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home accommodation

Davenport house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10
1 review

from £124 / night

£845 / week

1 / 67

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

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £197 / night

£1,375 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £320 / night

£2,238 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday villa rental

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £173 / night

£1,233 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday hotel apartment in Celebration

Celebration hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from £160 / night

£1,005 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £182 / night

£1,273 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday townhouse in Celebration

Celebration townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £197 / night

£1,375 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £80 / night

£618 / week

1 / 48

Great rentals within 20 miles that match your search

Condo accommodation in Kissimmee with shared pool

Kissimmee condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £54 / night

£378 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
3 reviews

from £73 / night

£505 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £160 / night

£1,119 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £274 / night

£1,918 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £137 / night

£959 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in ChampionsGate

ChampionsGate villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 13

from £245 / night

£1,694 - £4,271 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24
3 reviews

from £548 / night

£3,836 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday townhouse with golf nearby in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £130 / night

£908 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £162 / night

£1,132 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £235 / night

£1,644 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 20

from £189 / night

£1,301 - £4,738 / week

1 / 67

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 22

from £185 / night

£1,273 - £5,079 / week

1 / 87

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 6

from £183 / night

£1,279 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 22

from £181 / night

£1,245 - £5,035 / week

1 / 84

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Kissimmee

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £220 / night

£1,535 / week

1 / 53

Great rentals within 20 miles that match your search

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £137 / night

£959 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday townhouse in Celebration

Celebration townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £182 / night

£1,273 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £120 / night

£825 - £3,554 / week

1 / 65

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £149 / night

£1,021 - £3,434 / week

1 / 61

Great rentals within 20 miles that match your search

Orlando holiday apartment rental

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £274 / night

£1,644 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 24

from £189 / night

£1,301 - £4,871 / week

1 / 70

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 19

from £209 / night

£1,442 - £5,618 / week

1 / 68

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