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

Holiday homes - Holiday rentals

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 4 and above
  • 3 and above
Tripadvisor rating Vrbo rating
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 (7)
  • Villa (2)
  • House (8)
  • Townhouse (1)
  • Caravan/Mobile Home (1)

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19 Holiday homes

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Trampoline

Great rentals within 20 miles that match your search

Holiday apartment in Leesburg

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £172 / night

£1,087 - £1,216 / week

1 / 23

Great rentals within 20 miles that match your search

Leesburg holiday apartment rental

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £181 / night

£1,145 - £1,274 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday apartment in Leesburg

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £163 / night

£1,035 - £1,164 / week

1 / 24

Great rentals within 20 miles that match your search

Caravan/mobile home rental in Leesburg

Leesburg caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 10

from £134 / night

£847 - £1,623 / week

1 / 21

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 19
1 review

from £165 / night

£1,137 - £5,336 / week

1 / 65

Great rentals within 20 miles that match your search

Leesburg holiday apartment rental

Leesburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £193 / night

£1,203 - £1,461 / week

1 / 24

Great rentals within 20 miles that match your search

Reunion holiday home rental

Reunion house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 21

from £304 / night

£2,125 / week

1 / 51

Great rentals within 20 miles that match your search

Kissimmee holiday apartment rental

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £107 / night

£730 / week

1 / 30

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £328 / night

£2,295 / week

1 / 59

Great rentals within 20 miles that match your search

Clermont holiday home rental

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £213 / night

£1,487 / week

1 / 13

Great rentals within 20 miles that match your search

Kissimmee holiday apartment rental

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £348 / night

£2,352 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18
1 review

from £328 / night

£2,295 / week

1 / 62

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 £277 / night

£1,940 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Kissimmee

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14
3 reviews

from £531 / night

£3,718 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
22 reviews

from £97 / night

£679 / week

1 / 30

Great rentals within 20 miles that match your search

Home rental in Kissimmee with swimming pool, golf nearby

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
2 reviews

from £143 / night

£996 / week

1 / 25

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12
17 reviews

from £120 / night

£841 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday home in Loughman

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £68 / night

£477 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Intercession City

Intercession City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £185 / night

£1,293 / week

1 / 34

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