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Best Vacation Rentals in Winter Park - Holiday Lettings - Cabins

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102 Vacation rentals

Vacation townhouse in Winter Park

Winter Park townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $184 / night

$1,283 / week

1 / 17

Vacation home rental

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $331 / night

$2,317 / week

1 / 14

Home rental in Winter Park

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $229 / night

$1,603 / week

1 / 27

Vacation home in Winter Park

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $115 / night

$802 / week

1 / 13

Vacation home in Winter Park

Winter Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from $352 / night

$2,464 / week

1 / 13

Vacation home in Winter Park

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $101 / night

$707 / week

1 / 9

Winter Park Vacation home rental

Winter Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $320 / night

$2,240 / week

1 / 30

Vacation home in Winter Park

Winter Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $122 / night

$854 / week

1 / 30

Ski home to rent in Winter Park

Winter Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $130 / night

$910 / week

1 / 16

Vacation apartment in Winter Park

Winter Park apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $150 / night

$1,050 / week

1 / 30

Vacation home rental

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $119 / night

$833 / week

1 / 20

Winter Park ski cottage to rent.

Winter Park cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $226 / night

$1,582 / week

1 / 29

Vacation home in Winter Park

Winter Park house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $60 / night

$420 / week

1 / 8

Vacation home in Winter Park

Winter Park house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $272 / night

$1,904 / week

1 / 30

Winter Park ski condo to rent.

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $356 / night

$2,492 / week

1 / 28

Vacation home rental

Winter Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $243 / night

$1,701 / week

1 / 30

Vacation apartment in Winter Park

Winter Park apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $140 / night

$980 / week

1 / 12

Winter Park Vacation apartment rental

Winter Park apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $140 / night

$980 / week

1 / 12

Winter Park Vacation home rental

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $154 / night

$1,078 / week

1 / 11

Home rental in Winter Park

Winter Park house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $171 / night

$1,197 / week

1 / 22

Ski home to rent in Winter Park

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $186 / night

$1,302 / week

1 / 23

Vacation home in Winter Park

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $160 / night

$1,120 / week

1 / 17

Ski cottage to rent in Winter Park

Winter Park cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $120 / night

$840 / week

1 / 14

Vacation home rental

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $196 / night

$1,372 / week

1 / 16

Vacation home in Winter Park

Winter Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $228 / night

$1,596 / week

1 / 17

Studio rental in Winter Park

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 6

from $119 / night

$833 / week

1 / 19

Winter Park Vacation home rental

Winter Park house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $77 / night

$539 / week

1 / 13

Winter Park Vacation home rental

Winter Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,204 / week

1 / 30

Winter Park Vacation home rental

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $197 / night

$1,379 / week

1 / 14

Vacation home in Winter Park

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $90 / night

$630 / week

1 / 16

Winter Park Vacation apartment rental

Winter Park apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $176 / night

$1,232 / week

1 / 17

Winter Park Vacation apartment rental

Winter Park apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $190 / night

$1,330 / week

1 / 8

Apartment rental in Winter Park

Winter Park apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $189 / night

$1,323 / week

1 / 30

Vacation condo accommodation

Winter Park condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $116 / night

$812 / week

1 / 14

Vacation apartment in Winter Park

Winter Park apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $120 / night

$840 / week

1 / 27

Vacation home in Winter Park

Winter Park house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $93 / night

$651 / week

1 / 12

Winter Park Vacation home rental

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $130 / night

$910 / week

1 / 30

Winter Park Vacation apartment rental

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $95 / night

$665 / week

1 / 13

Vacation home rental

Winter Park house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $101 / night

$707 / week

1 / 30

Vacation home in Winter Park

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $161 / night

$1,127 / week

1 / 11