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Winter Park Rentals

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Price range

Per night

$10 - $500

Winter Park Rentals

3,898 villas

Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 24 minutes

$80

1 / 27

Botanical Gardens - Orlando / Winter Park

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 24 minutes

$80

1 / 22

Surfs Up Theme - Winter Park/Orlando

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 24 minutes

$75

1 / 27

Travel Themed Getaway Orlando / Winter Park

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 24 minutes

$75

1 / 37

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

$143

1 / 13

The Cottage on Lake Fairview, Orlando.

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 6

$347

1 / 35

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 24 minutes

$80

1 / 20

"Lakeside" in old Winter Park (exclusive 32789zip)

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 8

$595

1 / 35

The Ritz

Winter Park house

3 bedrooms / 1 bathroom / sleeps 5

$105

1 / 11

Live like a Local, 2/1 in the Heart of Orlando!

Winter Park townhouse

2 bedrooms / 1 bathroom / sleeps 6

$120

1 / 10

Welcome home to Winter Park!

Winter Park guest house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 37 minutes

$90

1 / 9

Ritz’s Tiny House

Winter Park house

1 bedroom / 1 bathroom / sleeps 5

$89

1 / 14
Viewing 38 of 3,898
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