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Vacation Rentals & Villas in Winter Park

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Price range

Per night

$10 - $500

Vacation Rentals & Villas in Winter Park

4,331 villas

Surfs Up Theme - Winter Park/Orlando

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 21 minutes

Price per night from

$75

1 / 27

Travel Themed Getaway Orlando / Winter Park

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 21 minutes

Price per night from

$75

1 / 37

Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 21 minutes

Price per night from

$80

1 / 27

The Cottage on Lake Fairview, Orlando.

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$351

1 / 35

Botanical Gardens - Orlando / Winter Park

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 21 minutes

Price per night from

$80

1 / 22

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$143

1 / 13

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

Winter Park townhouse

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$131

1 / 10

Championsgate 58 - villa with pool, game room and theater room near Disney

Winter Park house

8 bedrooms / 5 bathrooms / sleeps 18

Price per night from

$295

1 / 18

The Ritz

Winter Park house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$106

1 / 11

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 21 minutes

Price per night from

$80

1 / 20

Walkable, Peaceful, Garden District

Winter Park studio

Studio / 1 bathroom / sleeps 4

Price per night from

$87

1 / 29

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

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$596

1 / 35

Ritz’s Tiny House

Winter Park house

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$89

1 / 14
Viewing 38 of 4,331
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