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Winter Park Holiday Rentals

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19 rentals in Winter Park.
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Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!, holiday rental in Winter Park

Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Family home with flexible schedule, holiday rental in Winter Park

Family home with flexible schedule

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Just Like Home... With A Pool!, holiday rental in Winter Park

Just Like Home... With A Pool!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!, holiday rental in Winter Park

Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House, holiday rental in Winter Park

Stroll to Park Avenue from Vintage Lake-View House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Winter Park, holiday rental in Winter Park

Casa Winter Park

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Winter Park charm. Close to Park Ave, holiday rental in Winter Park

Winter Park charm. Close to Park Ave

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing location- walk to everything, holiday rental in Winter Park

Amazing location- walk to everything

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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2br - 1000ft2 - Winter Park House, holiday rental in Winter Park

2br - 1000ft2 - Winter Park House

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Winter Park-College Park-Orlando-1, holiday rental in Winter Park

Winter Park-College Park-Orlando-1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Chic Lakeside Midcentury Modern Retreat, holiday rental in Winter Park

Chic Lakeside Midcentury Modern Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Winter Park, Florida Luxury Vacation Rental, holiday rental in Winter Park

Winter Park, Florida Luxury Vacation Rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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'Lakeside' in old Winter Park (exclusive 32789zip), holiday rental in Winter Park

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Championsgate 58 - villa with pool, game room and theater room near Disney, holiday rental in Winter Park

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

8 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Winter Park

☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park-College Park-Orlando -2, holiday rental in Winter Park

Winter Park-College Park-Orlando -2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lounge on Blue Velvet Couches at a Charming Hideaway, holiday rental in Winter Park

Lounge on Blue Velvet Couches at a Charming Hideaway

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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HOME AWAY FROM HOME in beautiful Winter Park, holiday rental in Winter Park

HOME AWAY FROM HOME in beautiful Winter Park

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS, holiday rental in Winter Park

SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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