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Vacation Rentals & Villas in Winter Park

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2,349 villas

Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 8 minutes

Price per night from

$92

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 43 minutes

Price per night from

$115

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 8 minutes

Price per night from

$92

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

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$799

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

Winter Park house

8 bedrooms / 5 bathrooms / sleeps 20

Price per night from

$278

HOME AWAY FROM HOME in beautiful Winter Park

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$161

Winter Park, Florida Luxury Vacation Rental

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$218

Great rentals within 20 miles that match your search

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$372

Peaceful Cozy East Orlando Home (Bedroom 1)

Orlando guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$366

Beautiful 1 Bedroom Condo To Rent

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$262

LUXURY Town Center Villa Disney Studio APT

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$227

A week of dream in a resort

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$228

Marriott's Grande Vista # 1

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$365

Golf Resort and Magic of world Disney

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

Wyndham Bonnet Creek 9560 Via Encinas, Lake Buena Vista, Orlando, FL

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$425

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$327

Ocean Front Boardwalk Property

Wildwood studio

Studio / 2 bathrooms / sleeps 8

Price per night from

$523

Beautiful Large Studio Condo on the Lake

Orlando apartment

/ 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 53 minutes

Price per night from

$261

Lovely 4BR 3bth Regal Palms Townhouse

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 30 minutes

Price per night from

$148

2br - 2200ft2 - Beautiful one story 2 bed/3bath

Orlando house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$412

Marriott's Cypress Harbor Resort

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$393

3 bed/2 both Lake Front home

Lake Mary house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

Westgate Lakes Resort and SPA

Orlando condo

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$562

Orlando Timeshare For Rent

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$169

Spend a week in Orlando in a 1 bedroom villa with kitchen at Harbour Lake!

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$524

The Fountains Resort

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,015

sheraton vistana resort

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$337

2 BDRM FAMILY CONDO WEEK APRIL 17-22, 2016

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$786

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

1 bedroom / 2 bathrooms / sleeps 5

Price per night from

$721

A week in a one bed room villa

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$374

Deluxe Studio at superb Marriott's for the best price

Orlando apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 12 minutes

Price per night from

$138

House Paradise Room 1

Orlando house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$99

Price per night from

$384

Grand Villas

Orlando apartment

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$186

LUXURY Lakes Villa Disney Studio APT

Orlando villa

/ 1 bathroom / sleeps 5

Price per night from

$219

Luxurious spacious villa for rent 21 minutes to Disney

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$367

Viewing 38 of 2,349
rentals in Winter Park

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