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Vacation Rentals & Villas in Winter Park

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2,695 villas

Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 25 minutes

Price per night from

$92

The Cottage on Lake Fairview, Orlando.

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

Price per night from

$590

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$120

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 25 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

$801

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

$266

Winter Park, Florida Luxury Vacation Rental

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$220

Great rentals within 20 miles that match your search

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$176

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$373

Westgate Lakes Resort & Spa Near Universal Studios Area

Orlando studio

Studio / 1 bathroom / sleeps 4

Price per night from

$195

Peaceful Cozy East Orlando Home (Bedroom 1)

Orlando guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

BEAUTIFUL 2BR/2BA CONDO AT VISTA CAY RESORT

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$170

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$328

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$367

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 great little apartment in College Park, Orlando.

Orlando apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 49 minutes

Price per night from

$147

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

$366

Golf Resort and Magic of world Disney

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

Paul's Place at Ventura

Ventura apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$117

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

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$426

2br - 1100ft2 - FLORIDA VACATION

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$159

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$328

Beautiful Garage Apartment Just North Of Downtown

Orlando apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$151

5* Sheraton Vistana Resort, 2BR/2BA, close to Disney/Universal, many amenities

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$209

Bedroom for Renting . 1 - 3 can sleep

Orlando house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$105

Ocean Front Boardwalk Property

Wildwood studio

Studio / 2 bathrooms / sleeps 8

Price per night from

$524

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

$149

Oviedo Charmer

Goldenrod house

3 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$184

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

Orlando house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$412

A great loft apartment in College Park, Orlando.

Orlando apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 49 minutes

Price per night from

$147

Marriott's Cypress Harbor Resort

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$394

3 bed/2 both Lake Front home

Lake Mary house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

Westgate Lakes Resort and SPA

Orlando condo

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$563

2 BD 2 BA Bonnet Creek In Gates of Disney World FL

Celebration villa

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$348

VH2 | STOREY LAKE - TOWNHOME, WITH PRIVATE POOL 4B/3B

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$217

Viewing 38 of 2,695
rentals in Winter Park

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