Vacation Rentals & Villas in Winter Park

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2br - 1000ft2 - Winter Park House

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$115

Great rentals within 20 miles that match your search

COMFORTABLE HOME IN A PRIVILEGED AREA , JUST 7 MI TO DISNEY PARKS!

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$189

Lovely Villa at Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$285

Gorgeous 4 Bd Close to Disney * 5156 Compass Bay Resort

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$133

Amazing 4 Bd Close to Disney * 5162C Compass Bay Resort

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$123

Stunning 4 Bd Close to Disney * 5146 Compass Bay

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$119

Family Friendly 4 Bd Close to Disney * 5158 Compass Bay Resort

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$133

Breathtaking 4 Bd Close to Disney * 5160 Compass Bay Resort

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$133

Marvelous 4 Bd Close to Disney * 5166 Compass Bay

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$133

Cozy and Comfy Lakeview 1BD in Central Orlando

Windermere apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$144

Villa Westgate Lakes Resorts

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$166

Charming and Cozy Condo next to the Convention Center and Sea World

Celebration apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$274

Charming and Cozy Condo next to the Convention Center and Sea World

Celebration apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$286

**New**Modern**By Universal, Volcano Bay, ICON Park & Disney**With King Bed

Celebration apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$257

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Price per night from

$256

20% OFF |Sweet Spot Villa |3BR (1 En-Suite) | Pool and Gym Onsite

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$229

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Price per night from

$400

20% OFF | Hidden Gem |3BR (1 En-Suite) | Resort Amenities

Orlando townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$194

Disney Vista Luxury Villa 5 beds/5.5 baths

Orlando house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$216

2 Apartamentos de lujo en Westgate Town Center a pocas millas de Disney

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$503

SunnyDay

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 16 minutes

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Price per night from

$132

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Price per night from

$685

Lake View Charmer l Private Pool l Pets l Disney

Buena Ventura Lakes house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$229

Family friendly! Close to MCO, Disney, Universal

Orlando house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$520

Apartamento Westgate Lakes

Orlando apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$327

The tranquil charm with king bed mins to Speed World

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 27 minutes

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Price per night from

$136

Sunny Orlando Vacation

Longwood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$229

Best Disney Resort Condo Orlando Florida

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$164

Westgate Leisure Resort 2br suite, Sunday check-in

Lake Buena Vista condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$86

Crystal in Storylake resort 5beds w/pool, gameroom

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$264

4bd Cozy Green Oasis/Pool/ClosetoDisney (Sleeps 6)

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$196

Tranquil Sunset Escape~Pool~Hot Tub~Resort Access

Kissimmee house

  • 13 bedrooms
  • 10 bathrooms
  • sleeps 26

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Price per night from

$406

3brdrm home near WinterPark and Downtown Orlando

Eatonville house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$178

Stylish and cozy apt/ sleeps 7 people/near all attractions

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$206

Unique House w/ 5 bedrooms pool & gameroom

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$264

Responds fast! avg. 3 hours 19 minutes

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Price per night from

$136

Lake Buena Vista Suite 2 Queens

Orlando hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$189

Sheraton Vistana Resort 1br suite, Sunday check-in

Lake Buena Vista condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$102

Viewing 38 of 768
rentals in Winter Park

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