Vacation Rentals & Villas in Winter Park

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1,281 villas

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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

The Mid-Century Modern Gem

Winter Park townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$184

Stylish Boutique Guest House

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Relaxing, lake-view home near Park Avenue

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$331

Great rentals within 20 miles that match your search

Cozy, spacious, and well located 2bdr apartment!

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$102

The Best Location!!! 2-bedroom condo in Intl Area

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$102

Disney Area, stunning lake view

Kissimmee villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$309

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Price per night from

$223

Five Star Luxury 2BR-2BA Apartment Home

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$235

Lovely Villa in a central location to parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$229

Disney Dream Vacation Home

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$458

Marriott’s Grande Vista Villas

Lake Buena Vista villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$212

The Point, Studio 10 min from Universal

Orlando studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$126

1 Bedroom Villa

Celebration villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$320

Bonnet Creek - 2 Bedroom Resort Condo, 5 Mins from Disney Springs

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$285

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

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

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

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

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

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

HOME AWAY FROM HOME

Casselberry apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$143

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

Stunning 4 Bd w/ GameRoom Close to Disney 5110

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$130

Westgate Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$241

Gorgeous 2Bd Apto Close to Disney * Storey Lake ********

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$133

FUN FILLED FLORIDA HOLIDAYS 2

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$121

Storey Lake Resort Nice Pool Villa 4 miles to Disesort

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$326

Villa Westgate Lakes Resorts

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$166

Renovated condo just 2 miles from Disney with a wonderful lake views

Orlando apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$132

**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

$258

Short term vacation

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$76

STUDIO IN INTERNATIONAL DRIVE AND UNIVERSAL STUDIOS

Celebration apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$138

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

$275

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$172

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Price per night from

$286

beautiful 4 bedroom apartment

Orlando apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$338

5 Bedrooms/ 4 Bathrooms/ Storey Lake (3131 PP)

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$107

Viewing 38 of 1,281
rentals in Winter Park

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