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

Stylish Boutique Guest House

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

Great rentals within 20 miles that match your search

🥇 Elegant 6bd home near Disney (SL778)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$1,146

🥇 Elegant 6bd home near Disney (SL806)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,146

🥇 Premium 6bd villa close to Disney (SL782)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$1,146

Stunning 2Bd Apto Close to Disney * Storey Lake Resort 104

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$155

DOUBLE STUDIO FLAT IN INTERNATIONAL DRIVE AND UNIVERSAL STUDIOS

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$172

Casa na Disney, bem localizada e vista para o lago

Kissimmee townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$161

O melhor lugar para suas férias em Família!

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$287

Disney Deluxe Furnished 1 Bedroom Resort, Orlando

Orlando hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$308

Brand New 5-Bedroom 5-Bathroom Villa Storey Lake Resort Community

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$287

ELECTRIC HEATED PRIVATE POOL 4 BEDROOM 3 BATHROOM 2 STORY SINGLE HOUSE

Buena Ventura Lakes house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 19

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Price per night from

$343

Westgate Lakes Resorts

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$224

Tuscany Village

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Charming two themed bedrooms townhome near Disney

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 29 minutes

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Price per night from

$125

Modern Rustic Lakefront Condo at the Blue Heron Resort - just 1 mi. to Disney!

Lake Buena Vista condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$183

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

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

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

$327

Spacious 3-bed Home near Disney + Universal

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

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Price per night from

$230

Marriott Cypress Harbour Week Rental

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$245

Private Pool 5-Bed Home - Storey Lake!

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$219

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

Fabulous brand new at Storey Lake. 2bdr

Lake Buena Vista house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$170

Convenient 2Bdr Near Disney n Free Shuttle to Park

Lake Buena Vista apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$188

Lovely Villa in a central location to parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$230

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

$459

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

$190

Lovely Villa at Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$286

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

Lake Buena Vista house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Towels provided

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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

Match: Towels provided

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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

Match: Towels provided

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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

Match: Towels provided

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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

Match: Towels provided

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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

Match: Towels provided

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Price per night from

$120

Cozy and Comfy Lakeview 1BD in Central Orlando

Windermere apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Towels provided

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Price per night from

$145

Unique House w/ 5 bedrooms pool & gameroom

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 20 minutes

Match: Towels provided

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Price per night from

$264

Viewing 38 of 910
rentals in Winter Park

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