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

$114

The Mid-Century Modern Gem

Winter Park townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$183

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

$330

Great rentals within 20 miles that match your search

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$286

Bonnet Creek Resort ツ 1BR SLEEPS 4 Wyndham Orlando Condo Rental!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$91

Marriott's Cypress Harbor Resort

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Fireworks on the 4th if July at Disney. Mickey is waiting for you.

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$351

Ninovan on the Shore, A river retreat with history

Sanford house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$377

Gator Nest - Three-Bedroom Two Bath Lake View House

Oviedo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$234

Blue Tree Resort at Lake Buena Vista: 2-Bedrooms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$223

Deluxe Studio at Disney's Saratoga at half price

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$331

The Fountains (Bluegreen)

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$257

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Price per night from

$195

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$303

Disney and Orlando, 2-BR Unit-Great for Families!

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$229

Wyndham Bonnet Creek Resort ツ 2BR/2BA Deluxe Rental Condo in Orlando!

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Nice” The hotel was beautiful. However I thought it was all inclusive and it wasn't. Breakfast per person was $33 so we drove to find a Wal Mart for meals for the week. The master bathroom had a drain that was loose so someone could've fallen in and gotten hurt had I not called and had them fix it. The dryers gasket in our room was loose so the dryer door kept popping open unless you stood there to hold it closed. And the electrical outlet and my side of the bed did not work at all. House keeping is not free. And towels we're supposed to be at each pool side Cabana but they weren't. It was hard to get towels for my family of 7. Other than that the grounds were beautiful and they had lots of activities for kids.

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Price per night from

$143

2 BDRM FAMILY CONDO WEEK APRIL 17-22, 2016

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$685

Disney's Saratoga Springs Resort and Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$571

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Price per night from

$170

Wyndham Bonnet Creek Resort

Orlando hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 39 minutes

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Price per night from

$337

Ocean Front Boardwalk Property

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

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Price per night from

$457

beautiful 3 bedroom has room for all

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$310

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$628

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$490

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$343

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$151

1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$195

Wyndham Bonnet Creek Florida at Disney

Buena Ventura Lakes condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$101

Responds fast! avg. 30 minutes

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Price per night from

$113

1-bedroom / 1-bath Sleeps 4 in Orlando - 1 week

Williamsburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$99

Marriott's Sabal Palms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$457

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

Orlando house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$359

$1250+fees sleep 6, available Dec 24-Dec 31, 2022 Resort Fantasy World II

Kissimmee villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$193

Vistana Rental Lake Buena Vista FL

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$294

The Vue at Downtown Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$320

Runaway Beach Club Resort 2 Bedroom Vacation Condo (RW3101)

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$206

Viewing 38 of 1,281
rentals in Winter Park

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