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

The Mid-Century Modern Gem

Winter Park townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$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

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

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

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$91

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$203

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

$333

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

$259

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$197

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

$304

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

$230

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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$144

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

$689

Disney's Saratoga Springs Resort and Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$574

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$171

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

$339

Ocean Front Boardwalk Property

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

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Price per night from

$459

beautiful 3 bedroom has room for all

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$311

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$631

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$345

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

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

$197

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

$114

Responds fast! avg. 30 minutes

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Price per night from

$160

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

$459

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

Orlando house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$361

$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

$194

Vistana Rental Lake Buena Vista FL

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$295

The Vue at Downtown Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$138

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$322

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

$207

Runaway Beach Club Resort 2 Bedroom Vacation Condo (RW8103)

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$207

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$345

*CLEAN - Afforable Townhome - 5 Miles from Disney*

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Exceptional” This place was beautiful... I’ve always booked hotel rooms when I go on vacations but never again will I book a hotel... this place had everything I could ask for and more my family and I were very pleased and satisfied.

Responds fast! avg. 39 minutes

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Price per night from

$115

Viewing 38 of 1,276
rentals in Winter Park

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