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

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

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$203

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

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's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$402

Orlando' Sunshine Resort - 2 Bedrooms, 2 Baths

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$98

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Price per night from

$171

Ocean Front Boardwalk Property

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

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Price per night from

$459

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

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

A week of dream in a resort

Orlando house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$200

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

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

One of Disney's premier locations

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$563

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$322

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

Apartment in Lake buena vista resort village & spa

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$194

WESTGATE LAKES RESORT & SPA-Orlando Florida

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 55 minutes

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Price per night from

$217

House at disney Kissimmee

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$150

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Price per night from

$164

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$171

Cypress Pointe Resort Near Downtown Disney

Orlando apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 8

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Price per night from

$214

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

Luxury 3 Bedroom Lock-Off Condo in Orlando

Orlando private room

  • 1 bedroom
  • 3 bathrooms
  • sleeps 12

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Price per night from

$214

Vacation in Orlando, Florida

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

Marriott's Cypress Harbor Resort

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

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

$353

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

$379

Viewing 38 of 859
rentals in Winter Park

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