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

$332

Great rentals within 20 miles that match your search

Orlando Area 4/2 Pool Disney Universal Daytona

Wekiva Springs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$223

1202 Universal Studios, International Dr

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$155

******** - Storey Lake Resort

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$119

Modern Single Home with Private Pool and Game Room (SL2807)

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$306

Storey Lake Resort 5 Bedroom Vacation Home with Pool (2019)

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$440

Great Location close to all the fun

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$326

Close to all the fun!

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$286

New Sanford Hideaway Studio Apartment + Free Parking

Sanford apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$68

Luxurious Family-Friendly 5 Bd 12 Guests w/ Screened Pool & Close to Disney

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$184

Storey Lake Resort 4 Bedroom Vacation Home with Pool (2101)

Celebration house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$343

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Price per night from

$200

Executive Suite

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$205

Brand new cozy home at Sonoma Resort at Tapestry

Kissimmee house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$399

Stunning 4Bd w/ Pool Close to Disney * Storey Lake 2881

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$174

3901OA - Sonoma Resort N

Kissimmee villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$434

3940OA - Sonoma Resort

Kissimmee villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$250

Drayton Place Staycation

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

20 Minutes to Orlando amusement

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$183

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Price per night from

$103

LUXURY 3BDRM VISTA CAY RESORT NEAR UNIVERSAL!

Orlando townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$343

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Price per night from

$172

My Orlando home

Celebration apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$179

Resort in the midst of Disney's Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$123

Private Pool in Amazing Resort Near Disney Sleeps 8

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$182

Wonderful Single-Family 4 Bd w/ Pool Close to Disney * Veranda Palms

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$166

Just 10 mins from Disney and walking distance to outlets restaurants

Celebration villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$299

3830- Sonoma Lovely Home

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$250

Lux

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 1

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Price per night from

$172

🥇 Elegant 6bd home near Disney (SL778)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$1,141

🥇 Elegant 6bd home near Disney (SL806)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,141

🥇 Premium 6bd villa close to Disney (SL782)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$1,141

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

2 Bedroom villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$343

O melhor lugar para suas férias em Família!

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$286

Viewing 38 of 1,281
rentals in Winter Park

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