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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$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

$258

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$401

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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$171

Ocean Front Boardwalk Property

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

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$458

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$629

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$491

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Price per night from

$343

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$151

A week of dream in a resort

Orlando house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$199

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

$196

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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$101

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

$458

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

$194

One of Disney's premier locations

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$561

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$321

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$286

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$343

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Price per night from

$257

*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. 35 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. 51 minutes

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Price per night from

$217

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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

$213

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$294

Luxurious Penthouse

Vista Cay condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$429

Westgate Resorts. 10 minutes away from Disneyworld!

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Beautiful Rental and Centrally Located” Beautiful, elegant and spacious property that is centrally located to all Orlando attractions and restaurants. Rooms were extremely spacious and comfortable to accommodate a large family with awesome amenities that include full kitchen, dining area, living room, bedrooms, pull out sofas, tv’s in every room, AC, ceiling fans, jacuzzi/soaking tubs, two fully furnished balconies with great views and so much more. Complex amenities include on-site pools, spa, activity center, discount attraction ticket sales, local transportation to area attractions, fully stocked deli/store, restaurant, arcade and mini bowling alley and more. Reasonably priced and truly a great place to consider for a memorable family vacation or couples getaway. Plenty of parking and pet friendly. You “will not” be disappointed.

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Price per night from

$355

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

$213

Vacation in Orlando, Florida

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$294

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

Viewing 38 of 767
rentals in Winter Park

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