Vacation Rentals & Villas in Winter Park

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121 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

Great rentals within 20 miles that match your search

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Price per night from

$171

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

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

Responds fast! avg. 30 minutes

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$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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$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

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$322

Westgate Lakes, Orlando Florida - 4 Bedroom Villa - Huge Resort with everything

Orlando hotel apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

“Worth It!!!” Our family stayed at Westgate Lakes for one week during Spring Break. We had a four bedroom condo and the space was fabulous!!! We were more than impressed with the resort staff and all the ammenities. The location was also very excellent and so easy to find and so close to the attractions we wanted to visited. The resort was very clean in all areas and very safe and secure for our family.

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$409

Lakefront Townhouse 5 Star LOCATION

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lakefront Townhouse Review” Centrally located to everything. Place very clean and well kept.Enjoyed our stay there and would recommend the place to anyone. The agent was very helpful and polite. We are going back in 2011.

Responds fast! avg. 36 minutes

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Price per night from

$109

Elegant Modern Condo/Apt. in Sunny Orlando !

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic Vacation in Orlando” Thanks to Jan we probably had the best vacation in years. The condo is very well situated. It’s only a five minute drive from restaurants and supermarkets, such as Aldi and WalMart. For us it was very important since we have two kids and love to taste local food and cook in. The kitchen is equipped with high class appliances and well stocked with everything you need for cooking. Needless to say, the condo is kept impeccably clean and spotless. We were also impressed by the overall design of the condo and the furniture. Having two bathrooms was an additional plus. The master bathroom with its expensive marble counter top and tiled with natural stone, seemed to have come out from an upscale designer office. The pool located only a few steps away from our porch was a little jewel. It was never crowded and on most times we had it only to ourselves. The gated community is located in a well-kept prestigious area and its admin personnel helped us a lot in planning our visits to the amusement park, printing tickets, etc. Jan is a very friendly person, going out of his way to make our stay at the condo enjoyable. His professionalism in running the condo and his attention to detail is fantastic. The condo definitely exceeded all my expectations. We’d love to return to Jan’s place once again and probably enjoy a longer stay there. Alexander & Natalya D., Yekaterinburg, Russia

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Price per night from

$88

Bargain Vacation Home near Disney

Kissimmee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$121

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Price per night from

$257

1 week Westgate Resort Studio in Orlando_Sleeps 4

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$107

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

Studio with an amazing terrace

International Drive hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$109

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Price per night from

$165

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

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

Luxurious Penthouse

Vista Cay condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$431

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

Marriott's Cypress Harbor Resort

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$402

Disney location vila with 4 poster bed, pool, wifi

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$158

The best place to Orlando

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$184

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Price per night from

$262

Orlando Lake 5* Location Disney Universal Convention #175

Orlando townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 36 minutes

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Price per night from

$109

Weekly 2 bedroom Apartment for 8 guest all amenities included

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 17 minutes

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Price per night from

$121

COZY HOME CLOSE TO LOOP & PET FRIENDLY

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

sheraton vistana resort

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

Luxurious Waterfront Studio

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$144

Saratoga Springs Resort and Spa 1 bedroom 714 sq ft deluxe Villa with King Bed

Buena Ventura Lakes villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

Westgate Lakes 2 bedroom villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$165

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rentals in Winter Park

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