Vacation Rentals & Villas in Windsor Hills Resort

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3,424 Houses

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Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$225

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$248

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$160

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$518

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$104

Windsor Hills Retreat Villa

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$458

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$160

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

New luxury Townhouse 1 mile from Disney

Orlando townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Florida family vacation” Loved the townhouse we rented ..would absolutely rent again from this place..it was clean and spacious and nice.

Responds fast! avg. 3 hours 7 minutes

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Price per night from

$114

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$195

Last week of April. The best place near Disney.

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

The Great Escape Lakeside, Sleeps Up to 45

Clermont villa

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 45

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Price per night from

$1,301

Luxury Condo, Steps to Disney, ESPN, Free Wi-Fi, parking, Unbeatable location

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$91

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Price per night from

$172

1 Deluxe Studio Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$133

“Great Family Memories” We give this home an A+!! Everything about it from the appearance, to the owner (Liz), to the location, and the management company combine to give you unprecedented good customer service that insures a great experience. Everything is geared towards you! The house is actually even nicer than the pictures depict!! We had 5 adults and one child stay and there was plenty of room for everyone. We loved the layout. Our granddaughter squealed with delight when she saw the Mickey Mouse room. She even asked to go to bed several nights!! We enjoyed going to nearby outlet malls, Disney, Disney Springs, restaurants close by, and even grilling out on the patio while family members swam in the pool. The game tables in the garage provided some lively competition. The greatest compliment you can give a place is to say you would return again. When we come back to this area again, Pilgrim's Paradise will be at the top of our list to stay at again! Liz made everything run smooth and was a delight to work with!! Thanks for sharing your beautiful villa with our family!!

Responds fast! avg. 2 hours 12 minutes

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Price per night from

$190

Updated Villa with Pool & Spa Near Disney!

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome” My wife and I stayed here and loved it. The house was clean and comfortable and had all the amenities needed for a vacation home that truly was a home away from home. The pool and spa were the perfect way to start and end the day after the parks and were very private with fencing and shrubs surrounding them. I've rented other homes in the area this was the best and I will definitely be coming back with the whole family. Excellent 5 stars

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$156

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$138

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$633

VACATION VILLAGE AT PARKWAY OVERVIEW

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$460

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$181

The Golden Bear

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$2,507

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$494

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Price per night from

$345

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$329

Vacation Villages at Parkway

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

Prestige 3: New Lux Home, South Fc Lake View, Pool

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$690

3 bedroom Townhouse close to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$340

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

Disney 2 Miles, Pool/Spa Home, Game Room,Themed Be

Orlando house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Perfect!” We had a wonderful experience, the house was even nicer than I expected. Bonus game room was a nice surprise. Clean, simple to find, and close to everything!

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Price per night from

$264

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$121

4 Bedroom Villa 2 Miles from Disney Entrance

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$138

8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$345

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

Beautiful 2 BR, 2BA Orlando Florida!

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$494

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

$102

Viewing 38 of 3,424
rentals in Windsor Hills Resort

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