Vacation Rentals & Villas in Windsor Hills Resort

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6,234 Houses

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

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$223

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

Price per night from

$246

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$159

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$515

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$103

Windsor Hills Retreat Villa

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$458

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$159

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

Price per night from

$91

Price per night from

$194

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$203

Responds fast! avg. 2 hours 40 minutes

Price per night from

$601

Southern Dunes Golf Vacation Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Visitor” Loved it. Great neighborhood. Clean house. Easy to get a hold of people if you had questions or needed help. Walmart right around corner. Had everything you need to cook with. Great place. Defiantly will come back and recommend to anyone.

Price per night from

$117

Luxurious 2Bed/2Bath Condo Near Disney *DISCOUNTS*

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

Your VIP Home in Orlando!!!

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$212

Deluxe Studio at Disney's Saratoga at half price

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$332

Beautiful Orlando Villa "Mags Den" Calabay Parc

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 44 minutes

Price per night from

$170

The Fountains (Bluegreen)

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

Price per night from

$258

Great Furnished Resort aval in Orlando

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$229

Disney World, Universal, Orlando, Cocoa Beach

Davenport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$58

Luxury 4 Bed Villa, private pool with lake view on Lake Berkley Resort (09)

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$156

Price per night from

$196

Disney condo, 3 bdrm pool view ground floor

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$132

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$136

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Price per night from

$98

BAHAMA BAY 2 BR/2BA PLATINUM CONDO NEAR DISNEY

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$115

Disney and Orlando, 2-BR Unit-Great for Families!

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$229

Wyndham Bonnet Creek Resort ツ 2BR/2BA Deluxe Rental Condo in Orlando!

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Nice” The hotel was beautiful. However I thought it was all inclusive and it wasn't. Breakfast per person was $33 so we drove to find a Wal Mart for meals for the week. The master bathroom had a drain that was loose so someone could've fallen in and gotten hurt had I not called and had them fix it. The dryers gasket in our room was loose so the dryer door kept popping open unless you stood there to hold it closed. And the electrical outlet and my side of the bed did not work at all. House keeping is not free. And towels we're supposed to be at each pool side Cabana but they weren't. It was hard to get towels for my family of 7. Other than that the grounds were beautiful and they had lots of activities for kids.

Price per night from

$143

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

Price per night from

$114

2 BDRM FAMILY CONDO WEEK APRIL 17-22, 2016

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$687

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$194

Last week of April. The best place near Disney.

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$228

The Great Escape Lakeside, Sleeps Up to 45

Clermont villa

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 45

Price per night from

$1,294

Disney pool home in gated resort near golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

Price per night from

$189

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

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$91

Disney's Saratoga Springs Resort and Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$572

Price per night from

$171

A week in a one bed room villa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$326

Viewing 38 of 6,234
rentals in Windsor Hills Resort

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Top Destination reviews

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney
we loved this house didn't want to leave

The house was fully stocked for a large family. Loved the location. Had plenty to do on site. House was clean. We felt safe being in a gated security resort. Loved the pool and hot tub after long days at the parks. Jennifer was very helpful and responsive to all my questions before we arrived to the property. Would not hesitate to rent again. Cons on property the strollers we were going to use were broken, maybe could use some new frying pans.Some of the screens on the screened in patio was missing and the patio door the track seemed bent it was hard to close.Just those few things that were minor did not really affect our stay too much.see more
Renting condo,One mile to Disney's Animal Kingdom
Christmas Vaca

The location waa excellent just a 5 minute drive from Disney the apartment was clean and nicely decorated.There was no soap or extra toiletries so bring your own..Booking was easy..The only problem was when we arrived I was emailed the gate code and door code which were both wrong luckily the emergency number was readily available..The next day the door code was changed to something else again but we were quickly texted back with a workable code..Other than that the Stay was great!see more

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