Vacation Rentals & Villas in Windsor Hills Resort

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6,227 Houses

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

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$224

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

$247

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$160

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$516

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

$160

Great rentals within 20 miles that match your search

Exclusive 5 bedroom townhouse at Paradise Palms

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 51 minutes

Price per night from

$184

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

Orlando Vacation Home with Private Pool & Spa

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Nice place” Our family stayed there for 9 days. We all enjoyed our stay. The house was very clean. Owner is nice to deal with, always responded quickly to my questions.

Price per night from

$172

Military owned and operated Free Heated pool and spa 8 miles to Disney

Clermont house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great House for the price.” This is a bargain house. Everything you need is already here. From strollers and bikes to all the pool toys. People have contributed along the way too which is nice to be able to leave things behind knowing they will be used. My only complaint would be that it takes about 30 minutes to get to the parks unless you know the alternative routes. Most people don't. Otherwise this place is fantastic.

Price per night from

$166

Newly remodeled Condo at Legacy Dunes with easy access - resort amenities

Kissimmee condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$131

Gibson Grove Villa

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$148

Price per night from

$146

Fireworks on the 4th if July at Disney. Mickey is waiting for you.

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$352

Reserve at Town Center Lake View Disney Villa with free Wi-Fi and Netflix

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$132

Dreamstay villa

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$126

Luxury Villa with lake view at Terra Verde Resort

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 13

Price per night from

$259

Disney Memories. Beautiful 4 Bedroom, 3 Bath,

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$172

Blue Tree Resort at Lake Buena Vista: 2-Bedrooms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 26 minutes

Price per night from

$224

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

$602

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

Price per night from

$175

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

Large Sunny Pool Home Near Disney and Golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

Price per night from

$181

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$304

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$137

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$401

Viewing 38 of 6,227
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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