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Vacation Rentals & Villas in Windsor Hills Resort

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14,068 Houses

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 1 hour 17 minutes

Price per night from

$244

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

Kissimmee house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$201

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

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 12

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

$126

Pooh's Palace in Windsor Hills

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 34 minutes

Price per night from

$226

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$105

Executive Villa, Pool, Hot tub, WiFi, Games Room

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$231

Windsor Hills Retreat Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 9 minutes

Price per night from

$229

Flagstone Villa

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$264

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

Price per night from

$115

Casa Mickey, Windsor Hills Townhome

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$144

Great rentals within 20 miles that match your search

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$177

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$374

Excellent apartment in Orlando for up to 10 people

Four Corners apartment

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$354

Excellent spacious apartment in wonderful Resort

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$299

Executive Vacation Villa by Disney

Davenport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$163

Price per night from

$218

Westgate Lakes Resort & Spa Near Universal Studios Area

Orlando studio

Studio / 1 bathroom / sleeps 4

Price per night from

$195

Contemporary Villa (Alarmed) with Private Pool

Clermont villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

CONDO FOR RENT AT WESTGATE TOWN CENTER ORLANDO FLO

Kissimmee condo

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$216

Disney, Sea World, Universal, Legoland, Golf Condo

Haines City condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$89

Minions Retreat, Disney are our neighbors. Free 5g WIFI

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$118

BEAUTIFUL 2BR/2BA CONDO AT VISTA CAY RESORT

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$328

Premium Kissimmee Timeshare rental

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$376

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$368

Beautiful 1 Bedroom Condo To Rent

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$263

Two Bedroom condo in Windsor Hills close to Disney

Kissimmee apartment

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$138

A week of dream in a resort

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$229

Beautiful Vacation Home w/Lake View, Pool near Disney, SeaWorld, UniversalStudio

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$130

Marriott's Grande Vista # 1

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$367

***NEW LISTING*** Wyndham Star Island

Old Town villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 54 minutes

Price per night from

$432

4BR Family Home w/ 6 Beds + Pool - Near Disney!!

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 4 minutes

Price per night from

$189

Treetops Villa, Lake Wilson Preserve, Disney

Davenport house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$176

Apartment close to Disney parks

Kissimmee apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$209

Stunning brand new 6 bed, 4 bath, 3 living areas, games room, south facing pool

Davenport house

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$280

Amazing villa at Westgate Vacation Villas Resort

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$265

Viewing 37 of 14,068
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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