Windsor Hills Resort holiday homes
We found 1,211 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:15 Aug - 22 Aug
Image gallery for South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
9.89.8 out of 10 rating
Exceptional
(24 reviews)
South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
Kissimmee, FL
7% off
Price is NZ$8,838
NZ$8,838
NZ$1,263 per night
includes taxes & fees
Image gallery for Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
Kissimmee, FL
7% off
Price is NZ$5,076
NZ$5,076
NZ$725 per night
includes taxes & fees
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
9.49.4 out of 10 rating
Exceptional
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is NZ$4,852
NZ$4,852
NZ$693 per night
includes taxes & fees
Image gallery for Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
Kissimmee, FL
7% off
Price is NZ$2,867
NZ$2,867
NZ$410 per night
includes taxes & fees
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
7% off
Price is NZ$3,047
NZ$3,047
NZ$435 per night
includes taxes & fees
Image gallery for Guardians Theater 5BR Home Resort w Pool Hot Tub
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Guardians Theater 5BR Home Resort w Pool Hot Tub
Kissimmee, FL
7% off
Price is NZ$5,251
NZ$5,251
NZ$750 per night
includes taxes & fees
Image gallery for ☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
9.69.6 out of 10 rating
Exceptional
(111 reviews)
☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
Kissimmee, FL
7% off
Price is NZ$4,040
NZ$4,040
NZ$577 per night
includes taxes & fees
Image gallery for Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
8.68.6 out of 10 rating
Excellent
(37 reviews)
Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
Kissimmee, FL
6% off
Price is NZ$4,178
NZ$4,178
NZ$597 per night
includes taxes & fees
Image gallery for *Great Privacy Backyard*6BR Luxury Villa Pool/Spa
8.08.0 out of 10 rating
Very good
(18 reviews)
*Great Privacy Backyard*6BR Luxury Villa Pool/Spa
Kissimmee, FL
7% off
Price is NZ$3,857
NZ$3,857
NZ$551 per night
includes taxes & fees
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
7% off
Price is NZ$4,822
NZ$4,822
NZ$689 per night
includes taxes & fees
Image gallery for Stunning 6BR Villa with Pvt Pool, Outdoor Kitchen, and Entertainment Paradise
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Stunning 6BR Villa with Pvt Pool, Outdoor Kitchen, and Entertainment Paradise
Kissimmee, FL
6% off
Price is NZ$4,643
NZ$4,643
NZ$663 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
7% off
Price is NZ$1,937
NZ$1,937
NZ$277 per night
includes taxes & fees
Image gallery for Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
1010 out of 10 rating
Exceptional
(38 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
7% off
Price is NZ$5,312
NZ$5,312
NZ$759 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(9 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is NZ$5,206
NZ$5,206
NZ$744 per night
includes taxes & fees
Image gallery for Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
1010 out of 10 rating
Exceptional
(5 reviews)
Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
Kissimmee, FL
7% off
Price is NZ$2,565
NZ$2,565
NZ$366 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(104 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is NZ$4,476
NZ$4,476
NZ$639 per night
includes taxes & fees
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(111 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is NZ$5,361
NZ$5,361
NZ$766 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(55 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is NZ$4,083
NZ$4,083
NZ$583 per night
includes taxes & fees
Image gallery for New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
1010 out of 10 rating
Exceptional
(22 reviews)
New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
Kissimmee, FL
15% off
Price is NZ$3,297
NZ$3,297
NZ$471 per night
includes taxes & fees
Image gallery for 6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
1010 out of 10 rating
Exceptional
(85 reviews)
6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
Kissimmee, FL
7% off
Price is NZ$4,699
NZ$4,699
NZ$671 per night
includes taxes & fees
Image gallery for Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(180 reviews)
Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is NZ$2,224
NZ$2,224
NZ$318 per night
includes taxes & fees
Image gallery for 😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
9.89.8 out of 10 rating
Exceptional
(64 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is NZ$4,216
NZ$4,216
NZ$602 per night
includes taxes & fees
Image gallery for You can't get any closer to Disney!!
9.69.6 out of 10 rating
Exceptional
(57 reviews)
You can't get any closer to Disney!!
Kissimmee, FL
7% off
Price is NZ$2,606
NZ$2,606
NZ$372 per night
includes taxes & fees
Image gallery for Sunset view next to Waterpark/Pool. Moana, Beauty&Beast, etc. theme Near Disney.
1010 out of 10 rating
Exceptional
(16 reviews)
Sunset view next to Waterpark/Pool. Moana, Beauty&Beast, etc. theme Near Disney.
Kissimmee, FL
7% off
Price is NZ$2,414
NZ$2,414
NZ$345 per night
includes taxes & fees
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Find the best place to stay - Windsor Hills Resort
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
93 reviews(93 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
Windsor Hills by Nova
Sleeps 12 · 6 bedrooms
6.06.0 out of 10
2 reviews(2 reviews)
Florida Vacation Home - Tiffany's Treasure - near Disney - Kissimmee
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value