Windsor Hills Resort holiday homes
We found 1,205 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:18 Jul - 25 Jul
Image gallery for GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
1010 out of 10 rating
Exceptional
(51 reviews)
GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
Kissimmee, FL
8% off
Price is NZ$4,819
NZ$4,819
NZ$688 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
(114 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
Kissimmee, FL
7% off
Price is NZ$4,741
NZ$4,741
NZ$677 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$3,234
NZ$3,234
NZ$462 per night
includes taxes & fees
Image gallery for Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD!
1010 out of 10 rating
Exceptional
(41 reviews)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD!
Kissimmee, FL
7% off
Price is NZ$4,062
NZ$4,062
NZ$580 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$5,246
NZ$5,246
NZ$749 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$5,126
NZ$5,126
NZ$732 per night
includes taxes & fees
Image gallery for Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
6% off
Price is NZ$5,506
NZ$5,506
NZ$787 per night
includes taxes & fees
Image gallery for Mickey Star Wars Themed BR Heated Pool Free Resort Waterpark 3 miles to Disney
1010 out of 10 rating
Exceptional
(36 reviews)
Mickey Star Wars Themed BR Heated Pool Free Resort Waterpark 3 miles to Disney
Kissimmee, FL
8% off
Price is NZ$3,788
NZ$3,788
NZ$541 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$4,832
NZ$4,832
NZ$690 per night
includes taxes & fees
Image gallery for SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
1010 out of 10 rating
Exceptional
(42 reviews)
SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
Kissimmee, FL
7% off
Price is NZ$2,911
NZ$2,911
NZ$416 per night
includes taxes & fees
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(100 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
8% off
Price is NZ$3,275
NZ$3,275
NZ$468 per night
includes taxes & fees
Image gallery for Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
9.09.0 out of 10 rating
Wonderful
(42 reviews)
Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
Kissimmee, FL
8% off
Price is NZ$2,186
NZ$2,186
NZ$312 per night
includes taxes & fees
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(61 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
8% off
Price is NZ$5,417
NZ$5,417
NZ$774 per night
includes taxes & fees
Image gallery for Paradise Villa 2.5 miles from Disney Gate
1010 out of 10 rating
Exceptional
(21 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
8% off
Price is NZ$5,111
NZ$5,111
NZ$730 per night
includes taxes & fees
Image gallery for Vibrant, Poolside Condo with Encanto Magic right next to Disney!!
1010 out of 10 rating
Exceptional
(5 reviews)
Vibrant, Poolside Condo with Encanto Magic right next to Disney!!
Kissimmee, FL
7% off
Price is NZ$3,018
NZ$3,018
NZ$431 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
8% off
Price is NZ$6,494
NZ$6,494
NZ$928 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(91 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
8% off
Price is NZ$1,890
NZ$1,890
NZ$270 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
(37 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is NZ$5,929
NZ$5,929
NZ$847 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
8% off
Price is NZ$5,511
NZ$5,511
NZ$787 per night
includes taxes & fees
Image gallery for Luxury, Direct Entry Condo 2BR-2BA - Windsor Hills - Only 2 miles to Disney
8.48.4 out of 10 rating
Very good
(7 reviews)
Luxury, Direct Entry Condo 2BR-2BA - Windsor Hills - Only 2 miles to Disney
Kissimmee, FL
7% off
Price is NZ$2,143
NZ$2,143
NZ$306 per night
includes taxes & fees
Image gallery for Create Magic Moments steps away from Waterpark & Pool. On Disney's Doorstep
1010 out of 10 rating
Exceptional
(16 reviews)
Create Magic Moments steps away from Waterpark & Pool. On Disney's Doorstep
Kissimmee, FL
7% off
Price is NZ$2,734
NZ$2,734
NZ$391 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
(62 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is NZ$3,995
NZ$3,995
NZ$571 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$2,544
NZ$2,544
NZ$363 per night
includes taxes & fees
Image gallery for Create Magic Moments steps away from Waterpark & Pool. On Disney's Doorstep
1010 out of 10 rating
Exceptional
(15 reviews)
Create Magic Moments steps away from Waterpark & Pool. On Disney's Doorstep
Kissimmee, FL
7% off
Price is NZ$2,753
NZ$2,753
NZ$393 per night
includes taxes & fees
Find spaces that suit your style
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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
91 reviews(91 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
114 reviews(114 reviews)
Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
175 reviews(175 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Windsor Hills by Nova
Sleeps 12 · 6 bedrooms
6.06.0 out of 10
2 reviews(2 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)
Top rated rentals - Windsor Hills Resort
Kissimmee Stay
1010 out of 10
Exceptionalexceptional
48 reviews(48 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