Windsor Hills Resort holiday homes
We found 1,199 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:12 Sept - 19 Sept
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$8,739
NZ$8,739
NZ$1,248 per night
includes taxes & fees
Image gallery for 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
9.89.8 out of 10 rating
Exceptional
(38 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is NZ$3,457
NZ$3,457
NZ$494 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$3,416
NZ$3,416
NZ$488 per night
includes taxes & fees
Image gallery for ☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
1010 out of 10 rating
Exceptional
(14 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
7% off
Price is NZ$4,163
NZ$4,163
NZ$595 per night
includes taxes & fees
Image gallery for Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is NZ$3,985
NZ$3,985
NZ$569 per night
includes taxes & fees
Image gallery for ✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
1010 out of 10 rating
Exceptional
(72 reviews)
✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
Kissimmee, FL
7% off
Price is NZ$2,522
NZ$2,522
NZ$360 per night
includes taxes & fees
Image gallery for Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
9.89.8 out of 10 rating
Exceptional
(91 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
9% off
Price is NZ$3,298
NZ$3,298
NZ$471 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$2,384
NZ$2,384
NZ$341 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$3,602
NZ$3,602
NZ$515 per night
includes taxes & fees
Image gallery for Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
1010 out of 10 rating
Exceptional
(36 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
7% off
Price is NZ$2,434
NZ$2,434
NZ$348 per night
includes taxes & fees
Image gallery for FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
9.69.6 out of 10 rating
Exceptional
(138 reviews)
FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
Kissimmee, FL
8% off
Price is NZ$3,318
NZ$3,318
NZ$474 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
8% off
Price is NZ$1,875
NZ$1,875
NZ$268 per night
includes taxes & fees
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10 rating
Exceptional
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is NZ$3,893
NZ$3,893
NZ$556 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
(43 reviews)
Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
Kissimmee, FL
8% off
Price is NZ$1,772
NZ$1,772
NZ$253 per night
includes taxes & fees
Image gallery for 5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
9.69.6 out of 10 rating
Exceptional
(27 reviews)
5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
Kissimmee, FL
7% off
Price is NZ$4,555
NZ$4,555
NZ$651 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$3,964
NZ$3,964
NZ$566 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
(102 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is NZ$2,156
NZ$2,156
NZ$308 per night
includes taxes & fees
Image gallery for Ultimate Adventure Villa Top Rated 5 Star Disney more
1010 out of 10 rating
Exceptional
(8 reviews)
Ultimate Adventure Villa Top Rated 5 Star Disney more
Kissimmee, Florida
8% off
Price is NZ$3,816
NZ$3,816
NZ$545 per night
includes taxes & fees
Image gallery for Dream Vacation Home at Windsor Hills Resort Homes
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Dream Vacation Home at Windsor Hills Resort Homes
Kissimmee, FL
6% off
Price is NZ$3,472
NZ$3,472
NZ$496 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$2,463
NZ$2,463
NZ$352 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
(39 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
7% off
Price is NZ$4,318
NZ$4,318
NZ$617 per night
includes taxes & fees
Image gallery for Windsor Hills Condo - Closest to the pool! - 10 minutes from Disney
9.89.8 out of 10 rating
Exceptional
(74 reviews)
Windsor Hills Condo - Closest to the pool! - 10 minutes from Disney
Kissimmee, FL
7% off
Price is NZ$1,862
NZ$1,862
NZ$266 per night
includes taxes & fees
Image gallery for Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(183 reviews)
Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is NZ$2,153
NZ$2,153
NZ$308 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
(65 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is NZ$3,572
NZ$3,572
NZ$510 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor Hills Resort
Showing deals for: 12 Sept - 15 Sept
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)
The current price is NZ$1,039
NZ$1,039
for 3 nights, 1 home
NZ$346 per night
includes taxes & fees
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)
The current price is NZ$1,870
NZ$1,870
for 3 nights, 1 villa
NZ$623 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
The current price is NZ$1,068
NZ$1,068
for 3 nights, 1 home
NZ$356 per night
includes taxes & fees
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
The current price is NZ$1,910
NZ$1,910
for 3 nights, 1 home
NZ$637 per night
includes taxes & fees
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
179 reviews(179 reviews)
The current price is NZ$1,770
NZ$1,770
for 3 nights, 1 home
NZ$590 per night
includes taxes & fees
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is NZ$1,859
NZ$1,859
for 3 nights, 1 villa
NZ$620 per night
includes taxes & fees
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