Windsor Hills Resort holiday rentals
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 AU$7,934
AU$7,934
AU$1,133 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 AU$3,192
AU$3,192
AU$456 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 AU$3,157
AU$3,157
AU$451 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 AU$3,842
AU$3,842
AU$549 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 AU$3,675
AU$3,675
AU$525 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 AU$2,355
AU$2,355
AU$336 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 AU$3,045
AU$3,045
AU$435 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 AU$2,228
AU$2,228
AU$318 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
8% off
Price is AU$3,322
AU$3,322
AU$475 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 AU$2,255
AU$2,255
AU$322 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 AU$3,065
AU$3,065
AU$438 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 AU$1,762
AU$1,762
AU$252 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 AU$3,590
AU$3,590
AU$513 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 AU$1,707
AU$1,707
AU$244 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 AU$4,207
AU$4,207
AU$601 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
8% off
Price is AU$3,658
AU$3,658
AU$523 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 AU$2,026
AU$2,026
AU$289 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 AU$3,434
AU$3,434
AU$491 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 AU$3,208
AU$3,208
AU$458 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 AU$2,249
AU$2,249
AU$321 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 AU$3,990
AU$3,990
AU$570 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 AU$1,750
AU$1,750
AU$250 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 AU$2,023
AU$2,023
AU$289 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 AU$3,300
AU$3,300
AU$471 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
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Chalet
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)
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)
Once Upon A Dream Villa, a beautiful 6 bed / 4 bath home in Windsor Hills Resort
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.29.2 out of 10
Wonderfulwonderful
103 reviews(103 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Top rated rentals - Windsor Hills Resort
Great range of bedrooms for everyone
1010 out of 10
Exceptionalexceptional
44 reviews(44 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