Windsor Hills Resort holiday homes
We found 1,215 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:1 Aug - 8 Aug
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$4,848
NZ$4,848
NZ$693 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
(108 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is NZ$4,040
NZ$4,040
NZ$577 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
(115 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is NZ$4,769
NZ$4,769
NZ$681 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
(90 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
8% off
Price is NZ$4,345
NZ$4,345
NZ$621 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$2,995
NZ$2,995
NZ$428 per night
includes taxes & fees
Image gallery for 🩱Waterpark 🩳 Themed rooms 🧳 Near Walt Disney World ®️ ✨️ Private pool 💦
9.89.8 out of 10 rating
Exceptional
(32 reviews)
🩱Waterpark 🩳 Themed rooms 🧳 Near Walt Disney World ®️ ✨️ Private pool 💦
Kissimmee, FL
7% off
Price is NZ$3,095
NZ$3,095
NZ$442 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$5,157
NZ$5,157
NZ$737 per night
includes taxes & fees
Image gallery for Vibrant Frozen & Lion King Disney-Themed Home
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Vibrant Frozen & Lion King Disney-Themed Home
Kissimmee, FL
7% off
Price is NZ$6,277
NZ$6,277
NZ$897 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$4,869
NZ$4,869
NZ$696 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$5,231
NZ$5,231
NZ$747 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
8% off
Price is NZ$3,238
NZ$3,238
NZ$463 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$2,564
NZ$2,564
NZ$366 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
(101 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is NZ$3,026
NZ$3,026
NZ$432 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$6,289
NZ$6,289
NZ$898 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$5,169
NZ$5,169
NZ$738 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$2,941
NZ$2,941
NZ$420 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$6,058
NZ$6,058
NZ$865 per night
includes taxes & fees
Image gallery for *NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
9.69.6 out of 10 rating
Exceptional
(18 reviews)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Kissimmee, FL
8% off
Price is NZ$3,508
NZ$3,508
NZ$501 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$4,815
NZ$4,815
NZ$688 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
(110 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is NZ$5,265
NZ$5,265
NZ$752 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$3,242
NZ$3,242
NZ$463 per night
includes taxes & fees
Image gallery for Lake View and Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is NZ$2,183
NZ$2,183
NZ$312 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$2,559
NZ$2,559
NZ$366 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$2,147
NZ$2,147
NZ$307 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
92 reviews(92 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
115 reviews(115 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)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
63 reviews(63 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
177 reviews(177 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