Windsor Hills Resort holiday rentals
We found 1,230 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:16 Jan - 23 Jan
Image gallery for Mickey's Pool House- Minutes away from Disney World
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Mickey's Pool House- Minutes away from Disney World
Kissimmee, FL
8% off
Price is S$3,283
S$3,283
for 7 nights, 1 villa
S$469 per night
includes taxes & fees
Image gallery for Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills
9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills
Kissimmee, FL
7% off
Price is S$3,320
S$3,320
for 7 nights, 1 villa
S$474 per night
includes taxes & fees
Image gallery for 6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
9.89.8 out of 10, Exceptional, (128 reviews)
Exceptional
(128 reviews)
6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
Kissimmee, FL
7% off
Price is S$2,870
S$2,870
for 7 nights, 1 villa
S$410 per night
includes taxes & fees
Image gallery for Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance
9.89.8 out of 10, Exceptional, (179 reviews)
Exceptional
(179 reviews)
Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance
Kissimmee, FL
7% off
Price is S$2,512
S$2,512
for 7 nights, 1 apartment
S$359 per night
includes taxes & fees
Image gallery for Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is S$3,021
S$3,021
for 7 nights, 1 home
S$432 per night
includes taxes & fees
Image gallery for 5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
9.89.8 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
Kissimmee, FL
6% off
Price is S$3,082
S$3,082
for 7 nights, 1 villa
S$440 per night
includes taxes & fees
Image gallery for 5★ Disney-Themed Villa – Pool, Free Resort Perks, Renovated – 5 Min to Disney
1010 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
5★ Disney-Themed Villa – Pool, Free Resort Perks, Renovated – 5 Min to Disney
Kissimmee, FL
8% off
Price is S$2,426
S$2,426
for 7 nights, 1 home
S$347 per night
includes taxes & fees
Image gallery for South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
9.29.2 out of 10, Wonderful, (24 reviews)
Wonderful
(24 reviews)
South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
Kissimmee, FL
7% off
Price is S$2,820
S$2,820
for 7 nights, 1 villa
S$403 per night
includes taxes & fees
Image gallery for AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms
9.89.8 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms
Kissimmee, FL
8% off
Price is S$3,587
S$3,587
for 7 nights, 1 home
S$512 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,072
S$3,072
for 7 nights, 1 home
S$439 per night
includes taxes & fees
Image gallery for 6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
9.89.8 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
8% off
Price is S$3,696
S$3,696
for 7 nights, 1 home
S$528 per night
includes taxes & fees
Image gallery for Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
9.49.4 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
Kissimmee, FL
7% off
Price is S$3,687
S$3,687
for 7 nights, 1 home
S$527 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, Exceptional, (71 reviews)
Exceptional
(71 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is S$3,072
S$3,072
for 7 nights, 1 home
S$439 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, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is S$3,824
S$3,824
for 7 nights, 1 home
S$546 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, Exceptional, (85 reviews)
Exceptional
(85 reviews)
6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
Kissimmee, FL
8% off
Price is S$3,987
S$3,987
for 7 nights, 1 home
S$570 per night
includes taxes & fees
Image gallery for 5-star family home with water park, private pool/hot tub- 2 stoplights to Disney
9.89.8 out of 10, Exceptional, (112 reviews)
Exceptional
(112 reviews)
5-star family home with water park, private pool/hot tub- 2 stoplights to Disney
Kissimmee, FL
8% off
Price is S$3,281
S$3,281
for 7 nights, 1 home
S$469 per night
includes taxes & fees
Image gallery for GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
Kissimmee, FL
8% off
Price is S$4,322
S$4,322
for 7 nights, 1 home
S$617 per night
includes taxes & fees
Image gallery for Luxury 5BR Villa Near Disney w/ Pool & Game Room
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Luxury 5BR Villa Near Disney w/ Pool & Game Room
Kissimmee, FL
8% off
Price is S$2,863
S$2,863
for 7 nights, 1 villa
S$409 per night
includes taxes & fees
Image gallery for Windsor Hills - close to Disney, free heated pool, newly renovated bathroom
8.88.8 out of 10, Excellent, (84 reviews)
Excellent
(84 reviews)
Windsor Hills - close to Disney, free heated pool, newly renovated bathroom
Kissimmee, FL
8% off
Price is S$2,890
S$2,890
for 7 nights, 1 home
S$413 per night
includes taxes & fees
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is S$2,715
S$2,715
for 7 nights, 1 home
S$388 per night
includes taxes & fees
Image gallery for Getaway with Mickey in Windsor Hills!
9.89.8 out of 10, Exceptional, (147 reviews)
Exceptional
(147 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee, FL
7% off
Price is S$1,624
S$1,624
for 7 nights, 1 apartment
S$232 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, Wonderful, (9 reviews)
Wonderful
(9 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
7% off
Price is S$3,716
S$3,716
for 7 nights, 1 home
S$531 per night
includes taxes & fees
Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
1010 out of 10, Exceptional, (220 reviews)
Exceptional
(220 reviews)
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
Kissimmee, FL
7% off
Price is S$2,698
S$2,698
for 7 nights, 1 home
S$385 per night
includes taxes & fees
Image gallery for Disney's Doorstep Villa at Windsor Hills
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Disney's Doorstep Villa at Windsor Hills
Kissimmee, FL
7% off
Price is S$3,656
S$3,656
for 7 nights, 1 home
S$522 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills Resort
FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
128 reviews(128 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
20 reviews(20 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
242 reviews(242 reviews)
Relaxing 6BDR Villa just 15 mins from Disney w/ a Private Pool & Clubhouse!
Sleeps 12 · 6 bedrooms · 3+ bathrooms
6.06.0 out of 10
1 review(1 review)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
97 reviews(97 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