Windsor Hills Resort holiday rentals
We found 1,232 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$3,296
S$3,296
for 7 nights, 1 villa
S$471 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$3,334
S$3,334
for 7 nights, 1 villa
S$476 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$2,882
S$2,882
for 7 nights, 1 villa
S$412 per night
includes taxes & fees
Image gallery for Fully Remodeled in Windsor Hills ~ 2.5 Miles to Disney World Entrance
9.89.8 out of 10, Exceptional, (179 reviews)
Exceptional
(179 reviews)
Fully Remodeled in Windsor Hills ~ 2.5 Miles to Disney World Entrance
Kissimmee, FL
7% off
Price is S$2,522
S$2,522
for 7 nights, 1 apartment
S$360 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$3,033
S$3,033
for 7 nights, 1 home
S$433 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$3,151
S$3,151
for 7 nights, 1 villa
S$450 per night
includes taxes & fees
Image gallery for 5★ Disney-Themed Villa – Renovated, Pool, Free Resort Perks – 5 Min to Disney
1010 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
5★ Disney-Themed Villa – Renovated, Pool, Free Resort Perks – 5 Min to Disney
Kissimmee, FL
8% off
Price is S$2,504
S$2,504
for 7 nights, 1 home
S$358 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$2,832
S$2,832
for 7 nights, 1 villa
S$405 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$3,602
S$3,602
for 7 nights, 1 home
S$515 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$3,085
S$3,085
for 7 nights, 1 home
S$441 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$3,711
S$3,711
for 7 nights, 1 home
S$530 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$3,752
S$3,752
for 7 nights, 1 home
S$536 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$3,085
S$3,085
for 7 nights, 1 home
S$441 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$3,767
S$3,767
for 7 nights, 1 home
S$538 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$4,341
S$4,341
for 7 nights, 1 home
S$620 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$3,295
S$3,295
for 7 nights, 1 home
S$471 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$2,860
S$2,860
for 7 nights, 1 villa
S$409 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$2,726
S$2,726
for 7 nights, 1 home
S$389 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$2,902
S$2,902
for 7 nights, 1 home
S$415 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$3,761
S$3,761
for 7 nights, 1 home
S$537 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$1,630
S$1,630
for 7 nights, 1 apartment
S$233 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$2,709
S$2,709
for 7 nights, 1 home
S$387 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$3,680
S$3,680
for 7 nights, 1 home
S$526 per night
includes taxes & fees
Image gallery for Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks
8.88.8 out of 10, Excellent, (18 reviews)
Excellent
(18 reviews)
Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks
Kissimmee, FL
7% off
Price is S$2,967
S$2,967
for 7 nights, 1 villa
S$424 per night
includes taxes & fees
Find spaces that suit your style
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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