Windsor Hills Resort holiday rentals
We found 1,215 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:23 Jan - 30 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$3,310
S$3,310
for 7 nights, 1 villa
S$473 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$3,346
S$3,346
for 7 nights, 1 villa
S$478 per night
includes taxes & fees
Image gallery for 🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
9.89.8 out of 10, Exceptional, (181 reviews)
Exceptional
(181 reviews)
🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
Kissimmee, FL
7% off
Price is S$3,025
S$3,025
for 7 nights, 1 home
S$432 per night
includes taxes & fees
Image gallery for Our DisneyDreamVilla - minutes to DisneyWorld!!!
1010 out of 10, Exceptional, (242 reviews)
Exceptional
(242 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Kissimmee, FL
6% off
Price is S$2,622
S$2,622
for 7 nights, 1 villa
S$375 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, (180 reviews)
Exceptional
(180 reviews)
Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance
Kissimmee, FL
7% off
Price is S$2,532
S$2,532
for 7 nights, 1 apartment
S$362 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$3,044
S$3,044
for 7 nights, 1 home
S$435 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$3,078
S$3,078
for 7 nights, 1 villa
S$440 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$3,708
S$3,708
for 7 nights, 1 home
S$530 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$2,843
S$2,843
for 7 nights, 1 villa
S$406 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$3,615
S$3,615
for 7 nights, 1 home
S$516 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$3,096
S$3,096
for 7 nights, 1 home
S$442 per night
includes taxes & fees
Image gallery for FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
9.89.8 out of 10, Exceptional, (128 reviews)
Exceptional
(128 reviews)
FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is S$2,918
S$2,918
for 7 nights, 1 villa
S$417 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$3,725
S$3,725
for 7 nights, 1 home
S$532 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$3,439
S$3,439
for 7 nights, 1 home
S$491 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, (72 reviews)
Exceptional
(72 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is S$3,096
S$3,096
for 7 nights, 1 home
S$442 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$3,811
S$3,811
for 7 nights, 1 home
S$544 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$4,358
S$4,358
for 7 nights, 1 home
S$623 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$3,308
S$3,308
for 7 nights, 1 home
S$473 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$2,676
S$2,676
for 7 nights, 1 villa
S$382 per night
includes taxes & fees
Image gallery for South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
1010 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
Kissimmee, FL
7% off
Price is S$2,737
S$2,737
for 7 nights, 1 home
S$391 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is S$3,394
S$3,394
for 7 nights, 1 home
S$485 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$1,636
S$1,636
for 7 nights, 1 apartment
S$234 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$2,913
S$2,913
for 7 nights, 1 home
S$416 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$2,712
S$2,712
for 7 nights, 1 villa
S$387 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)
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)
*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)
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
243 reviews(243 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
242 reviews(242 reviews)
South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
Sleeps 12 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
64 reviews(64 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