Windsor Island Resort holiday rentals
We found 1,056 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:3 Oct - 10 Oct
Image gallery for Family-Friendly 5BR Home with Pool & Clubhouse Access
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Family-Friendly 5BR Home with Pool & Clubhouse Access
Davenport, FL
14% off
Price is S$2,083
S$2,083
S$298 per night
includes taxes & fees
Image gallery for Stylish family friendly, 5 suites near Disney!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Stylish family friendly, 5 suites near Disney!
Davenport, FL
7% off
Price is S$3,390
S$3,390
S$484 per night
includes taxes & fees
Image gallery for Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
Davenport, FL
14% off
Price is S$2,207
S$2,207
S$315 per night
includes taxes & fees
Image gallery for BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
1010 out of 10 rating
Exceptional
(34 reviews)
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Davenport, FL
7% off
Price is S$3,097
S$3,097
S$442 per night
includes taxes & fees
Image gallery for Spectacular 8BR/6BA House with Ultimate Privacy, and No Rear Neighbors.
9.69.6 out of 10 rating
Exceptional
(93 reviews)
Spectacular 8BR/6BA House with Ultimate Privacy, and No Rear Neighbors.
Davenport, FL
6% off
Price is S$4,086
S$4,086
S$584 per night
includes taxes & fees
Image gallery for Themed Magical Villa in Windsor Island Resort
1010 out of 10 rating
Exceptional
(7 reviews)
Themed Magical Villa in Windsor Island Resort
Davenport, FL
6% off
Price is S$2,666
S$2,666
S$381 per night
includes taxes & fees
Image gallery for Orlando Oasis: Exclusive Villa Close to Disney
9.29.2 out of 10 rating
Wonderful
(50 reviews)
Orlando Oasis: Exclusive Villa Close to Disney
Davenport, FL
6% off
Price is S$3,415
S$3,415
S$488 per night
includes taxes & fees
Image gallery for Dazzling New 7BR Villa by Disney| Theme Rms/Pool
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Dazzling New 7BR Villa by Disney| Theme Rms/Pool
Davenport, Florida
7% off
Price is S$3,851
S$3,851
S$550 per night
includes taxes & fees
Image gallery for 1807 Amazing 5BR Brand New House!
9.89.8 out of 10 rating
Exceptional
(22 reviews)
1807 Amazing 5BR Brand New House!
Davenport, Florida
7% off
Price is S$2,224
S$2,224
S$318 per night
includes taxes & fees
Image gallery for SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
9.49.4 out of 10 rating
Exceptional
(12 reviews)
SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
Davenport, FL
7% off
Price is S$4,451
S$4,451
S$636 per night
includes taxes & fees
Image gallery for Villa with a pool/spa - close to Disney!
9.69.6 out of 10 rating
Exceptional
(96 reviews)
Villa with a pool/spa - close to Disney!
Davenport, FL
11% off
Price is S$3,390
S$3,390
S$484 per night
includes taxes & fees
Image gallery for Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
Davenport, FL
14% off
Price is S$1,960
S$1,960
S$280 per night
includes taxes & fees
Image gallery for Brand new townhouse w/private pool for up to 14 people - 5B/4.5B 5 min to Disney
1010 out of 10 rating
Exceptional
(6 reviews)
Brand new townhouse w/private pool for up to 14 people - 5B/4.5B 5 min to Disney
Davenport, FL
7% off
Price is S$2,449
S$2,449
S$350 per night
includes taxes & fees
Image gallery for 5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW
9.29.2 out of 10 rating
Wonderful
(7 reviews)
5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW
Davenport, FL
6% off
Price is S$2,299
S$2,299
S$328 per night
includes taxes & fees
Image gallery for Disney Magic Villa | 5BR with Private Pool
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Disney Magic Villa | 5BR with Private Pool
Davenport, FL
7% off
Price is S$2,258
S$2,258
S$323 per night
includes taxes & fees
Image gallery for Spacious 9BR Villa | Home Theater & Pool!
9.09.0 out of 10 rating
Wonderful
(17 reviews)
Spacious 9BR Villa | Home Theater & Pool!
Davenport, Florida
7% off
Price is S$4,456
S$4,456
S$637 per night
includes taxes & fees
Image gallery for Priv Pool, GameRm, HUGEResort!
1010 out of 10 rating
Exceptional
(5 reviews)
Priv Pool, GameRm, HUGEResort!
Davenport, FL
7% off
Price is S$3,844
S$3,844
S$549 per night
includes taxes & fees
Image gallery for Brand New 7BR Luxury Villa: Ultimate Oasis - 4446 KR
8.48.4 out of 10 rating
Very good
(5 reviews)
Brand New 7BR Luxury Villa: Ultimate Oasis - 4446 KR
Davenport, FL
6% off
Price is S$3,022
S$3,022
S$432 per night
includes taxes & fees
Image gallery for Stunning 8BR Villa | Theater/Theme Rooms/Pool
8.08.0 out of 10 rating
Very good
(6 reviews)
Stunning 8BR Villa | Theater/Theme Rooms/Pool
Davenport, Florida
7% off
Price is S$3,856
S$3,856
S$551 per night
includes taxes & fees
Image gallery for New Jungle Adventure 9BR Villa by Disney w/Pool
8.08.0 out of 10 rating
Very good
(8 reviews)
New Jungle Adventure 9BR Villa by Disney w/Pool
Davenport, Florida
7% off
Price is S$4,029
S$4,029
S$576 per night
includes taxes & fees
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Find the best place to stay - Windsor Island Resort
AMZNG Townhome with Heated Pool - 5B 4.5B - Windsor Island Resort near Disney
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
31 reviews(31 reviews)
Brand New Home w/ Private Heated Pool & BBQ Grill
Sleeps 14 · 5 bedrooms · 4+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Family-Friendly 5BR Resort Home! - Pool, Perks & Sleeps 12-14
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Just Listed! 5BR Luxury Stay @ Lazy River Resort w/ Pool — Book 7 Nights & Save!
Sleeps 11 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Resort home with private heated pool, game room, hot tub, lazy river, pool, gym
Sleeps 10 · 5 bedrooms · 5+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
8 reviews(8 reviews)
Brand new Home with 8Bed, 6Bath, Heated Private pool, SPA near Disney!
Sleeps 20 · 8 bedrooms · 6 bathrooms
9.69.6 out of 10
Exceptionalexceptional
27 reviews(27 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