Windsor Island Resort holiday homes
We found 1,062 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:15 Aug - 22 Aug
Image gallery for BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
1010 out of 10 rating
Exceptional
(33 reviews)
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Davenport, FL
7% off
Price is NZ$3,704
NZ$3,704
NZ$529 per night
includes taxes & fees
Image gallery for SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
1010 out of 10 rating
Exceptional
(10 reviews)
SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
Davenport, FL
7% off
Price is NZ$6,275
NZ$6,275
NZ$896 per night
includes taxes & fees
Image gallery for Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
8.08.0 out of 10 rating
Very good
(5 reviews)
Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
Davenport, Florida
6% off
Price is NZ$7,309
NZ$7,309
NZ$1,044 per night
includes taxes & fees
Image gallery for Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
1010 out of 10 rating
Exceptional
(12 reviews)
Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
Davenport, Florida
6% off
Price is NZ$7,052
NZ$7,052
NZ$1,007 per night
includes taxes & fees
Image gallery for Windsor Island Themed Theater, Pool, Avatar
1010 out of 10 rating
Exceptional
(5 reviews)
Windsor Island Themed Theater, Pool, Avatar
Davenport, FL
7% off
Price is NZ$3,340
NZ$3,340
NZ$477 per night
includes taxes & fees
Image gallery for Stylish home, Themed Room with Private Pool
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Stylish home, Themed Room with Private Pool
Davenport, FL
6% off
Price is NZ$2,965
NZ$2,965
NZ$424 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 NZ$5,301
NZ$5,301
NZ$757 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 NZ$3,356
NZ$3,356
NZ$479 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
(5 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 NZ$3,307
NZ$3,307
NZ$472 per night
includes taxes & fees
Image gallery for Discover Your Perfect Getaway | 8BR Wonder
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Discover Your Perfect Getaway | 8BR Wonder
Davenport, Florida
7% off
Price is NZ$5,418
NZ$5,418
NZ$774 per night
includes taxes & fees
Image gallery for 5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW
9.49.4 out of 10 rating
Exceptional
(6 reviews)
5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW
Davenport, FL
6% off
Price is NZ$3,691
NZ$3,691
NZ$527 per night
includes taxes & fees
Image gallery for Escape to a Themed Bedroom Retreat with PS5, Private Pool & BBQ
1010 out of 10 rating
Exceptional
(31 reviews)
Escape to a Themed Bedroom Retreat with PS5, Private Pool & BBQ
Davenport, FL
6% off
Price is NZ$3,036
NZ$3,036
NZ$434 per night
includes taxes & fees
Image gallery for Great home with Water Park, Comfort & Themed Rooms
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Great home with Water Park, Comfort & Themed Rooms
Davenport, FL
6% off
Price is NZ$3,348
NZ$3,348
NZ$478 per night
includes taxes & fees
Image gallery for Luxury 10 bedroom MANSION on ideal XL corner lot in Windsor Island Resort
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Luxury 10 bedroom MANSION on ideal XL corner lot in Windsor Island Resort
Davenport, FL
7% off
Price is NZ$7,024
NZ$7,024
NZ$1,003 per night
includes taxes & fees
Image gallery for Dazzling Windsor Island 7BR Villa/Themed gameroom
1010 out of 10 rating
Exceptional
(41 reviews)
Dazzling Windsor Island 7BR Villa/Themed gameroom
Davenport, FL
7% off
Price is NZ$4,369
NZ$4,369
NZ$624 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 NZ$5,686
NZ$5,686
NZ$812 per night
includes taxes & fees
Image gallery for Spacious 9BR Villa | Home Theater & Pool!
8.88.8 out of 10 rating
Excellent
(16 reviews)
Spacious 9BR Villa | Home Theater & Pool!
Davenport, Florida
7% off
Price is NZ$6,342
NZ$6,342
NZ$906 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 NZ$5,552
NZ$5,552
NZ$793 per night
includes taxes & fees
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Find the best place to stay - Windsor Island Resort
Brand New Home w/ Private Heated Pool & BBQ Grill
Sleeps 14 · 5 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
15 reviews(15 reviews)
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
28 reviews(28 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
6 reviews(6 reviews)
Windsor Island - Cozy Pool Townhouse near to Disney
Sleeps 12 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Resort home with private heated pool, game room, hot tub, lazy river, pool, gym
Sleeps 10 · 5 bedrooms · 5+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14
Sleeps 14 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 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