Windsor Island Resort holiday homes
We found 1,047 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:14 Nov - 21 Nov
Image gallery for SPECIAL OFFER! Get up to 15% off Weekly Rental with complementary Pool Heating!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
SPECIAL OFFER! Get up to 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
7% off
Price is NZ$5,419
NZ$5,419
NZ$774 per night
includes taxes & fees
Image gallery for Spectacular! 9 Bedroom Disney & Universal Themed Home - Private Pool & Spa
1010 out of 10 rating
Exceptional
(7 reviews)
Spectacular! 9 Bedroom Disney & Universal Themed Home - Private Pool & Spa
Davenport, FL
7% off
Price is NZ$6,449
NZ$6,449
NZ$921 per night
includes taxes & fees
Image gallery for SPECIAL OFFER! Get UP TO 15% off Weekly Rental with complementary Pool Heating!
9.89.8 out of 10 rating
Exceptional
(37 reviews)
SPECIAL OFFER! Get UP TO 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
10% off
Price is NZ$5,078
NZ$5,078
NZ$725 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 NZ$4,516
NZ$4,516
NZ$645 per night
includes taxes & fees
Image gallery for Oasis with PVT Pool, Theme Room, Snooker with Amazing Resort
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Oasis with PVT Pool, Theme Room, Snooker with Amazing Resort
Davenport, FL
7% off
Price is NZ$4,944
NZ$4,944
NZ$706 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, FL
7% off
Price is NZ$5,237
NZ$5,237
NZ$748 per night
includes taxes & fees
Image gallery for °o° PROMO °o° Magical Villa Sleep 32+, Games, Thea
1010 out of 10 rating
Exceptional
(6 reviews)
°o° PROMO °o° Magical Villa Sleep 32+, Games, Thea
Davenport, FL
8% off
Price is NZ$21,409
NZ$21,409
NZ$3,058 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, FL
7% off
Price is NZ$4,490
NZ$4,490
NZ$641 per night
includes taxes & fees
Image gallery for Barbecue in Summer Kitchen, Smart TV by the Pool!
9.69.6 out of 10 rating
Exceptional
(55 reviews)
Barbecue in Summer Kitchen, Smart TV by the Pool!
Davenport, FL
7% off
Price is NZ$4,158
NZ$4,158
NZ$594 per night
includes taxes & fees
Image gallery for Orlando Oasis: Exclusive Villa Close to Disney
9.29.2 out of 10 rating
Wonderful
(53 reviews)
Orlando Oasis: Exclusive Villa Close to Disney
Davenport, FL
10% off
Price is NZ$4,099
NZ$4,099
NZ$586 per night
includes taxes & fees
Image gallery for Luxury Pool Home in Gated Resort!
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Luxury Pool Home in Gated Resort!
Davenport, FL
7% off
Price is NZ$4,390
NZ$4,390
NZ$627 per night
includes taxes & fees
Image gallery for Magical 5BR Villa - Game Room, Themed Rooms & Pool in Windsor Island
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Magical 5BR Villa - Game Room, Themed Rooms & Pool in Windsor Island
Davenport, FL
7% off
Price is NZ$3,548
NZ$3,548
NZ$507 per night
includes taxes & fees
Image gallery for Themed Magical Villa in Windsor Island Resort
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Themed Magical Villa in Windsor Island Resort
Davenport, FL
7% off
Price is NZ$4,064
NZ$4,064
NZ$581 per night
includes taxes & fees
Image gallery for SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
9.69.6 out of 10 rating
Exceptional
(15 reviews)
SPECIAL! Get UP TO 15% off Weekly Rental with complementary Pool & Spa Heating!
Davenport, FL
10% off
Price is NZ$5,729
NZ$5,729
NZ$818 per night
includes taxes & fees
Image gallery for Stylish 5-BR Townhouse, PVT Pool, Just Walk to the Clubhouse!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Stylish 5-BR Townhouse, PVT Pool, Just Walk to the Clubhouse!
Davenport, FL
7% off
Price is NZ$3,319
NZ$3,319
NZ$474 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
(7 reviews)
Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
Davenport, FL
7% off
Price is NZ$2,894
NZ$2,894
NZ$413 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
(8 reviews)
5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW
Davenport, FL
6% off
Price is NZ$3,326
NZ$3,326
NZ$475 per night
includes taxes & fees
Image gallery for Luxury 5BR Townhome: Private Pool & Resort Fun - 117 JW
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Luxury 5BR Townhome: Private Pool & Resort Fun - 117 JW
Davenport, FL
6% off
Price is NZ$2,483
NZ$2,483
NZ$355 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 NZ$5,279
NZ$5,279
NZ$754 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
(14 reviews)
Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
Davenport, FL
6% off
Price is NZ$5,957
NZ$5,957
NZ$851 per night
includes taxes & fees
Image gallery for Villa with a pool/spa - close to Disney!
9.69.6 out of 10 rating
Exceptional
(99 reviews)
Villa with a pool/spa - close to Disney!
Davenport, FL
12% off
Price is NZ$4,188
NZ$4,188
NZ$598 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$2,897
NZ$2,897
NZ$414 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 NZ$2,748
NZ$2,748
NZ$393 per night
includes taxes & fees
Image gallery for Adventure of a Lifetime! 5 BDR at Windsor Island
1010 out of 10 rating
Exceptional
(12 reviews)
Adventure of a Lifetime! 5 BDR at Windsor Island
Davenport, FL
7% off
Price is NZ$2,874
NZ$2,874
NZ$411 per night
includes taxes & fees
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Find the best place to stay - Windsor Island Resort
Luxury 6BR near Disney, Pool, Jacuzzi, Game & Theme Room
Sleeps 13 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Family-Friendly 5BR Resort Home! - Pool, Perks & Sleeps 12
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
AMZNG Townhome with Heated Pool - 5B 4.5B - Windsor Island Resort near Disney
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
36 reviews(36 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
10 reviews(10 reviews)
Sunny Stays | 5 bed, 4 bath | Private Pool | Sleeps 12
Sleeps 12 · 5 bedrooms · 4 bathrooms
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
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