Windsor Island Resort holiday rentals
We found 1,000 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 AU$4,909
AU$4,909
AU$701 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 AU$5,842
AU$5,842
AU$835 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
(38 reviews)
SPECIAL OFFER! Get UP TO 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
10% off
Price is AU$4,600
AU$4,600
AU$657 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 AU$4,091
AU$4,091
AU$584 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 AU$5,027
AU$5,027
AU$718 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 AU$4,446
AU$4,446
AU$635 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 AU$18,194
AU$18,194
AU$2,599 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 AU$4,295
AU$4,295
AU$614 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 AU$3,750
AU$3,750
AU$536 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 AU$3,713
AU$3,713
AU$530 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 AU$3,974
AU$3,974
AU$568 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 AU$3,214
AU$3,214
AU$459 per night
includes taxes & fees
Image gallery for Magical 5BR Gameroom WI Resort
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Magical 5BR Gameroom WI Resort
Davenport, FL
7% off
Price is AU$3,681
AU$3,681
AU$526 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 AU$5,190
AU$5,190
AU$741 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 AU$2,997
AU$2,997
AU$428 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 AU$2,619
AU$2,619
AU$374 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 AU$3,013
AU$3,013
AU$430 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 AU$2,247
AU$2,247
AU$321 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 AU$4,802
AU$4,802
AU$686 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 AU$2,823
AU$2,823
AU$403 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 AU$5,409
AU$5,409
AU$773 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 AU$3,794
AU$3,794
AU$542 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 AU$2,487
AU$2,487
AU$355 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 AU$2,613
AU$2,613
AU$373 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
1010 out of 10
Exceptionalexceptional
11 reviews(11 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