Windsor Island Resort holiday rentals
We found 1,036 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:21 Nov - 28 Nov
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
8% off
Price is S$3,188
S$3,188
S$455 nightly
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$3,410
S$3,410
S$487 nightly
Includes taxes & fees
Image gallery for Spacious 5-bedroom townhome with WiFi, fitness room in welcoming Davenport
8.48.4 out of 10 rating
Very good
(5 reviews)
Spacious 5-bedroom townhome with WiFi, fitness room in welcoming Davenport
Davenport, FL
7% off
Price is S$2,446
S$2,446
S$349 nightly
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 S$6,103
S$6,103
S$872 nightly
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 S$16,020
S$16,020
S$2,289 nightly
Includes taxes & fees
Image gallery for Barbecue in Summer Kitchen, Smart TV by the Pool!
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Barbecue in Summer Kitchen, Smart TV by the Pool!
Davenport, FL
8% off
Price is S$3,944
S$3,944
S$563 nightly
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 S$4,890
S$4,890
S$699 nightly
Includes taxes & fees
Image gallery for Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
Davenport, FL
7% off
Price is S$2,836
S$2,836
S$405 nightly
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 S$4,566
S$4,566
S$652 nightly
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 S$3,367
S$3,367
S$481 nightly
Includes taxes & fees
Image gallery for 2-night or Vacation 5-Bedroom Orlando Townhouse w/ Clubhouse and Heated Pool
9.09.0 out of 10 rating
Wonderful
(28 reviews)
2-night or Vacation 5-Bedroom Orlando Townhouse w/ Clubhouse and Heated Pool
Davenport, FL
8% off
Price is S$4,428
S$4,428
S$633 nightly
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 S$3,286
S$3,286
S$469 nightly
Includes taxes & fees
Image gallery for Just Listed! 5BR Luxury Stay @ Lazy River Resort w/ Pool — Book 7 Nights & Save!
1010 out of 10 rating
Exceptional
(11 reviews)
Just Listed! 5BR Luxury Stay @ Lazy River Resort w/ Pool — Book 7 Nights & Save!
Davenport, FL
7% off
Price is S$2,436
S$2,436
S$348 nightly
Includes taxes & fees
Image gallery for Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
8.48.4 out of 10 rating
Very good
(8 reviews)
Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
Davenport, FL
6% off
Price is S$10,411
S$10,411
S$1,487 nightly
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 S$3,145
S$3,145
S$449 nightly
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
7% off
Price is S$3,426
S$3,426
S$489 nightly
Includes taxes & fees
Image gallery for Gorgeous Home w/ Pvt Pool, BBQ, PS5, Outdoor Entertainment & Water Park Access!
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Gorgeous Home w/ Pvt Pool, BBQ, PS5, Outdoor Entertainment & Water Park Access!
Davenport, FL
7% off
Price is S$2,921
S$2,921
S$417 nightly
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$2,926
S$2,926
S$418 nightly
Includes taxes & fees
Image gallery for Priv Pool, GameRm, HUGEResort!
1010 out of 10 rating
Exceptional
(5 reviews)
Priv Pool, GameRm, HUGEResort!
Davenport, FL
8% off
Price is S$5,724
S$5,724
S$818 nightly
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, FL
7% off
Price is S$4,959
S$4,959
S$708 nightly
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
22 reviews(22 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)
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
37 reviews(37 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)
Resort home with private heated pool, game room, hot tub, lazy river, pool, gym
Sleeps 10 · 5 bedrooms · 5+ bathrooms
8.68.6 out of 10
Excellentexcellent
12 reviews(12 reviews)
Sunny Stays | 5 bed, 4 bath | Private Pool | Sleeps 12
Sleeps 12 · 5 bedrooms · 4 bathrooms
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