Windsor Island Resort holiday homes
We found 989 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:31 Oct - 7 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$5,361
NZ$5,361
NZ$766 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
(36 reviews)
SPECIAL OFFER! Get UP TO 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
10% off
Price is NZ$5,112
NZ$5,112
NZ$730 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$4,470
NZ$4,470
NZ$639 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$20,478
NZ$20,478
NZ$2,925 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
(36 reviews)
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Davenport, FL
7% off
Price is NZ$4,218
NZ$4,218
NZ$603 per night
includes taxes & fees
Image gallery for Dream Residence Equipped with a Game Room, Snooker Table, PlayStation 5
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Dream Residence Equipped with a Game Room, Snooker Table, PlayStation 5
Davenport, FL
7% off
Price is NZ$4,484
NZ$4,484
NZ$641 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 NZ$4,872
NZ$4,872
NZ$696 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 NZ$4,104
NZ$4,104
NZ$586 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
6% off
Price is NZ$4,473
NZ$4,473
NZ$639 per night
includes taxes & fees
Image gallery for 7BR Resort Home BBQ Pvt Pool
9.29.2 out of 10 rating
Wonderful
(7 reviews)
7BR Resort Home BBQ Pvt Pool
Davenport, FL
13% off
Price is NZ$2,941
NZ$2,941
NZ$420 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$3,517
NZ$3,517
NZ$502 per night
includes taxes & fees
Image gallery for Newly Renovated 8BR Villa equipped with a heated pool / Spa Located near Disney
9.69.6 out of 10 rating
Exceptional
(106 reviews)
Newly Renovated 8BR Villa equipped with a heated pool / Spa Located near Disney
Davenport, FL
6% off
Price is NZ$4,596
NZ$4,596
NZ$657 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
6% off
Price is NZ$3,534
NZ$3,534
NZ$505 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$5,663
NZ$5,663
NZ$809 per night
includes taxes & fees
Image gallery for Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!
9.49.4 out of 10 rating
Exceptional
(46 reviews)
Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!
Davenport, FL
7% off
Price is NZ$6,063
NZ$6,063
NZ$866 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$2,736
NZ$2,736
NZ$391 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$2,448
NZ$2,448
NZ$350 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
11% off
Price is NZ$3,914
NZ$3,914
NZ$559 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
6% off
Price is NZ$2,545
NZ$2,545
NZ$364 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$2,722
NZ$2,722
NZ$389 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 NZ$4,169
NZ$4,169
NZ$596 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$4,154
NZ$4,154
NZ$593 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
6% off
Price is NZ$3,911
NZ$3,911
NZ$559 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor Island Resort
Family-Friendly 5BR Resort Home! - Pool, Perks & Sleeps 12
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 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)
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)
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
35 reviews(35 reviews)
Resort retreat with private pool & lanai plus hot tub, lazy river, gym, firepit
Sleeps 12 · 5 bedrooms · 4+ bathrooms
7.47.4 out of 10
Goodgood
3 reviews(3 reviews)
Resort home with private heated pool, game room, hot tub, lazy river, pool, gym
Sleeps 10 · 5 bedrooms · 5+ bathrooms
8.88.8 out of 10
Excellentexcellent
10 reviews(10 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