Windsor Island Resort holiday homes
We found 1,057 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:19 Sept - 26 Sept
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$5,899
NZ$5,899
NZ$843 per night
includes taxes & fees
Image gallery for Villa with a pool/spa - close to Disney!
9.69.6 out of 10 rating
Exceptional
(96 reviews)
Villa with a pool/spa - close to Disney!
Davenport, FL
10% off
Price is NZ$3,572
NZ$3,572
NZ$510 per night
includes taxes & fees
Image gallery for Orlando Oasis: Exclusive Villa Close to Disney
9.29.2 out of 10 rating
Wonderful
(50 reviews)
Orlando Oasis: Exclusive Villa Close to Disney
Davenport, FL
5% off
Price is NZ$4,015
NZ$4,015
NZ$574 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
(5 reviews)
Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
Davenport, FL
13% off
Price is NZ$2,557
NZ$2,557
NZ$365 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$4,448
NZ$4,448
NZ$635 per night
includes taxes & fees
Image gallery for 7BR Resort Home BBQ Pvt Pool
8.88.8 out of 10 rating
Excellent
(5 reviews)
7BR Resort Home BBQ Pvt Pool
Davenport, FL
6% off
Price is NZ$2,637
NZ$2,637
NZ$377 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
(13 reviews)
Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
Davenport, Florida
6% off
Price is NZ$5,327
NZ$5,327
NZ$761 per night
includes taxes & fees
Image gallery for Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
Davenport, FL
13% off
Price is NZ$2,468
NZ$2,468
NZ$353 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$4,494
NZ$4,494
NZ$642 per night
includes taxes & fees
Image gallery for Elegant Home, Themed Room, Resort w/ Water Park access
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Elegant Home, Themed Room, Resort w/ Water Park access
Davenport, FL
13% off
Price is NZ$2,550
NZ$2,550
NZ$364 per night
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
14% off
Price is NZ$2,672
NZ$2,672
NZ$382 per night
includes taxes & fees
Image gallery for Themed Magical Villa in Windsor Island Resort
1010 out of 10 rating
Exceptional
(7 reviews)
Themed Magical Villa in Windsor Island Resort
Davenport, FL
6% off
Price is NZ$3,290
NZ$3,290
NZ$470 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$3,246
NZ$3,246
NZ$464 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$6,894
NZ$6,894
NZ$985 per night
includes taxes & fees
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
14% off
Price is NZ$2,740
NZ$2,740
NZ$391 per night
includes taxes & fees
Image gallery for Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
Davenport, FL
14% off
Price is NZ$2,936
NZ$2,936
NZ$419 per night
includes taxes & fees
Image gallery for 1807 Amazing 5BR Brand New House!
9.89.8 out of 10 rating
Exceptional
(22 reviews)
1807 Amazing 5BR Brand New House!
Davenport, Florida
7% off
Price is NZ$2,784
NZ$2,784
NZ$398 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$5,400
NZ$5,400
NZ$771 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$4,548
NZ$4,548
NZ$650 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$4,745
NZ$4,745
NZ$678 per night
includes taxes & fees
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Find the best place to stay - Windsor Island Resort
Showing deals for: 19 Sept - 22 Sept
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
30 reviews(30 reviews)
The current price is NZ$1,518
NZ$1,518
for 3 nights, 1 home
NZ$506 per night
includes taxes & fees
Family-Friendly 5BR Resort Home! - Pool, Perks & Sleeps 12-14
Sleeps 12 · 5 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is NZ$1,824
NZ$1,824
for 3 nights, 1 home
NZ$608 per night
includes taxes & fees
Luxury Home with Private Pool,spa, tennis court, and game room
Sleeps 14 · 6 bedrooms · 4+ bathrooms
8.08.0 out of 10
Very goodvery good
3 reviews(3 reviews)
The current price is NZ$1,892
NZ$1,892
for 3 nights, 1 home
NZ$631 per night
includes taxes & fees
Enchanted Villa - 8 Miles from Disney-pool, children's items, open layout, & W/D
Sleeps 15 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is NZ$1,735
NZ$1,735
for 3 nights, 1 home
NZ$578 per night
includes taxes & fees
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
7 reviews(7 reviews)
The current price is NZ$1,668
NZ$1,668
for 3 nights, 1 home
NZ$556 per night
includes taxes & fees
Resort retreat with private pool & lanai plus hot tub, lazy river, gym, firepit
Sleeps 12 · 5 bedrooms · 4+ bathrooms
2.02.0 out of 10
1 review(1 review)
The current price is NZ$1,485
NZ$1,485
for 3 nights, 1 home
NZ$495 per night
includes taxes & fees
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