Windsor Island Resort holiday rentals
We found 1,051 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:12 Sept - 19 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 AU$5,334
AU$5,334
AU$762 per night
includes taxes & fees
Image gallery for Villa with a pool/spa - close to Disney!
9.69.6 out of 10 rating
Exceptional
(95 reviews)
Villa with a pool/spa - close to Disney!
Davenport, FL
10% off
Price is AU$3,228
AU$3,228
AU$461 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 AU$3,630
AU$3,630
AU$519 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
14% off
Price is AU$2,335
AU$2,335
AU$334 per night
includes taxes & fees
Image gallery for Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Magical 5BR Home w/ Private Pool – 200m to Clubhouse!
Davenport, FL
13% off
Price is AU$2,218
AU$2,218
AU$317 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 AU$3,520
AU$3,520
AU$503 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 AU$4,844
AU$4,844
AU$692 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 AU$2,409
AU$2,409
AU$344 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$4,065
AU$4,065
AU$581 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
14% off
Price is AU$2,300
AU$2,300
AU$329 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 AU$3,006
AU$3,006
AU$429 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$2,934
AU$2,934
AU$419 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 AU$6,234
AU$6,234
AU$891 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 AU$2,466
AU$2,466
AU$352 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 AU$2,368
AU$2,368
AU$338 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 AU$4,384
AU$4,384
AU$626 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 AU$3,655
AU$3,655
AU$522 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
Showing deals for: 12 Sept - 15 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 AU$1,372
AU$1,372
for 3 nights, 1 home
AU$457 per night
includes taxes & fees
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
6 reviews(6 reviews)
The current price is AU$1,238
AU$1,238
for 3 nights, 1 home
AU$413 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 AU$1,646
AU$1,646
for 3 nights, 1 home
AU$549 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
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is AU$1,527
AU$1,527
for 3 nights, 1 home
AU$509 per night
includes taxes & fees
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Sleeps 14 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
The current price is AU$1,888
AU$1,888
for 3 nights, 1 villa
AU$629 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 AU$1,415
AU$1,415
for 3 nights, 1 home
AU$472 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