Windsor Island Resort holiday rentals
We found 1,071 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:23 Jan - 30 Jan
Image gallery for °o° PROMO °o° Magical Villa Sleep 32+, Games, Thea
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
°o° PROMO °o° Magical Villa Sleep 32+, Games, Thea
Davenport, FL
8% off
Price is AU$18,306
AU$18,306
for 7 nights, 1 villa
AU$2,615 per night
includes taxes & fees
Image gallery for Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
1010 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Davenport, FL
7% off
Price is AU$3,654
AU$3,654
for 7 nights, 1 villa
AU$522 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, Exceptional, (39 reviews)
Exceptional
(39 reviews)
SPECIAL OFFER! Get UP TO 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
7% off
Price is AU$5,201
AU$5,201
for 7 nights, 1 villa
AU$743 per night
includes taxes & fees
Image gallery for Brand New Private 8BR Villa With Heated Pool + Spa Near Disney!
9.69.6 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)
Brand New Private 8BR Villa With Heated Pool + Spa Near Disney!
Davenport, FL
5% off
Price is AU$8,150
AU$8,150
for 7 nights, 1 home
AU$1,164 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, Exceptional, (52 reviews)
Exceptional
(52 reviews)
Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!
Davenport, FL
7% off
Price is AU$5,765
AU$5,765
for 7 nights, 1 villa
AU$824 per night
includes taxes & fees
Image gallery for Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
9.69.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Family Paradise w/ Game Loft, PS5, Themed Rooms & Pool – Near Disney
Davenport, FL
7% off
Price is AU$3,445
AU$3,445
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Image gallery for Spectacular 8BR/6BA House with Ultimate Privacy, and No Rear Neighbours.
9.69.6 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
Spectacular 8BR/6BA House with Ultimate Privacy, and No Rear Neighbours.
Davenport, FL
6% off
Price is AU$4,400
AU$4,400
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Image gallery for Stylish family friendly, 5 suites near Disney!
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Stylish family friendly, 5 suites near Disney!
Davenport, FL
7% off
Price is AU$4,116
AU$4,116
for 7 nights, 1 villa
AU$588 per night
includes taxes & fees
Image gallery for Spacious 9BR Villa | Home Theater & Pool!
9.09.0 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
Spacious 9BR Villa | Home Theater & Pool!
Davenport, FL
6% off
Price is AU$3,813
AU$3,813
for 7 nights, 1 villa
AU$545 per night
includes taxes & fees
Image gallery for Oasis with PVT Pool, Theme Room, Snooker with Amazing Resort
9.69.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Oasis with PVT Pool, Theme Room, Snooker with Amazing Resort
Davenport, FL
7% off
Price is AU$5,043
AU$5,043
for 7 nights, 1 home
AU$720 per night
includes taxes & fees
Image gallery for New Jungle Adventure 9BR Villa by Disney w/Pool
8.08.0 out of 10, Very good, (8 reviews)
Very good
(8 reviews)
New Jungle Adventure 9BR Villa by Disney w/Pool
Davenport, FL
6% off
Price is AU$3,712
AU$3,712
for 7 nights, 1 villa
AU$530 per night
includes taxes & fees
Image gallery for Barbecue in Summer Kitchen, Smart TV by the Pool!
9.69.6 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
Barbecue in Summer Kitchen, Smart TV by the Pool!
Davenport, FL
8% off
Price is AU$4,001
AU$4,001
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
Image gallery for Spacious 5-bedroom townhome with WiFi, fitness room in welcoming Davenport
8.48.4 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
Spacious 5-bedroom townhome with WiFi, fitness room in welcoming Davenport
Davenport, FL
7% off
Price is AU$2,953
AU$2,953
for 7 nights, 1 home
AU$422 per night
includes taxes & fees
Image gallery for NEW 9BR Windsor Island Villa Theatre/Arcade/Pool/BBQ
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
NEW 9BR Windsor Island Villa Theatre/Arcade/Pool/BBQ
Davenport, FL
7% off
Price is AU$6,725
AU$6,725
for 7 nights, 1 villa
AU$961 per night
includes taxes & fees
Image gallery for Windsor Island Water Park Oasis: 7-Bed near Disney
9.49.4 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Windsor Island Water Park Oasis: 7-Bed near Disney
Davenport, FL
7% off
Price is AU$4,348
AU$4,348
for 7 nights, 1 home
AU$621 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, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
Davenport, FL
6% off
Price is AU$5,894
AU$5,894
for 7 nights, 1 home
AU$842 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, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Magical 5BR Villa - Game Room, Themed Rooms & Pool in Windsor Island
Davenport, FL
7% off
Price is AU$3,437
AU$3,437
for 7 nights, 1 home
AU$491 per night
includes taxes & fees
Image gallery for Luxury Pool Home in Gated Resort!
9.49.4 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Luxury Pool Home in Gated Resort!
Davenport, FL
7% off
Price is AU$3,692
AU$3,692
for 7 nights, 1 home
AU$527 per night
includes taxes & fees
Image gallery for Magical 5BR Gameroom WI Resort
9.09.0 out of 10, Wonderful, (8 reviews)
Wonderful
(8 reviews)
Magical 5BR Gameroom WI Resort
Davenport, FL
6% off
Price is AU$3,405
AU$3,405
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
Image gallery for Adventure of a Lifetime! 5 BDR at Windsor Island
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Adventure of a Lifetime! 5 BDR at Windsor Island
Davenport, FL
7% off
Price is AU$2,757
AU$2,757
for 7 nights, 1 home
AU$394 per night
includes taxes & fees
Image gallery for Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
8.48.4 out of 10, Very good, (8 reviews)
Very good
(8 reviews)
Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms
Davenport, FL
6% off
Price is AU$7,286
AU$7,286
for 7 nights, 1 home
AU$1,041 per night
includes taxes & fees
Image gallery for Astonishing 7bd Dream vacation home/9mil-Disney!
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Astonishing 7bd Dream vacation home/9mil-Disney!
Davenport, FL
7% off
Price is AU$3,291
AU$3,291
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Image gallery for 4462 KR - Spacious Resort Getaway
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
4462 KR - Spacious Resort Getaway
Davenport, FL
6% off
Price is AU$3,888
AU$3,888
for 7 nights, 1 home
AU$555 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, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Stylish 5-BR Townhouse, PVT Pool, Just Walk to the Clubhouse!
Davenport, FL
7% off
Price is AU$3,221
AU$3,221
for 7 nights, 1 home
AU$460 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor Island Resort
Brand new townhouse w/private pool for up to 14 people - 5B/4.5B 5 min to Disney
Sleeps 14 · 5 bedrooms · 4+ bathrooms
1010 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
38 reviews(38 reviews)
Brand New Modern 5 Bedroom in Windsor Island! Awesome Spiderman Themed Game Room, All Bedrooms w/Private Bathrooms, Free Wifi!!
Sleeps 13 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
Relax in Style with Private Pool, BBQ and More
Sleeps 11 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Heroes and Princess Brand New 5 bedrooms with private pool at Windsor Island Resort!
Sleeps 14 · 5 bedrooms · 5 bathrooms
7.87.8 out of 10
Goodgood
6 reviews(6 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)
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