Windsor Island Resort holiday rentals
We found 1,076 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Island Resort
Showing deals for:30 Jan - 6 Feb
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$17,903
AU$17,903
for 7 nights, 1 villa
AU$2,558 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$5,059
AU$5,059
for 7 nights, 1 villa
AU$723 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, (64 reviews)
Exceptional
(64 reviews)
Brand New Private 8BR Villa With Heated Pool + Spa Near Disney!
Davenport, FL
5% off
Price is AU$7,849
AU$7,849
for 7 nights, 1 home
AU$1,121 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$5,607
AU$5,607
for 7 nights, 1 villa
AU$801 per night
includes taxes & fees
Image gallery for SPECIAL OFFER! Get up to 15% off Weekly Rental with complementary Pool Heating!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
SPECIAL OFFER! Get up to 15% off Weekly Rental with complementary Pool Heating!
Davenport, FL
7% off
Price is AU$4,804
AU$4,804
for 7 nights, 1 villa
AU$686 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$3,425
AU$3,425
for 7 nights, 1 home
AU$489 per night
includes taxes & fees
Image gallery for Family-Friendly 5BR Home with Pool & Clubhouse Access
9.29.2 out of 10, Wonderful, (5 reviews)
Wonderful
(5 reviews)
Family-Friendly 5BR Home with Pool & Clubhouse Access
Davenport, FL
7% off
Price is AU$3,249
AU$3,249
for 7 nights, 1 home
AU$464 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$4,005
AU$4,005
for 7 nights, 1 villa
AU$572 per night
includes taxes & fees
Image gallery for FREE Waterpark & clubhouse! 7 BR-Windsor Island Resort!
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
FREE Waterpark & clubhouse! 7 BR-Windsor Island Resort!
Davenport, FL
7% off
Price is AU$3,824
AU$3,824
for 7 nights, 1 home
AU$546 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$4,922
AU$4,922
for 7 nights, 1 home
AU$703 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$4,042
AU$4,042
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Image gallery for Stunning 8BR Villa | Theater/Theme Rooms/Pool
8.08.0 out of 10, Very good, (6 reviews)
Very good
(6 reviews)
Stunning 8BR Villa | Theater/Theme Rooms/Pool
Davenport, FL
7% off
Price is AU$3,794
AU$3,794
for 7 nights, 1 villa
AU$542 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
7% off
Price is AU$4,045
AU$4,045
for 7 nights, 1 villa
AU$578 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$2,902
AU$2,902
for 7 nights, 1 home
AU$415 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$6,864
AU$6,864
for 7 nights, 1 villa
AU$981 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$4,221
AU$4,221
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
Image gallery for Ultimate Family Fun: Spacious 5-Bedroom Home with Private Pool & NBA Game Room!
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Ultimate Family Fun: Spacious 5-Bedroom Home with Private Pool & NBA Game Room!
Davenport, FL
7% off
Price is AU$3,748
AU$3,748
for 7 nights, 1 home
AU$535 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$5,857
AU$5,857
for 7 nights, 1 home
AU$837 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$3,425
AU$3,425
for 7 nights, 1 home
AU$489 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$4,049
AU$4,049
for 7 nights, 1 home
AU$578 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, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Luxury 10 bedroom MANSION on ideal XL corner lot in Windsor Island Resort
Davenport, FL
7% off
Price is AU$6,719
AU$6,719
for 7 nights, 1 home
AU$960 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$7,067
AU$7,067
for 7 nights, 1 home
AU$1,010 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$3,287
AU$3,287
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$3,782
AU$3,782
for 7 nights, 1 home
AU$540 per night
includes taxes & fees
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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)
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)
Relax in Style with Private Pool, BBQ and More
Sleeps 11 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Disney Fireworks By The Pool! 18 guests? No Problem! Must See Discounts!
Sleeps 18 · 7 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 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