Windsor Island Resort holiday homes

We found 997 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Windsor Island Resort

Showing deals for:21 Nov - 28 Nov

Image gallery for Family-Friendly 5BR Home with Pool & Clubhouse Access

Sip, Sunbathe, and Splash: Your Perfect Florida Poolside Escape
9.2 out of 10 rating
Wonderful
(5 reviews)

Family-Friendly 5BR Home with Pool & Clubhouse Access

Davenport, FL

7% off
Price is NZ$4,273
NZ$610 nightly
Includes taxes & fees
Family-Friendly 5BR Home with Pool & Clubhouse Access

Image gallery for Stylish family friendly, 5 suites near Disney!

Pool
9.8 out of 10 rating
Exceptional
(8 reviews)

Stylish family friendly, 5 suites near Disney!

Davenport, FL

7% off
Price is NZ$4,529
NZ$647 nightly
Includes taxes & fees
Stylish family friendly, 5 suites near Disney!

Image gallery for Spacious 9BR Villa | Home Theater & Pool!

All aboard the adventure express! This train-themed room offers a magical escape for kids with bunk beds and scenic murals.
9.0 out of 10 rating
Wonderful
(17 reviews)

Spacious 9BR Villa | Home Theater & Pool!

Davenport, FL

7% off
Price is NZ$8,153
NZ$1,165 nightly
Includes taxes & fees
Spacious 9BR Villa | Home Theater & Pool!

Image gallery for Stunning 8BR Villa | Theater/Theme Rooms/Pool

Enjoy endless fun in this vibrant game room featuring a pool table, arcade games, and a cozy lounge area—perfect for family gatherings!
8.0 out of 10 rating
Very good
(6 reviews)

Stunning 8BR Villa | Theater/Theme Rooms/Pool

Davenport, FL

7% off
Price is NZ$6,404
NZ$915 nightly
Includes taxes & fees
Stunning 8BR Villa | Theater/Theme Rooms/Pool

Find spaces that suit your style

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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