Windsor Island Resort holiday rentals

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September 2025

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Holiday rentals with weekly discounts - Windsor Island Resort

Showing deals for:19 Dec - 26 Dec

Exceptional

(48 reviews)

Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!

Davenport, FL

8% off

for 7 nights, 1 villa

AU$1,588 per night

includes taxes & fees

Enjoy endless fun in this vibrant game room featuring a pool table, arcade games, and a cozy lounge area—perfect for family gatherings!

Very good

(6 reviews)

Stunning 8BR Villa | Theater/Theme Rooms/Pool

Davenport, FL

8% off

for 7 nights, 1 villa

AU$1,182 per night

includes taxes & fees

Exceptional

(14 reviews)

Magical 5BR Villa - Game Room, Themed Rooms & Pool in Windsor Island

Davenport, FL

8% off

for 7 nights, 1 home

AU$805 per night

includes taxes & fees

Exceptional

(11 reviews)

Just Listed! 5BR Luxury Stay @ Lazy River Resort w/ Pool — Book 7 Nights & Save!

Davenport, FL

8% off

for 7 nights, 1 home

AU$871 per night

includes taxes & fees

Exceptional

(8 reviews)

5-BR Luxury Villa with Pool - Disney Delight - Windsor Island - 3312 LW

Davenport, FL

7% off

for 7 nights, 1 home

AU$792 per night

includes taxes & fees

Counter seating for 4 is available off the spacious, updated kitchen

Exceptional

(12 reviews)

Adventure of a Lifetime! 5 BDR at Windsor Island

Davenport, FL

8% off

for 7 nights, 1 home

AU$962 per night

includes taxes & fees

Experience cosmic dreams in this space-themed bedroom, featuring a stunning mural and modern comforts.

Exceptional

(6 reviews)

Disney Magic Villa | 5BR with Private Pool

Davenport, FL

7% off

for 7 nights, 1 home

AU$701 per night

includes taxes & fees

Very good

(5 reviews)

Spacious 5-bedroom townhome with WiFi, fitness room in welcoming Davenport

Davenport, FL

7% off

for 7 nights, 1 home

AU$742 per night

includes taxes & fees

Very good

(8 reviews)

Modern 10BR Gamer Villa w/ Star Wars Theater, Arcade, Pool + Themed Bedrooms

Davenport, FL

7% off

for 7 nights, 1 home

AU$1,867 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Windsor Island Resort

Premier Host

Luxury 6BR near Disney, Pool, Jacuzzi, Game & Theme Room

Sleeps 13 · 6 bedrooms · 4+ bathrooms

Premier Host

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

Premier Host

AMZNG Townhome with Heated Pool - 5B 4.5B - Windsor Island Resort near Disney

Sleeps 10 · 5 bedrooms · 4+ bathrooms

Lazy river - probably the longest among the resort in the area.

Premier Host

“Aloha Retreat” Pool Villa in Luxury Resort, FREE Pool Heating +Grill +Game Room

Sleeps 14 · 6 bedrooms · 4+ bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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