Windsor at Westside holiday rentals

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September 2025

October 2025

Holiday rentals with weekly discounts - Windsor at Westside

Showing deals for:19 Dec - 26 Dec

Exceptional

(5 reviews)

Splash pool home near Disney World Orlando

Kissimmee, FL

28% off

for 7 nights, 1 home

AU$1,247 per night

includes taxes & fees

Excellent

(23 reviews)

Family Vacation Villa Near Disney with Themed Bedrooms, Game Room & Pool

Kissimmee, FL

7% off

for 7 nights, 1 villa

AU$760 per night

includes taxes & fees

Come enjoy our amazing resort amenities and have a drink at the Cantina!

Exceptional

(29 reviews)

Closest House to Resort • Star Wars Adventure + Home Theater!

Kissimmee, FL

8% off

for 7 nights, 1 home

AU$1,546 per night

includes taxes & fees

This green warp pipe slide teleports you from Moana to video game paradise.

Exceptional

(20 reviews)

Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩

Kissimmee, FL

8% off

for 7 nights, 1 home

AU$2,428 per night

includes taxes & fees

Exceptional

(28 reviews)

RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room

Kissimmee, FL

8% off

for 7 nights, 1 home

AU$1,323 per night

includes taxes & fees

Wonderful

(36 reviews)

NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside

Kissimmee, FL

8% off

for 7 nights, 1 villa

AU$1,109 per night

includes taxes & fees

Wonderful

(7 reviews)

New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

Kissimmee, FL

5% off

for 7 nights, 1 villa

AU$717 per night

includes taxes & fees

Bedroom 3 is has a plush queen-size bed and an ensuite bathroom.

Very good

(14 reviews)

Game Room | Private Pool | Gym | 19 Mins to Disney

Kissimmee, FL

8% off

for 7 nights, 1 home

AU$809 per night

includes taxes & fees

Excellent

(12 reviews)

NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

Kissimmee, FL

5% off

for 7 nights, 1 villa

AU$717 per night

includes taxes & fees

Located in Windsor at Westside Resort, where you'll get access to all its amenities.

Very good

(7 reviews)

Family Paradise Close to Disney w/ Resort Amenities!

Kissimmee, FL

7% off

for 7 nights, 1 home

AU$812 per night

includes taxes & fees

Exceptional

(10 reviews)

Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay

Kissimmee, FL

7% off

for 7 nights, 1 home

AU$1,392 per night

includes taxes & fees

Find spaces that suit your style

Find the best place to stay - Windsor at Westside

Premier Host

Modern Spacious Villa with No Rear Neighbors! Game Room, BBQ Grill, Kid Themed Bedrooms, Free Wi-Fi!

Sleeps 14 · 5 bedrooms · 5 bathrooms

Premier Host

Dream House Facing South with Lake View Next Disney World - Windsor at Westside

Sleeps 10 · 4 bedrooms · 3+ bathrooms

Premier Host

6BR Villa with Pool in Windsor at Westside Resort, Near Disney World

Sleeps 15 · 6 bedrooms · 4+ bathrooms

Premier Host

Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities

Sleeps 10 · 5 bedrooms · 4+ bathrooms

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