Windsor at Westside holiday rentals

We found 1,032 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

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$1,257 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$751 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$1,543 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$2,409 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$1,321 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$1,108 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$716 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$807 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$716 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$821 per night

includes taxes & fees

Exceptional

(10 reviews)

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

Kissimmee, FL

6% off

for 7 nights, 1 home

AU$978 per night

includes taxes & fees

Exceptional

(14 reviews)

Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney

Kissimmee, FL

8% off

for 7 nights, 1 home

AU$654 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor at Westside

Premier Host

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

Sleeps 10 · 4 bedrooms · 3+ bathrooms

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

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

Peace of mind
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