Recommend Rentals
9 bedrooms · 6 baths · 18 guests
From $229.00 / night
Explore Windsor at Westside vacation rentals in Kissimmee, Florida, in the Orlando theme-park area. Florida Vacation Homes offers a selection of homes in this gated resort community, with options for family vacations and larger groups. Compare the recommended homes below, then search your dates to find a rental that suits your party.
9 bedrooms · 6 baths · 18 guests
From $229.00 / night
8 bedrooms · 6 baths · 16 guests
From $169.00 / night
Featuring an extraordinary 10,000 sq.ft. clubhouse, lake & pier, zero-entry resort-style pool complete with a waterslide, lazy river, and Kids’ water playground. The Tu Casa Tiki bar & fireplace lounge serves food for poolside dining. There is also a fitness center, volleyball courts, and a sundry shop and video arcade. The ideal location offers easy access to the Disney World® theme parks via toll road 429. Also, close by are many dining and shopping options. Windsor at Westside Resort includes single-family pool homes in addition to townhomes ranging in size from 4 bedrooms to 9 bedrooms. For a day away from the theme parks, explore Florida’s beaches, including Anna Maria Island.
If you’re looking to contact the resort directly please visit the contact page.
A family trip works better when the home fits the way you travel. Windsor at Westside offers townhomes and single-family pool homes, with properties across the resort ranging from 4 to 9 bedrooms. Start with your dates and guest count, then compare sleeping arrangements, bathrooms and the spaces where everyone will spend time together.
A townhome is worth comparing when you want separate bedrooms and shared living space for a family stay. For an extended-family vacation or a trip with friends, a larger villa gives you more bedrooms to divide between households. Check the individual listing for its maximum occupancy and bed sizes; bedroom count alone does not tell you how comfortably your group will fit.
| Your priority | Check the property listing for |
|---|---|
| A stay with several families | Bed sizes, bathroom count, dining space and the maximum number of guests. |
| Time by your own pool | Pool and patio photos, safety features, and any optional pool-heating charges. |
| Entertainment at home | Themed bedrooms, games rooms and equipment shown for that specific home. |
Looking for an 8- or 9-bedroom Windsor at Westside villa? The Recommended Vacation Homes above provide a starting point. Browse Windsor at Westside rentals to compare the available homes for your travel dates.
Windsor at Westside is in Kissimmee, Florida, in the Orlando vacation area. Use your rental as a base for theme-park days, then leave time in your itinerary for the resort pool or an evening at home. Plan each journey to the park you intend to visit: travel time varies with traffic, your route and the park entrance, so a single drive-time estimate can be misleading.
Before you book, review the full stay total, cancellation terms and any optional extras. For a group trip, share the property photos and bedroom layout with everyone before choosing. Our Windsor at Westside photo gallery shows the resort amenities; each rental listing has photographs of the individual home.
Yes. The resort’s shared pool area includes a lazy river, waterslide and children’s water playground. These are community facilities, separate from a rental home’s private pool. See the Windsor at Westside amenities guide for more about the clubhouse and recreation facilities.
Check the individual home’s description and photos for its pool, outdoor seating and any spa. Confirm whether pool heating is available and what it costs before booking. Features and optional services can differ between properties.
This website is a marketing brand of Florida Vacation Homes, an independent vacation rental management company. We offer a selection of homes within Windsor at Westside; we do not operate the resort’s shared amenities. Contact us for help choosing a rental or finding the appropriate resort contact.
Find the right home for your family.
WindsorWestsideOrlando.com is a marketing brand of the established property management company Florida Vacation Homes. Our local property care team is on hand to assist you during your stay to deliver your memorable Orlando vacation experience.
Orlando
Kissimmee area
7531 Osceola Polk Line Rd
Davenport, FL 33896
Office: 407-545-5830