Lazy river
Float through the resort's lazy river at the Windsor clubhouse.
Some days are for Disney magic; others are for floating along the lazy river and letting the children splash to their hearts’ content. Windsor at Westside gives you room for both. Come back to your own private screened pool, settle into a comfortable evening with the family and wake up ready for another day of Florida fun.

Resort amenities are available to guests staying in the community. Specific home features vary by property — check your chosen listing for details.
Float through the resort's lazy river at the Windsor clubhouse.
Water slides and a large resort pool for days when you don't want to drive anywhere.
Every home we manage has its own private pool in addition to the community amenities.
Poolside Tiki bar and hot tub at the clubhouse, alongside the heated pool and lazy river.
A well-equipped gym at the clubhouse for guests who want to keep active.
Our team manages each home directly and is reachable before and during your stay.
Windsor at Westside is a gated community in Kissimmee with a well-equipped clubhouse: gym, TV lounge, arcade, heated pool, lazy river, waterslides, splash area, hot tub, Tiki bar and sports courts. Walt Disney World is about 14 miles away, SeaWorld is around 18 miles, and US-192 dining and Sunset Walk are a short drive. Our team manages each home directly and is reachable before and during your stay.

Approximate driving distances from Windsor at Westside, Kissimmee. Actual mileage depends on the home, destination and route.
About 18–22 min drive via US-192.
Universal Studios Florida & Islands of Adventure.
Theme park adventures south of International Drive.
Orlando International Airport via FL-417.
Casual dining and fast food on the US-192 corridor.
Shopping, dining and entertainment at Disney Springs.
What Guests Say
4.91
471 reviews
Amazing home perfect for my party of 6! Rooms were large and spotless, with a spacious kitchen, living area and pool, just what you need after a long day exploring Florida! <br/>I’ve stayed at Watersong many times over the years, and I highly recommend this community. It’s a beautiful place, large enough to not feel overlooked or close to neighbours, yet not too far out of Orlando and you really do get that feel of “being a local” unlike many other estates that are primarily tourist homes…. (Plus there’s a large community pool & spa here too)<br/>Thanks to Jennifer for hosting us - always on hand to quickly answer questions and give advice.
Stayed in October 2026
We had a great time! The pool & outside area is great! The house was neat, clean & well taken care of. The pictures are very accurate. When we arrived there was an issue with the downstairs AC. Jennifer was extremely responsive & helpful. Within a couple of hours the problem was fixed.<br/>We would definitely stay here again!<br/>Yitz
Stayed in October 2026
A house is only as good as its hosts, and we really appreciated how responsive our hosts were. There were a few minor issues during our stay, but they were dealt with immediately. The effort and communication from the hosts made the stay worth it.
Stayed in September 2026
The house was absolutely stunning and very clean. The house was cozy and felt like you were coming home at the end of the day. The pool was clean and the perfect bit of relaxation. I loved sitting outside on the lounging chairs while reading a book and watching the lizards run around outside the netting.
Stayed in September 2026
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Before You Book