Homes for Sale

Searching for holiday homes for sale in Kissimmee/Orlando? Windsor at Westside is a highly desirable vacation resort community located near Disney. Buyers will find beautiful single family homes and townhomes that are ideal for short-term and long-term rentals. Holiday guests enjoy their stay at Windsor at Westside because the gated community features some amazing amenities including a zero-entry pool, water slide and lazy river, fitness center, sports courts and video arcade. With easy access to the area theme parks, Windsor at Westside can’t be beat when it comes to holiday home communities in Central Florida.

Check out the available Windsor at Westside real estate listings below! Want to learn more? Continue reading for more information, or contact us online to reach a Windsor at Westside vacation home specialist!

Search Windsor at Westside Real Estate Listings


8803 Macapa Dr, Kissimmee

This beautiful property luxury home that comes furnished with professionally designed decor, and custom interior painting. Beautiful screene …more
2116 ROME DR,

2116 Rome Dr, Kissimmee

Turn-key for short term rental. This house locates next to club house in 1 minute walking distance in Phase I. Man-made lake in front of hou …more

2446 Tangier Dr, Kissimmee

Why wait for a new home to be built, when you can buy this 2019 brand new, turn-key VACATION HOME (short-term rental) in the sought-after ga …more

1504 Mumbai Way, Kissimmee

Don’t miss the opportunity to buy this 2019 brand new, turn-key VACATION HOME in the sought-after gated community of Windsor at Westside! Ex …more
2462 DUBAI ST,

2462 Dubai St, Kissimmee

Gorgeous vacation home in the Windsor at Westside Community! Minutes to Disney World, Universal, International Drive Retail/Shopping and oth …more
2464 DUBAI ST,

2464 Dubai St, Kissimmee

Gorgeous vacation home in the Windsor at Westside Community! …more
1844 GOBI DR,

1844 Gobi Dr, Kissimmee

Great opportunity this gorgeous and professionally furnished 6 bedroom home in Windsor at Westside . This home has 2 master suites and is p …more

Windsor at Westside Amenities

Among the reasons why buyers choose to purchase a holiday home in the Kissimmee community of Windsor at Westside is the vast array of amenities found here. Rental guests have the use of an expansive clubhouse which features a fitness center, sundry shop and video arcade. You can enjoy fun in the Florida sun with a swim in the zero-entry resort-style pool, waterslide, lazy river and kids’ splash playground. When you’re spending a day at the pool, there’s no need to leave to get a bite to eat because the resort has its own tiki bar and fireplace lounge, serving food and drinks for poolside dining. You’ll also find a multi-sports court, sand volleyball court, soccer field, and tennis courts, as well as a children’s playground.

The ideal location of Windsor at Westside gives you and your rental guests easy access to the Disney World® theme parks via State Road 429, as well as Orlando’s other popular attractions including SeaWorld, LegoLand, and Universal Studios. Plus, an hour’s drive away puts you at one of Florida’s popular beaches, such as Clearwater Beach and Daytona Beach.

There are a number of grocery stores and retailers within a 15 minute drive, including Publix, Wal-Mart and Target, where you can buy food, clothes, toiletries, and other supplies. When you want a break from home cooking, there are a number of dine-in and fast food restaurants near Windsor at Westside including Bonefish Grill, Bahama Breeze, Culver’s, and Chuy’s Mexican restaurant. Residents of the UK will feel right at home when dining at The Friar Tuck and Best of British Cafe & Pub.

Windsor at Westside Floor Plans

You’ll find a variety of styles and price points for the homes for sale in this Kissimmee gated resort community. Buyers seeking easy-to-maintain, affordable properties can choose between the four and five bedroom townhomes in Windsor at Westside. If you’re looking for more spacious accommodations, the neighborhood also offers six to nine bedroom single-family pool homes. Vacation home buyers will appreciate the quality features included in these properties, such as tile roofs, paver driveways, stainless steel appliances, open concept floor plans with ample storage, generous sized primary suites and game rooms. Let us help you find the perfect second home or short-term rental investment.

If you’d like to learn more about the available homes for sale in Windsor at Westside, please take a moment to contact the Donovan Team online or call 407.705.2616 to reach an experienced Windsor at Westside vacation home expert.