Windsor at Westside Resort

Windsor at Westside Resort, Orlando

Find the perfect villa at Windsor at Westside Resort for your next vacation

Windsor at Westside Resort

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Stunning Windsor at Westside vacation rentals

This beautiful resort-style community, located in West Kissimmee, Florida, is the ideal place for relaxing vacations with family and friends. Offering guests full use of all the excellent on-site facilities, including large swimming pools, a clubhouse, and a lazy river, Windsor At Westside Resort has plenty to keep the whole family entertained.

For when you want to venture out and about, Disney World is only a short drive away, as are the shops and attractions of Central Florida. Suitable for families and large groups, the properties are bright, modern, and stylish, with a host of great facilities to enjoy. Features include private pools, games rooms, home theaters, and pet-friendly facilities, making them perfect for fun-filled family vacations in Orlando.

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Windsor at Westside 230 vacation rental - a large villa painted grey and white with a manicured front lawn and palm trees out front

Useful information for visiting Windsor at Westside

How far is Windsor at Westside from Disney World?

The drive from Windsor at Westside Resort to Disney World is quick and simple. The closest park is Animal Kingdom, with the drive taking approximately 22 minutes in good traffic, covering just under 10 miles.

How long is the drive from Windsor at Westside to Magic Kingdom?

The drive between Windsor at Westside to Magic Kingdom takes around 27 minutes in good traffic and covers 14 miles.

How far is Windsor at Westside to Universal Studios?

Universal Studios is 22 miles away from Orlando Windsor at Westside, with a drive time of around 35 minutes in good traffic.

Is there transportation to and from Disney World?

Currently, Windsor at Westside Resort doesn’t offer its own shuttle service to and from the Disney parks. However, getting there is still simple and straightforward when you book with us. Once you have got your vacation rental booking sorted, get in touch with a member of our friendly Travel Planner team to organize your travel to and from the parks. Alternatively, if you would like to enjoy your vacation in complete and total freedom, we can also help you organize a car to keep for the duration of your getaway.

How to get from Windsor at Westside to the main airport?

The main airport in Orlando is Orlando International Airport (MCO), which is located to the southeast of the city center. Windsor at Westside, on the other hand, is located in the southwest on the outskirts. There are two main ways to get between the two, the quickest being via the FL-528. It takes 39 minutes on average  and covers 30.3 miles, although be aware there is a toll on this route. The alternative way to get between the two is by using the FL-417. This route is typically 41 minutes, covering 34.9 miles, and also has a toll, put passes a Publix, Walmart and Target.

When is the best time to visit Windsor at Westside Florida?

If you can, we recommend traveling in spring or fall. The weather at these times of year is utterly glorious, and you will find that it is not quite so busy as peak months, so you can enjoy Orlando at its very best. 

The two most important things to consider when deciding when to visit Windsor at Westside Orlando, is the weather and how busy it might be. In the summer months, temperatures can soar, which means you will need to take extra steps to ensure you keep hydrated and protect your skin from the sun. There is also a good chance of sudden downpours, though, as they are warm and tend to occur in short bursts, they shouldn’t affect your vacation adversely. THe other thing to consider of the summer months, is whether you mind an increase in crowd size. Especially in the theme parks, you may find them to be very busy, and wait times for rides will be increased. This is because summer is a popular time for tourism due to being on break from school and work. This is also true of other times such as the festive period, and spring break.

aerial view of orlando

Windsor at Westside amenities

view of windsor at westside pool

Windsor at Westside gated community

Windsor at Westside offers a 24-hour monitored entry gate, meaning you and your family can enjoy a peaceful stay in the utmost of privacy and security.

windsor at westside pool

Windsor at Westside pool

What better place to cool off from the heat of the Floridian days than in the large swimming pool at Windsor at Westside? Dip your feet in as you sip a drink or enjoy some laps - the choice is yours.

windsor at westside white and brown clubhouse

Windsor at Westside clubhouse

The 10,000 square foot Windsor at Westside Resort clubhouse is at the heart of the resort. Jam-packed full of facilities and amenities, head here to enjoy the resort to its fullest, and for any questions or queries.

outdoor sofa and fireplace

Tiki bar

The Tu Casa tiki bar is the perfect spot to unwind after a blissful day in the sun. Located poolside, you can also grab snacks, as well as your favorite beverages. At night, the bar transforms into a super cozy fireplace lounge.

cabana next to lake

Cabana rentals

If you’re hoping for a day lazing by the pool, make it an extra special occasion by hiring a private cabana for yourself and your family. These offer both comfort and privacy to make the most of your vacation.

children's splash park

Children’s splash park

Windsor at Westside offers the ultimate facilities to keep the little ones entertained, featuring a child’s splash park that comes with a slide and lazy river.

running on treadmill

Fitness center

Keep up with your fitness routine and keep hitting those personal bests when you stay at Windsor at Westside. On offer here is a fully-equipped fitness center.

sports court

Sports courts

It’s not just a fitness center where you can work up a sweat. If you prefer to get your exercise with a game or two of something, then head to the resort’s sports court.

neon arcade game


Settle a few friendly rivalries (or get a few started) with a visit to the resort’s arcade. Packed full of thrilling games to make you lose track of the hours.

top shot of bowls of snacks

Snack shop

Perfect for picking up any last minute treats for that movie marathon you have planned, or a few bits and bobs for dinner, there is an onsite sundry shop for your convenience.


Our dedicated and knowledgeable Travel Planners will be on hand to help you from the moment you book and throughout your stay


We offer you the best selection of homes in beautiful destinations and trending hotspots


Expect excellence as standard, giving you the top-quality you deserve every time you stay

Windsor at Westside vacation rentals with themed rooms

Our Orlando vacation homes are truly incredible - that’s no secret - but there is something that makes them even more unique and wonderful for family vacations; themed rooms! At the Windsor At Westside Resort in Kissimmee FL you can find homes with themed bedrooms and games rooms, featuring favorite characters and designs inspired by movies and game franchises. These fun rooms are perfect if you’re traveling with kids or visiting Disney World or Universal Studios, because they bring a touch of magic to your vacation rental, creating a stay that everyone will be talking about for years to come.

Find Windsor at Westside themed bedrooms
Windsor at Westside 340

How to book our Windsor at Westside resort villas

Booking one of our Windsor at Westside Resort vacation rentals is as easy as can be. Simply scroll to the top of this page to the search bar at the top, where you can enter the dates of your vacation and hit “search”. You will be directed to a new page, which will display every single one of our Windsor at Westside houses that are available for your chosen dates. 

Have a good browse, and when you have found one you love, you can book instantly by putting down a small deposit, by clicking “choose”. Or, if you have any questions or queries you would like answering before you secure your vacation rental, you can click “make an inquiry”, and a member of our friendly Travel Planner team will be in touch to help you

Book with Confidence

With over 100,000 happy guests every year and international media writing about our incredible homes and service, you can book your next stay with us with total confidence.

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Windsor at Westside Resort villas with games rooms

Family fun is the name of the game at our Windsor at Westside rentals with games rooms. From retro arcade-style games to foosball and mini-basketball shooters, these games rooms are stuffed full of ways to get the competitive spirit racing.

Many of our games rooms also have a theme, and are fantastic places for both kids and grown ups to let off some steam. Our Windsor at Westside houses with games rooms bring the famous fun of Orlando into your vacation rental.

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Windsor at Westside 32 games room