Windsor at Westside Resort 1134 vacation rental

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.

Large lake surrounded by trees amongst the skyscrapers of Downtown Orlando

Distances from Windsor at Westside Resort

AttractionDistance from Windsor at Westside (miles)Approximate driving time (minutes)
Magic Kingdom1427
Animal Kingdom9.922
Hollywood Studios11.423
Disney Springs1429
Universal Studios22.235
Orlando city center2127
Orlando International Airport28.534

Resort Amenities

  • Windsor at Westside pool and cabanas
    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 community 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  clubhouse exterior
    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.

  • Windsor at Westside  bar with couches
    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.

  • Windsor at Westside cabana by the 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.

  • Windsor at Westside splash pad
    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.

  • A person in orange sneakers on a 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.

  • Windsor at Westside tennis 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.

  • An arcade machine
    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.

  • An assortment of chips
    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.

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Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

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Windsor at Westside vacation rentals with Concierge

Our optional Concierge Services take Windsor at Westside vacation rentals to the next level. From private chefs to attraction tickets, and grocery deliveries to character home visits, there are so many options to choose from. Explore our Concierge page, or get in touch with our Travel Planners today.

Types of Windsor at Westside vacation rentals

Windsor at Westside vacation rentals with themed rooms - Windsor at Westside 32 Sta Wars themed bedrooms

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.

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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Windsor at Westside 32 game room with pool table and indoor basketball

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.