Ariel view of Windsor Hills Resort swimming pool and clubhouse

Windsor Hills Resort, Orlando

Fantastic vacation rentals near Disney World at Windsor Hills Resort

Windsor Hills Resort

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About Windsor Hills Resort vacation rentals

Located just moments away from Disney World, Windsor Hills Resort is the closest and most convenient Orlando resort for family vacations to the theme parks. Our stunning Windsor Hills vacation rentals are ideal for families or large groups, with space for up to 17 guests, plus all the amenities you could wish for.

One of Orlando’s premier gated resorts, Windsor Hills is a beautiful spot for a vacation and is as close to Disney World as you can get without physically being there. The resort is about 5 minutes drive from Disney and is situated close to Highway 192, making it ideal for exploring all of Orlando’s attractions. Windsor Hills also has fantastic amenities for guests of the resort, including health and fitness facilities and family activities.

With a fabulous selection of Windsor Hills rentals for vacations in Orlando, you can book a fantastic stay with us. Perfect for families or large groups, our Windsor Hills villas have excellent features and facilities, as well as access to all of the resort’s amenities.

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Windsor Hills 510 vacation home at sunset

Useful information for visiting Windsor Hills Resort and Orlando

When is the best time to visit Windsor Hills Resort Orlando?

As with all vacations, timing is everything when it comes to getting the best out of your stay at Windsor Hills Resort. Orlando is an extremely popular destination and attracts crowds year-round to the theme parks. School breaks and the weeks around the festive holidays are the busiest times to be there, so if you have any wiggle room at all, try and visit outside of these times. Outside of the holiday season, winter is a lovely time to stay at Windsor Hills Resort. Warm weather and winter sunshine make outdoor activities very enjoyable, and there are noticeably fewer crowds than in the peak summer months.

How do I get to Windsor Hills Resort from Orlando airport?

Either of Orlando’s major airports is within easy reach of Windsor Hills Resort. Orlando International Airport is a 30-minute drive along the 417. You can book a rental car with our handy Travel Extras service, or, if driving’s not your thing, you can also use it to arrange an airport transfer to your vacation home. 

Orlando Sanford International Airport is around 52 minutes away by car.

Is there parking at Windsor Hills Resort?

You can park one car in front of your vacation rental at Windsor Hills, with extra parking areas around the resort if you have more than one vehicle.

How do I book a vacation home at Windsor Hills Resort Orlando?

Booking a Windsor Hills Resort vacation home is very straightforward. Head over to our resort listing page and enter your travel dates to see which homes are available during that period. You can view individual home specifications by clicking on listings. Once you have chosen your dream Windsor Hills rental, you opt to hold the property or make an inquiry, in which case our fantastic Travel Planners will step in to answer any questions or queries you have about booking, and assist you with the process if needs be.

How do I access facilities at Windsor Hills Resort?

When you check in, you’ll be able to get a wristband that will allow you to access the pool and water park. Make sure you keep the wristband on for your entire stay or attach it somewhere safe and visible such as a hat, bag, or shoe. To get your wristband, head over to the Welcome Center at the Clubhouse.

Do the condo blocks have elevators?

Yes. The condo blocks all have elevators.

A view of Windsor Hills Resort swimming pool with sun loungers and patio area

Windsor Hills Resort Orlando amenities

An ariel view of Windsor Hills Resort swimming pool

Olympic-size resort swimming pool

Windsor Hills community pool is the focal point of the resort. Open daily from 8 am through 10 pm, it is a great place to cool off in the Florida sunshine. During the winter months, the pool is heated to 82 degrees Farenheight. There are showers and toilets that guests can use in the pool area.

Splash pad at Windsor Hills Resort


Windsor Hill’s waterpark is a firm favorite with families staying in the resort. With multiple waterslides, splash pads, pools, and more, the park is open year-round (weather permitting), from 10 am through 6 pm.

Children's play area shaped like a Medieval castle at Windsor Hills Resort

Children's play area

The children’s playground at Windsor Hills Resort is sure to be the favorite part of it for young guests. With slides, roundabouts, swings, and even a miniature castle to explore, there are enough attractions on offer to amuse and delight throughout your entire vacation.

Windsor Hills Resort putting green with covered seating are and flagged hole

Golf putting green

Florida is renowned for its world-class golf courses, and Windsor Hills Resort has got a putting green where you can practice your swing before heading out onto one of the fantastic nearby courses.

Tennis courts at Windsor Hills Resort

Tennis and volleyball courts

Entertainment options are never in short supply at Windsor Hills Resort, particularly for sports and fitness fans. The resort’s tennis and volleyball courts are an example of this, where guests can enjoy some friendly competition with their friends and family.

Windsor Hills Resort clubhouse, showing cushioned chairs around small circular tables on a tiled floor, with arched windows and doorways and a high ceiling with fans


Windsor Hill’s clubhouse is the place to go if you have any requests or queries about the resort amenities. It is right in the middle of Windsor Hills, and is open every day from 8 am through 10 pm. There are also showers and toilets for guest use in the clubhouse.

Windsor Hills Resort fitness center with treadmills and static cycles on a dark floor

Fitness center

Your gym schedule doesn’t need to drop off because you’re on vacation, as Windsor Hills Resort has got a well-appointed fitness center for guests’ use. With a great range of equipment for both cardio and strength work, the fitness center’s opening hours are from 6:30 am through 10 pm.

Windsor Hills Resort games room with a pool table, claw machine, arcade games and cards table

Games room

For those rare rainy days in Orlando, Windsor Hills Resort has got a fantastic games room, complete with video games, billiards, and table tennis to keep the whole family entertained.

Windsor Hills Resort shop display, with a sunglass rack, bottles and cans of drink, sun screen bottles and an inflatable pool donut


Whether you’re grabbing a snack to take to the theme parks or stocking up on supplies for your vacation rental kitchen, Windsor Hill’s onsite grocery store is a handy place to pick up some tasty treats.

Windsor Hills Resort movie theater, with rows of black chairs facing a blank screen

Movie theatre

Catch the latest blockbuster or classic favorites at Windsor Hill Resort’s surround-sound movie theatre.


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 Hills rentals with pools

Enjoy a refreshing dip in your own private pool at our Windsor Hills vacation rentals. The villas have lanai-covered areas with swimming pools and hot tubs, meaning that you can make the most of this fun facility even when the sun isn’t shining. There are sun loungers, tables, and chairs set up around the pool so that you can catch some rays while keeping an eye on the kids as they enjoy the water.

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Windsor Hills Resort rental 510 covered pool area

Types of Windsor Hills vacation rentals

From 2-bedroom homes for 5 people to rental homes sleeping up to 17 guests, we have a fantastic selection of Windsor Hills condos, townhouses, and large homes for groups of all sizes. So whether you're heading to Kissimmee for a family vacation at Disney, on a golf break with some friends, or looking for a Windsor Hills rental for a family reunion, sports team, or corporate getaway, you'll find it here. You can also rent side-by-side homes for more space.

If you're looking for Windsor Hills Resort rentals with specific amenities and features, look no further. Our fantastic vacation homes come with unbeatable amenities. From private covered pools and hot tubs to games rooms and home theatres for entertaining, there are plenty of ways to keep busy in these rentals. We also have Windsor Hills vacation rentals with pet-friendly facilities, so you can bring the whole family along for the Floridian adventure.

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.

Conde Nast Traveler
The Telegraph
The Times

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Windsor Hills vacation rentals with themed bedrooms

From pirates to princesses, superheroes to space and everything in between, our Windsor Hills vacation rentals with themed bedrooms are ideal for stoking the imagination. With spectacular features such as whimsical castle beds, wizard bunkbeds, and dino-discovery dens, these awesome themed rooms are sure to be the talk of your vacation and provide many happy memories to take home with you.

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Windsor Hills 218 princess room