Windsor Island Resort, Orlando

Find the perfect villa in Windsor Island Resort for your next vacation

Windsor Island Resort

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Windsor Island Resort vacation rentals

One of the newest resorts in Orlando, Windsor Island is a fantastic place to stay for visiting theme parks and enjoying countless amenities guaranteed to bring family fun. Located in the Davenport area, Windsor Island is the sister resort to the popular Windsor At Westside, and much of what makes that resort a firm favorite with families and groups have been replicated at Windsor Island.

Chic, stylish, and perfect for group vacations, our Windsor Island Resort rentals are wonderful places to sta in Orlando. With in-home amenities including private pools, themed bedrooms, games rooms, hot tubs, and home theaters, they have everything you could ever need for an unforgettable vacation, along with access to all the resort facilities. And our reasons to stay don’t end there - Windsor Island Resort rentals are close to all of Orlando’s most popular attractions, including Disney World, Universal Studios, and the city’s shops and restaurants. 

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Windsor Island Resort 63

Useful information for visiting Windsor Island Resort

When is the best time to visit Windsor Island Resort?

Florida is a fabulous destination year-round, but depending on what you want from your vacation, there are definitely better times to stay at Windsor Island Resort. If you want to avoid the biggest crowds, steer clear of the peak summer season between July and September, as well as the Holiday period which also gets busy with families celebrating the festive season. For small crowds, try to visit outside of these times. January to March is usually one of the quieter periods in Orlando, along with late September through to Thanksgiving.

Weather-wise, Windsor Island Resort follows the same rules as the rest of Orlando. Boasting mild-to-hot weather all year round, it is a fantastic place to visit in winter when much of the rest of the USA shivers under thick blankets of snow. From June through October, Orlando is in its rainy season, when short, sharp, and sometimes stormy showers make a good raincoat a necessity. Generally, the best of the weather can be found in late winter through mid-spring.

How do I get to Windsor Island Resort from Orlando Airport?

Orlando International Airport (MCO) is quite close to Windsor Island Resort, with a driving time of 25 minutes between the two. The 20.3-mile journey involves toll roads, so make sure that you have your preferred form of payment ready before you set off from the airport. Driving is the easiest way to get from the airport to the resort, and also has the benefit of giving you the freedom to explore Orlando during your stay. You can either pick up a rental car from the airport, or you can organize your car hire through our Travel Extras service. 

If driving isn’t for you, we can also arrange for a private transfer to take you from the Arrivals Hall to the door of your Windsor Island Resort rental. Head over to our Travel Extras page, or get in touch with our brilliant, knowledgable Travel Planners to arrange a transfer.

Is there parking at Windsor Island Resort?

Complimentary self-parking is available with all Windsor Island Resort vacation rentals.

How do I book a Windsor Island Resort rental?

Booking your Windsor Island Resort rental couldn’t be easier! Simply head over to our Windsor Island listing page, and enter your travel dates to see which homes are available. Once you have found your perfect vacation home, you can reserve it for your dates, hold the property while you decide, or get more information on the villa from our fantastic Travel Planners.

Is there a shuttle service from Windsor Island Resort to Disney World?

Windsor Island does not currently offer a shuttle service from the resort to Disney World, but it is still very easy to get to the parks. We recommend renting a car for your Orlando vacation because this will give you the most amount of freedom and opportunity to visit all of Orlando's fantastic attractions. To organize a car rental for your trip, speak to our Travel Planner team today.

How close is Windsor Island Resort to Disney World?

Windsor Island Resort is very close to Disney World, with Epcot being just 6.7 miles away. It takes under 20 minutes to drive from the resort to any of the Disney parks.

Windsor Island Resort entrance

Windsor Island Resort amenities

Windsor Island Resort pool

Zero-entry resort pool

Ariel view of Windsor Island Resort and lazy river

Lazy River

Submerged sunbeds at Windsor Island Resort

Pool deck and sunbeds

Splash pad at Windsor Island Resort

Children's waterpark and splash pad

Double slide at Windsor Island Resort

Double slides

Spa equipment including towels and candles


Drinks at the Windsor Island covered bar

Covered bar

Brightly colored swings in a children's playground

Children's play area

Mini golf course at Windsor Island Resort

Mini golf

Windsor Island Resort basketball

Basketball courts

Sand volleyball net

Sand volleyball

Cornhole board and bags

Dual cornhole court

Woman reading a book in a hammock

Hammock garden

Windsor Island Clubhouse

Windsor Island Clubhouse

Fitness room at Windsor Island Resort with workout equipment

Fitness room

Playing air hockey

Games room


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 Island Resort vacation rentals with private pools

Is there anything more relaxing than a cooling swim in the heat of the Florida sunshine? We don’t think so, which is why we love that our beautiful Windsor Island Resort vacation rentals come with their own private pools, exclusively for the use of you and your loved ones. After a long day of exploring the Disney World parks, you can guarantee a lovely dip in the cool waters to relax your muscles and prepare for the next day of fun.

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Windsor Island Resort 95 covered pool area

Windsor Island Resort vacation rental amenities

Windsor Island Resort vacation rentals are fantastically well-equipped for every type of traveler. Whether you're heading to Florida on a golfing vacation, celebrating a family reunion, or on a family trip to the theme parks, the rentals at Windsor Island Resort have everything you need for an unforgettable vacation with your loved ones.

Windsor Island rentals are perfect for entertaining guests of all ages, with games rooms, home theatres, and private pools all on offer at the properties. Themed bedrooms featuring a host of favorite characters are sure to delight young guests, while spacious living and dining areas make excellent focal points for family meals and occassions.

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 Island vacation vacation homes with themed bedrooms

Imagine the excitement on the kids’ faces when they arrive at a Windsor Island Resort vacation rental and discover that their bedrooms are themed around their favorite movies and characters. From outer-space sagas to ice princesses, our villas with themed rooms capture all of the magic of a Disney vacation before you even step foot in the park.

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Windsor Island Resort 96 dinosaur-themed bedroom