Discover a selection of 1,000 holiday rentals in Windsor Hills Resort, Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at £ 93 per night, and villas and houses are popular options for a stay in Windsor Hills Resort. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Windsor Hills Resort
Destination guide

Discover Orlando with Windsor Hills Resort holiday lets

Windsor Hills Resort is an exclusive gated community set in the heart of Kissimmee. The extensive grounds are studded with lush palms and dotted with glassy lakes. As well as luxe private facilities, you'll be less than 2 miles from Walt Disney World Resort, as well as other big-ticket theme parks, like Universal Orlando, SeaWorld and LEGOLAND. Whether you're planning a romantic couple's weekend or a fun-filled family getaway, villa rentals in Windsor Hills Resort provide a dream setting for enjoying Orlando.

Day trips

Best day trips near your Windsor Hills Resort villa rental

Your Windsor Hills Resort holiday rental is a gateway to Orlando, the "Theme Park Capital of the World". You can snap selfies with Mickey Mouse in Disney World's Magic Kingdom Park, make a splash at Universal's Volcano Bay, enjoy multigenerational fun at LEGOLAND and more. Golfers can tee off at more than 150 courses, while wildlife lovers will jump at the chance to spot alligators on an airboat tour of the Florida Everglades.

Essential info

Essential info for your Windsor Hills Resort stay

  • Stock up on US dollars before you enter the parks, as many ATMs charge extra fees
  • Consider investing in a Go Orlando Card to unlock fantastic savings on top attractions
  • Booking theme park tickets in advance can be a great way to save
  • Pack a hat and plenty of sunscreen, as Orlando temperatures can climb well into the 30s
  • A reusable water bottle is a great way to save on plastic and stay hydrated in the Sunshine State
  • Venture beyond the theme parks to discover offbeat Orlando neighbourhoods, like Thornton Park and Ivanhoe Village

Luxury shopping near your Windsor Hills Resort holiday let

Craving a dose of retail therapy? You've come to the right place. Windsor Hills Resort villa rentals offer easy access to some of America's top discount malls, including Lake Buena Vista Factory Stores and Orlando International Premium Outlets. The Mall at Millenia is brimming with designer boutiques, like Prada, Versace and Tiffany & Co, while Disney Springs and the Universal CityWalk keep the magic alive with themed-shops and merchandise stores.

Family friendly

Family-friendly fun with Windsor Hills Resort holiday lets

As well as easy access to Orlando's top theme parks, holiday homes in Windsor Hills Resort treat guests to a bevy of family-friendly facilities, including a double-Olympic-sized swimming pool, tennis courts, 40-seat movie theatre, outdoor picnic area and more. This means that even when you're enjoying a rest day, the kids will still be well-entertained. Disney-themed bedrooms, private pools and spacious kitchens are the icing on the cake.

Good for couples

Romantic escapes with Windsor Hills Resort villa rentals

Thought Orlando was just for families? Think again. You can ride white-knuckle roller coasters at Universal Orlando, enjoy champagne and charcuterie boards in Disney Springs, and indulge at luxury day spas. After a day of theme park-hopping, enjoy poolside cocktails back at your Windsor Hills Resort holiday villa. Visit outside the US school holidays to beat the crowds and maximise the romance factor.

How many holiday rentals are available around Windsor Hills Resort?

Our 2021 accommodation listings offer a large selection of 1,117 holiday lettings around Windsor Hills Resort. From 218 villas to 868 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent Villas near Windsor Hills Resort?

Yes, of course. Vrbo UK has 218 Villas near Windsor Hills Resort. Our other popular types of holiday rentals near Windsor Hills Resort include:

  • Houses: 868 holiday lettings
  • Townhouses: 224 holiday lettings
  • Flats: 249 holiday lettings

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool near Windsor Hills Resort?

Yes, you can select your preferred holiday accommodation with pool among our 1,092 holiday rentals with pool available near Windsor Hills Resort. Please use our search bar to access the selection of self catering accommodations available.