Windward Cay, Kissimmee, FL, USA

Windward Cay, Kissimmee, FL, USA

We found 524 holiday rentals — enter your dates for availability


Find the best place to stay — Windward Cay

Where to stay around Windward Cay?

Our 2018 accommodation listings offer a large selection of 524 holiday lettings near Windward Cay. From 212 houses to 120 villas, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Windward Cay is on HomeAway.

What is the best area to stay when travelling to Windward Cay?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Windward Cay:

  • Highlands Reserve: 2,510 holiday homes
  • Florida Center: 88 holiday homes
  • Calabay Parc: 551 holiday homes
  • Lake Berkley: 1,372 holiday homes
  • Cumbrian Lakes: 262 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Windward Cay?

HomeAway offers a large selection of holiday accommodations near great places in Windward Cay. From HomeAway travelers, the most popular points of interest to stay near are:

  • Disney World: 33,499 holiday lettings
  • Universal Studios: 31,626 holiday lettings
  • ChampionsGate Golf Club: 32,805 holiday lettings
  • Lake Davenport: 32,786 holiday lettings
  • Orlando International Premium Outlets: 31,189 holiday lettings

But there are many other points of interest around Windward Cay listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent houses in Windward Cay?

Yes, of course. HomeAway offers 212 houses in Windward Cay. Our other popular types of Windward Cay holiday rentals include:

  • Villas: 120 self catering accommodations
  • Condos: 42 self catering accommodations
  • Apartments: 17 self catering accommodations

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

Can I find a holiday accommodation with pool in Windward Cay?

Yes, you can select your preferred holiday accommodation with pool among our 482 holiday homes with pool available in Windward Cay. Please use our search bar to access the selection of holiday rentals available.

    Holidaymakers searching for holiday rentals in Windward Cay also enquired about villas in Indian Point, villas in Eagle Pointe and villas in Doral Woods

    Make a holiday rental home or villa in Windward Cay, USA your home away from home

    Located just five miles east of the world-famous Walt Disney World Resort in Florida, Windward Cay villa are the perfect option for those seeking family accommodation near this top attraction, but do not want to be limited to the cramped confines of a hotel room. An attractive and peaceful location, Windward Cay offers Florida sunshine, a tranquil setting, and Disney on your doorstep. What more could you ask for?!

    Things to do in Windward Cay, USA

    Set amongst woodlands and lakes, Windward Cay is an ideal destination when it comes to the delights of Disney. The Walt Disney World Resort is just a short drive away, meaning you can be at Sea World, Universal Studios or almost any Disney attraction within minutes, but then have the full facilities’ of a holiday rental villa to return to after a hectic day. This is particularly ideal for families with young children, and those who struggle to manage in the limited space of a hotel bedroom.

    Windward Cay itself is an attractive area. Surrounded by pine forests and ranch land, the estate has an air of exclusivity about it, and makes for a pleasant walk during late evening, or for bird spotting during the daytime.

    Just a short walk from the main accommodation is the Highway 192 Resort Area. This has a full range of shops and leisure amenities, and also makes for a good night out, with a wide selection of restaurants, bars and entertainment options to choose from.

    Places to visit on holiday in Windward Cay, USA

    If you decide to have a day off from Disney, it makes sense to explore the surrounding area. From Windward Cay it is possible to get to beaches on either the east or west coast of Florida in around an hour. The surrounding Kissimmee area also has plenty to offer, being home to a huge number of golf courses, as well as the Historic Downtown area Kissimmee City itself, with it arts, culture and shopping attractions. The popular city of Orlando is also within easy reach.

    Weather in Windward Cay, USA

    Florida is well known for its tropical climate and the weather in Windward Cay is no different. Summers are hot and humid, and winters are warm with a drier heat. Temperatures below 20C are uncommon in this part of the world, but don’t panic if it becomes too hot- Disney’s Typhoon Lagoon Water Park is literally on your doorstep!

    Flights to Windward Cay, USA

    Orlando Airport (MCO) is just 30 minutes away, and is easily accessible to and from the Windward Cay villas. If you plan to visit the outlying areas of Kissimmee during your stay, you may wish to consider a hire car rental, with several firms to choose from within the airport terminal.