Windsor Hills holiday homes

We found 2,831 holiday rentals — enter your dates for availability

Select from 999 houses, 335 flats and other holiday rentals to find the perfect place for your stay in Windsor Hills. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Windsor Hills

Showing deals for:13 Feb - 20 Feb
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Windsor Hills

  • Family-friendly entertainment: Windsor Hills is close to major theme parks, perfect for creating unforgettable family memories.
  • Recreational activities: Enjoy various outdoor pursuits like golf, fishing, and picnicking by scenic lakes.
  • Vibrant community atmosphere: Experience the warm hospitality of friendly locals in a lively neighbourhood.
  • Relaxing outdoor spaces: Unwind in beautiful parks and gardens, ideal for a quiet retreat after adventurous days.
  • Convenient location: Windsor Hills offers easy access to nearby attractions, making it a perfect base for exploration.

Top attractions near Windsor Hills

Windsor Hills is an ideal destination for families seeking outdoor and entertainment adventures. With a variety of attractions like theme parks, scenic lakes, and golf courses, there's something for everyone to enjoy. Whether you're travelling with the whānau or friends, you’ll find plenty of activities to keep you entertained and create lasting memories during your stay in this vibrant community.

  • Walt Disney World® Resort: A magical theme park experience just 11.3km from Windsor Hills, featuring enchanting attractions, beloved characters, and vibrant entertainment for the whole family. It's a place where dreams come true.
  • Orange County Convention Center: Located 16.1km away, this arts centre is a hub of cultural events, exhibitions, and shows, showcasing a diverse range of artistic talents and experiences.
  • ChampionsGate Golf Club: Only 6.4km from Windsor Hills, this family-friendly golf course offers stunning fairways and welcoming staff, perfect for a relaxing day of golf or excursions.

Things to do recommended for couples

For a romantic getaway in Windsor Hills, enjoy a fun round at Disney's Winter Summerland Miniature Golf Course, just 4.8km away. Alternatively, head to Pirate's Dinner Adventure, 19.3km away, for a delightful dining experience filled with city vibes and romance. Perfect for couples.

Things to do recommended for families

Families will love the thrilling atmosphere at ESPN Wide World of Sports Complex, just 4.8km from Windsor Hills. For a splash of fun, Disney's Typhoon Lagoon Water Park, located 8.0km away, offers excitement and adventure. Don't miss the karting experience at Kissimmee Go-Karts, 12.9km away.

Things to do recommended for groups

Your group can enjoy shopping and dining at Disney Springs™, only 9.7km from Windsor Hills. For some outdoor fun, head to Highland Reserve Golf Club or Disney's Osprey Ridge Golf Course, both 5 and 9.7km away, offering a fantastic golfing experience surrounded by nature.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Windsor Hills

If you're heading off on an adventure with friends, family, pets, or planning an extended stay, be sure to refine your search based on what matters most to you. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windsor Hills with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for socialising with your group. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Windsor Hills with young kids: Travelling with little ones can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s worth thinking about how close you are to family-friendly activities.
  • Taking your pets with you to Windsor Hills: For many families, a holiday isn’t truly special without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Windsor Hills

Windsor Hills is a fantastic spot for a family holiday in Florida, offering a vibrant atmosphere filled with friendly locals and plenty of recreational activities. Just a stone's throw away from thrilling theme parks, you'll find a range of family-friendly excursions and relaxing outdoor spaces. Whether you're after exciting adventures or a quiet retreat, Windsor Hills and its surrounding areas provide the perfect blend for an unforgettable getaway.

  • Orlando: Orlando is a vibrant metropolis known for its family-friendly atmosphere and entertainment offerings. As the home of Windsor Hills, it provides easy access to a plethora of attractions. Visitors can enjoy world-renowned theme parks, including Disney World and Universal Studios, alongside shopping areas that cater to all tastes. The city boasts a rich cultural scene with arts centres showcasing local talent. Additionally, outdoor enthusiasts will appreciate the beautiful parks and nearby beaches, making Orlando a well-rounded destination for all ages.
  • Four Corners: Four Corners is a charming village that shares its appeal with Windsor Hills. This area is perfect for families seeking an entertaining getaway, with several resorts and golf courses nearby. Four Corners serves as a convenient base to explore local attractions, including theme parks and film studios. Sports fans may also enjoy the proximity to local stadiums, making it an ideal spot for those looking to combine relaxation with excitement. The tranquil atmosphere coupled with easy access to attractions makes Four Corners a delightful place to visit.
  • Crestwynd Bay: Crestwynd Bay is a welcoming neighbourhood located a mere 483m from Windsor Hills. This area is ideal for families, offering a balance of entertainment and outdoor activities. Crestwynd Bay features various resorts, shopping areas, and golf facilities, ensuring visitors have plenty to do. Local landmarks, such as theme parks and film studios, are just a stone's throw away, while nearby stadiums provide additional entertainment options. The close-knit community feel and convenient location make Crestwynd Bay a fantastic spot for a memorable holiday experience.

Best time to go to Windsor Hills

If you're planning a trip to Windsor Hills, it's a good idea to check both the weather and property rates. The warmest month is August.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly High
February64.4°F (18.0°C)Light RainMostly SunnyAverage
March67.6°F (19.8°C)Light RainMostly SunnySlightly High
April72.7°F (22.6°C)Light RainMostly SunnySlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverage
August82.6°F (28.1°C)Moderate RainMostly SunnyAverage
September80.4°F (26.9°C)Moderate RainMostly SunnyAverage
October75.2°F (24.0°C)Light RainMostly SunnySlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly Low
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnySlightly Low

Booking with Vrbo is a breeze

Are you keen to save some dollars on your upcoming getaway? Being open to changing your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, don’t hesitate to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for you to plan your trips, resume where you left off, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Windsor Hills?
Season, property type and length of stay are some of the things that can affect the price of a holiday home. Simply add your travel dates to find your perfect escape. From homey country cottages to expansive villas, all Bookabach holiday homes offer terrific value.
How much does it cost to rent a beach house in Windsor Hills?
When you travel and the style and size of the property will help determine the cost of your beachside holiday home. Put in your Windsor Hills travel dates to see your options on Bookabach. Can't live without a private pool? Use our filters to select the amenities and features you want in your beach house.
What are the top attractions for families in Windsor Hills?
Keep your kids occupied at these fabulous family-friendly attractions in Windsor Hills:

  • Surfari Water Park
  • Northeast Regional Park
  • Lake Davenport

How old do you have to be to rent a holiday home in Windsor Hills?
The minimum age requirements can differ across properties on Bookabach, so check the rules of the holiday home in Windsor Hills you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Windsor Hills for?
The amount of time you can stay in a Windsor Hills holiday home for is down to the property. Just tap in your dates of travel to view options offering longer term stays. They feature everything you need to make your extended break more comfortable and enjoyable, like air conditioning and kitchens. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.

More Holiday Rentals ideas

People also search for