Windsor Hills vacation rentals

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Select from 977 houses, 333 condos, and other vacation rentals to find the perfect place for your stay in Windsor Hills. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for spending time at your vacation home, including air conditioning and cable TV. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
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Find out more about Windsor Hills

Find out more about Windsor Hills

Why visit Windsor Hills

  1. Proximity to Theme Parks: Windsor Hills is just minutes away from Orlando's famous attractions, making it a prime spot for family fun.
  2. Luxurious Accommodations: Enjoy a range of vacation rentals, from cozy villas to spacious condos, ensuring a comfortable stay.
  3. Outdoor Adventures: The area offers access to serene lakes and golf courses, perfect for relaxation and recreation.
  4. Family-Friendly Atmosphere: Windsor Hills is designed for families, providing a welcoming environment for all ages.
  5. Local Dining Scene: Explore a variety of dining options that cater to different tastes and preferences.

Popular types of accommodation around Windsor Hills

Discover the charm of Windsor Hills through our selection of vacation rentals, including houses, villas, and condos. Whether you're seeking a cozy retreat or a spacious getaway, Windsor Hills Resort offers a variety of options to suit your needs. Our transparent listings ensure you find the perfect vacation rental that provides both savings and peace of mind for your next Canadian adventure.

  • Houses: The top choice for visitors to Windsor Hills, offering spacious accommodations perfect for families or groups.
  • Villas: These elegant and well-appointed properties are the second most sought-after option, ideal for those seeking luxury and comfort.
  • Condos: A popular choice for smaller groups, providing a blend of convenience and amenities in a compact setting.
  • Apartments: A practical option for solo travellers or couples, offering essential comforts and easy access to local attractions.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere for a relaxing getaway.**

Top attractions around Windsor Hills

Windsor Hills is an ideal destination for families seeking outdoor and entertainment-themed adventures. With its proximity to theme parks, golf courses, and serene lakes, there's no shortage of attractions to explore. Whether you're looking for thrilling experiences or relaxing family outings, Windsor Hills provides a perfect blend of fun and recreation for all ages.

  1. Walt Disney World® Resort: Experience the magic at this iconic theme park, featuring thrilling rides, enchanting attractions, and vibrant entertainment suitable for the whole family, located 11.3km from Windsor Hills.
  2. Orange County Convention Center: Immerse yourself in the local culture at this arts centre, hosting various events and exhibitions, just 16.1km away from Windsor Hills.
  3. ChampionsGate Golf Club: Enjoy a family-friendly golf experience at this beautiful course, complete with friendly staff and excursions, located 6.4km from Windsor Hills.

Things to do recommended for couples

For a romantic getaway in Windsor Hills, indulge in a round of mini-golf at Disney's Winter Summerland, only 4.8km away. Enjoy a delightful dinner at Pirate's Dinner Adventure, 19.3km from your stay, or unwind at the luxurious Ridgewood Lakes Golf and Country Club, situated 14.5km away.

Things to do recommended for families

Families visiting Windsor Hills can enjoy the energetic atmosphere at ESPN Wide World of Sports, splash around at Disney's Typhoon Lagoon Water Park, or unwind in the serene surroundings of Northeast Regional Park, all within a short drive from your accommodation.

Things to do recommended for groups

Groups visiting Windsor Hills can enjoy a day at Disney Springs for shopping and dining, explore Old Town for entertainment, or tee off at the nearby Mystic Dunes Golf Club for a fun outdoor experience. Each spot offers a unique vibe for all ages.

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

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—be sure to refine your search based on your key priorities. Here are some valuable Vrbo booking tips to assist you.

  • Traveling to Windsor Hills with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windsor Hills with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor Hills: For many families, a trip isn’t truly fulfilling without their furry companions. If this resonates with you, take a look at Vrbo listings that accommodate pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills: If you're searching for vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking spot, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay around Windsor Hills

Windsor Hills, a delightful family-friendly neighbourhood in Central Florida, offers an exceptional vacation experience. Just minutes away from Orlando's famed attractions, this area boasts luxurious accommodations and a welcoming atmosphere perfect for relaxation and fun. Explore nearby parks, enjoy themed entertainment, and indulge in the local dining scene. Whether you're seeking adventure or a peaceful retreat, Windsor Hills provides an unforgettable getaway for families looking to create lasting memories.

  • Lake Buena Vista: Located 9.7km from Windsor Hills, Lake Buena Vista is a vibrant city known for its family-friendly atmosphere and entertainment options. Visitors flock to this area to experience a mix of business and leisure, with access to luxurious resorts and expansive shopping areas, including bustling shopping malls. The city is also home to iconic landmarks such as theme parks, film studios, and sports stadiums, making it a hub for fun and excitement.
  • Crestwynd Bay: Just 483m from Windsor Hills, Crestwynd Bay is a charming neighbourhood perfect for families and outdoor enthusiasts. This area boasts easy access to resorts and shopping areas, as well as excellent golfing opportunities. Visitors can enjoy the close proximity to major attractions, including theme parks, film studios, and stadiums, ensuring a fun-filled experience for everyone.
  • Indian Ridge: Situated 1.6km from Windsor Hills, Indian Ridge is a delightful neighbourhood ideal for family outings and outdoor adventures. Known for its golfing facilities and welcoming resorts, this area offers a relaxed atmosphere while remaining close to major attractions. Visitors can explore nearby theme parks, film studios, and stadiums, providing a fantastic blend of leisure and entertainment.

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. Peak season runs in January and March to April, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly HighAverage
February64.4°F (18.0°C)Light RainMostly SunnyAverageSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnyAverageSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, feel free to use our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your adventure!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your travel details. You’ll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a vacation rental in Windsor Hills?
Season, property type and length of stay are some of the things that can affect the price of a vacation home. Simply add your travel dates to find your perfect escape. From homey country cottages to expansive villas, all Vrbo vacation rentals 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 vacation rental. Put in your Windsor Hills travel dates to see your options on Vrbo. 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 vacation rental in Windsor Hills?
The minimum age requirements can differ across properties on Vrbo, so check the rules of the vacation home in Windsor Hills you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Windsor Hills for?
The amount of time you can stay in a Windsor Hills vacation rental 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 Vrbo vacation homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.

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