Windsor Hills vacation rentals

We found 2,812 vacation rentals — enter your dates for availability

Select from 982 houses, 332 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.

Vacation rentals with weekly discounts - Windsor Hills

Showing deals for:Aug 29 - Sep 5
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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: Experience the magic of nearby attractions like Disney World, perfect for family fun.
  2. Family-Friendly Accommodations: Choose from luxurious villas, private homes, and condos tailored for families.
  3. Outdoor Adventures: Enjoy thrilling water slides at Hills Water Park and serene lakes for relaxation.
  4. Golfing Opportunities: Play at local golf courses, catering to all skill levels in a picturesque setting.
  5. Welcoming Community: Experience the friendly atmosphere filled with locals and exciting excursions.

Popular types of accommodation around Windsor Hills

If you're planning a getaway to Windsor Hills, you're in for a treat! This vibrant resort community offers a variety of vacation rentals to suit every traveler's needs. The most popular options include houses, luxurious villas, and comfortable condos. With our selection of Windsor Hills vacation rentals, you'll find the perfect place to unwind and enjoy all the amenities this fantastic resort has to offer.

  • Houses: The top choice for visitors in Windsor Hills, offering spacious and comfortable settings for families and groups.
  • Villas: A popular option featuring luxurious amenities and often private pools, perfect for a relaxing getaway.
  • Condos: A favored accommodation type that combines convenience and comfort, ideal for short or extended stays.
  • Apartments: Great for travelers looking for a home-like atmosphere with essential facilities for an enjoyable stay.
  • Cottages: A charming option providing a cozy retreat, often surrounded by nature and ideal for a peaceful escape.**

Top attractions near Windsor Hills

Windsor Hills is an ideal destination for families seeking entertainment and outdoor adventures. With attractions like theme parks, including Disney World, and local gems like Hills Water Park and golf courses, there's something for everyone. Thrilling slides and serene lakes add to the excitement, ensuring a memorable vacation experience for travelers of all ages. Enjoy the perfect blend of relaxation and fun in this vibrant community!

  1. Walt Disney World® Resort: Experience the magic of this iconic theme park, just 7 miles from Windsor Hills. With thrilling rides, enchanting shows, and beloved characters, it's a perfect destination for families seeking fun and entertainment.
  2. Orange County Convention Center: Located 10 miles away, this vibrant arts center showcases diverse cultural events and exhibitions, making it an ideal spot for those interested in art and creativity.
  3. ChampionsGate Golf Club: Situated 4 miles from Windsor Hills, this family-friendly golf course offers beautiful landscapes, friendly people, and opportunities for excursions, making it a great spot for both novice and seasoned golfers.

Things to do recommended for couples

Experience romance in Windsor Hills! Enjoy a fun round at Disney's Winter Summerland Miniature Golf Course, just 3 miles away. Savor a delightful dinner at Pirate's Dinner Adventure, located 12 miles away, or unwind at the luxurious Ridgewood Lakes Golf and Country Club, only 9 miles from your stay.

Things to do recommended for families

During your stay in Windsor Hills, enjoy a thrilling day at ESPN Wide World of Sports Complex, just 3 miles away. Dive into fun at Disney's Typhoon Lagoon Water Park, 5 miles from your accommodation, or relax at Northeast Regional Park, located 4 miles away, perfect for family wellness.

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

When planning your trip, whether you're traveling with friends, family, bringing your pets, or seeking extended stays, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Windsor Hills with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Windsor Hills with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with having access to 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 vacation isn't truly special without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills: If you're in search of vacation 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. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windsor Hills

Windsor Hills is the perfect family-friendly destination for your vacation, offering a luxurious resort community with private rentals and family homes. Explore nearby attractions that cater to all ages, from thrilling theme parks to relaxing outdoor spaces. Enjoy the warm atmosphere filled with friendly locals and exciting excursions, ensuring a memorable getaway for everyone. Experience the charm and convenience of Windsor Hills, where adventure and relaxation go hand in hand.

  • Lake Buena Vista: Located 6 miles from Windsor Hills, Lake Buena Vista is a vibrant city known for its family-friendly atmosphere and entertainment options. Visitors flock to this area for its impressive resorts and shopping experiences, including a variety of shopping malls. Notably, Lake Buena Vista is home to world-renowned theme parks and film studios, making it an ideal destination for thrill-seekers and movie buffs alike. Don't miss the chance to explore the local stadium, which often hosts exciting events and activities.
  • Crestwynd Bay: Just 0.3 miles from Windsor Hills, Crestwynd Bay is a charming neighborhood perfect for families and outdoor enthusiasts. This area offers a delightful mix of resorts, shopping areas, and golf courses, catering to a range of interests. The proximity to major theme parks and film studios enhances its appeal, providing visitors with endless entertainment. Whether you're looking to relax at a local resort or enjoy a round of golf, Crestwynd Bay has something for everyone.
  • Indian Ridge: Situated 1 mile away from Windsor Hills, Indian Ridge is a welcoming neighborhood that attracts families and outdoor adventurers. With its beautiful resorts and well-maintained golf courses, it is an ideal spot for those looking to unwind or engage in recreational activities. The area’s close proximity to popular theme parks, film studios, and sports facilities ensures that there is always something exciting to do. Indian Ridge combines relaxation and adventure, making it a great addition to your vacation itinerary.

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 a breeze

Are you hoping to cut costs on your upcoming trip? One effective strategy is to be flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash™ on the full booking amount. Being the organizer truly has its benefits! Enroll in our OneKey rewards program to unlock exclusive savings for members and earn OneKeyCash™ on eligible stays. Sign up now and begin accumulating rewards!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels, allowing you to start new trips, pick up where you left off, or keep your plans organized. You can easily find properties you’ve saved or booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards feature, simply 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?
Length of stay, season and property type are some things that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect match. From quaint country cottages to plush villas, all Vrbo vacation rentals offer incredible 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. Click on your Windsor Hills travel dates to view your available options on Vrbo. Can’t live without a private pool? Use the filters to choose the features and amenities you want.
How old do you have to be to rent a vacation rental in Windsor Hills?
The minimum age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Windsor Hills stay before booking your stay.
How long can I rent a vacation rental in Windsor Hills for?
The length of time you can book a vacation rental in Windsor Hills is down to the property. Just enter your preferred dates to see a list of options offering extended stays. With many creature comforts like laundries and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to find somewhere just right to call your home away from home in Windsor Hills.
Does Vrbo offer discounts for vacation homes in Windsor Hills?
In Windsor Hills, you’ll find some great discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a weekend getaway or a much longer stay, we have a host of options that’ll suit your style.

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