Windsor Hills vacation rentals

We found 2,865 vacation rentals — enter your dates for availability

Select from 1004 houses, 327 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:Dec 12 - Dec 19

Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Living area
9.8 out of 10 rating
Exceptional
(102 reviews)

Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Kissimmee, FL

8% off
Price is $367
$2,569 for 7 nights
All fees included
Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

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Find out more about Windsor Hills

Find out more about Windsor Hills

Why visit Windsor Hills

  • Family-friendly atmosphere: Windsor Hills is ideal for families, offering a vibrant environment with plenty of outdoor activities.
  • Proximity to attractions: Enjoy easy access to popular theme parks and entertainment options in nearby Kissimmee.
  • Diverse accommodations: Choose from a variety of vacation rentals, including private homes, villas, and condos to suit your needs.
  • Outdoor recreation: Experience beautiful lakes and golf courses for both relaxation and adventure.
  • Welcoming community: Interact with friendly locals and enjoy a warm, inviting atmosphere during your stay.

Popular types of accommodation around Windsor Hills

Windsor Hills is a premier vacation rental destination, offering a variety of accommodations to suit every traveler's needs. Whether you prefer a private vacation home, a spacious villa, or a cozy condo, Windsor Hills has something for everyone. With its close proximity to top attractions and family-friendly amenities, Windsor Hills Resort vacation rentals provide the perfect backdrop for your next getaway. Discover your ideal home away from home in Windsor Hills today.

  • Houses: The top choice for visitors in Windsor Hills, offering spacious accommodations perfect for families or groups seeking privacy and comfort.
  • Villas: A popular option for those desiring luxury and amenities, these stylish properties provide a relaxing retreat.
  • Condos: Ideal for travelers wanting modern conveniences and shared amenities, often located near attractions.
  • Apartments: A practical choice for individuals or couples looking for cozy and convenient stays.
  • Cottages: Charming and quaint, these rentals offer a homey atmosphere for a peaceful getaway.**

Top attractions near Windsor Hills

Windsor Hills, located in Four Corners, Florida, is perfect for families seeking outdoor and entertainment-themed vacations. This vibrant area offers exciting attractions such as theme parks, beautiful lakes, and golf courses, ensuring a memorable experience for all visitors. Whether you're looking for thrilling adventures or relaxing family activities, Windsor Hills has something for everyone to enjoy.

  • Walt Disney World® Resort: A magical theme park just 7 miles from Windsor Hills, offering thrilling rides, enchanting shows, and beloved Disney characters, perfect for family fun and unforgettable memories.
  • Orange County Convention Center: Located 10 miles away, this arts center hosts a variety of cultural events, exhibitions, and conventions, showcasing local and international talent in a vibrant atmosphere.
  • ChampionsGate Golf Club: Only 4 miles from Windsor Hills, this family-friendly golf course offers beautiful landscapes, exciting excursions, and a welcoming environment for golfers of all skill levels.

Things to do recommended for couples

For a romantic getaway in Windsor Hills, consider a fun round at Disney's Winter Summerland Miniature Golf, just 3 miles away. Delight in a charming dinner at Pirate's Dinner Adventure, 12 miles away, or indulge in luxury at Ridgewood Lakes Golf and Country Club, 9 miles from your stay.

Things to do recommended for families

During your family vacation in Windsor Hills, explore the ESPN Wide World of Sports Complex for thrilling sports action, cool off at Disney's Typhoon Lagoon Water Park for exciting water fun, and unwind at Northeast Regional Park for some relaxation and wellness activities.

Things to do recommended for groups

Experience the magic of Disney Springs™ for shopping and dining, just 6 miles away, or head to Old Town, 5 miles away, for entertainment and unique shops. For a sporty outing, enjoy a round at Mystic Dunes Golf Club, located only 0.7 miles from Windsor Hills.

*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 traveling with a group, family, pets, or planning to stay for an extended period, it's important to narrow down your options based on your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windsor Hills with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windsor Hills with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private 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, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with food bowls and 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 criteria as well.

Where to stay near Windsor Hills

Windsor Hills in Four Corners, Florida, is the perfect family-friendly getaway, offering comfortable vacation homes near renowned attractions. With its vibrant atmosphere, you'll find plenty of outdoor recreation, friendly locals, and relaxing spots for the whole family. Explore nearby Kissimmee for even more entertainment options, making your stay a delightful blend of relaxation and adventure.

  • Orlando: Orlando is a bustling metropolis known for its family-friendly attractions and entertainment experiences. Situated in close proximity to Windsor Hills, visitors can easily access world-famous theme parks such as Walt Disney World and Universal Studios. The city is also home to vibrant shopping areas and cultural venues like the Orlando Museum of Art. Outdoor enthusiasts can explore nearby parks and nature trails, while those seeking a taste of local nightlife will find plenty of options in this dynamic city.
  • Four Corners: Four Corners is a charming village that offers a delightful escape for families and travelers looking for entertainment and outdoor activities. Located near Windsor Hills, it features various resorts and golf courses, making it an ideal spot for leisure and relaxation. Visitors can enjoy the proximity to major attractions like theme parks and film studios, as well as sporting events at local stadiums. The community’s laid-back atmosphere and friendly vibe make it a perfect base for exploring the surrounding areas.
  • Crestwynd Bay: Crestwynd Bay is a welcoming neighborhood located just 0.3 miles from Windsor Hills, offering a blend of family-friendly experiences and outdoor fun. Travelers can indulge in nearby resorts, shopping areas, and golf courses that cater to all interests. The local attractions include popular theme parks and film studios, as well as access to stadiums for sports enthusiasts. With its close-knit community feel and convenient location, Crestwynd Bay is an excellent choice for a memorable vacation.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageAverage
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? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. Being the organizer certainly has its perks. Become a member of our One Key rewards program to enjoy exclusive savings and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy way to plan your travels, allowing you to start new trips, continue from where you left off, or manage your existing plans. You can view your saved or booked properties organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Windsor Hills?
In Windsor Hills, vacation houses are the predominant choice among travelers, with around 769 available throughout the community. These spacious homes cater well to families and groups, typically featuring multiple bedrooms, fully equipped kitchens, private pools, and outdoor patios for enjoying the warm Florida weather. The neighborhood is conveniently located near popular attractions such as Disney World, making it an ideal base for those looking to explore the theme parks. Additionally, there are approximately 247 condos and 227 villas, which offer a mix of amenities including community pools, fitness centers, and game rooms, providing diverse options for different preferences.
Are there any beach house rentals in Windsor Hills?
In Windsor Hills, Florida, there is a substantial selection of beach house rentals, with approximately 668 available. These properties are typically located within close proximity to popular attractions such as Walt Disney World and other theme parks, providing easy access for families visiting the area. Travelers can expect a range of amenities, including spacious layouts with multiple bedrooms, private pools, fully equipped kitchens, and outdoor areas for relaxation and gatherings. Many rentals also feature game rooms, home theaters, and community amenities like clubhouses, fitness centers, and playgrounds, making Windsor Hills an appealing destination for family vacations.
How much does it cost to rent a vacation home in Windsor Hills?
Prices for vacation rentals in Windsor Hills vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor Hills to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windsor Hills vacation house rentals?
You can find great discounts on house rentals in Windsor Hills on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Windsor Hills?
In Windsor Hills, popular rental amenities cater to families and groups looking for comfort and fun. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare meals and snacks with ease. A significant highlight is the availability of private pools, with many properties offering heated pools for year-round enjoyment. Additionally, shared pool options provide extra space for relaxation and socializing.
Are there any family house rentals in Windsor Hills?
In Windsor Hills, Florida, there is an impressive selection of over 1,100 family-friendly vacation rentals available. This vibrant community is conveniently situated near popular attractions such as Walt Disney World and Universal Studios, making it an ideal base for families visiting the theme parks. Many of these properties come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces that often include private pools and patios, great for relaxation after a day of adventure.

Visitors can expect amenities like game rooms featuring pool tables and gaming consoles, as well as multiple bedrooms to comfortably accommodate larger groups. See all family-friendly rentals in Windsor Hills.
Can I rent a vacation home with a pool or hot tub in Windsor Hills?
In Windsor Hills, Florida, there are plenty of vacation homes available for rent that come equipped with both pools and hot tubs, with around 1,275 options featuring pools and 767 offering hot tubs. This family-friendly community is situated close to the attractions of Orlando, making it a prime choice for travelers seeking fun and relaxation. Many of these properties are spacious, featuring multiple bedrooms and living areas, ideal for families or groups.

Travelers can expect amenities such as private swimming pools, bubbling hot tubs, fully equipped kitchens, and outdoor dining spaces, great for enjoying Florida's sunny weather. Find your rental in Windsor Hills with a pool or a hot tub.
Are there any Windsor Hills vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windsor Hills with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Windsor Hills?
Yes, you can book pet-friendly vacation rentals in Windsor Hills, Florida. This family-friendly community offers a variety of options, with around 99 rentals available that welcome pets. Many of these properties feature amenities such as private pools, fully equipped kitchens, and game rooms, making them ideal for families or groups traveling with pets.

Windsor Hills is conveniently located near attractions like Walt Disney World, providing easy access for guests looking to explore the theme parks. The area also has nearby parks and walking paths where you can enjoy leisurely strolls with your pet.
Can I find long-stay vacation rentals in Windsor Hills?
A long-stay vacation rental in Windsor Hills is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Windsor Hills for a vacation rental?
The best time to visit Windsor Hills for a vacation rental is during the peak season from January to March. This period attracts travelers seeking warmth and sunshine, making it a prime choice for those looking to escape colder climates. With average temperatures ranging from the mid-50s to low 80s Fahrenheit, visitors can comfortably enjoy outdoor activities like golfing, swimming, and exploring nearby theme parks.

January stands out as a particularly popular month, offering a vibrant atmosphere filled with families and groups eager to make the most of their winter getaway. The pleasant weather is great for sightseeing and relaxing by the pool, while the proximity to attractions such as Walt Disney World enhances the appeal.

For those looking for more budget-friendly options, November presents an excellent opportunity. During this quieter month, you can experience a more laid-back atmosphere while still enjoying mild temperatures and local attractions without the crowds.

Regardless of when you choose to visit, Windsor Hills offers a delightful blend of convenience, comfort, and exciting activities that cater to various travel preferences.
Are there any remote work vacation rentals in Windsor Hills?
In Windsor Hills, Florida, travelers seeking remote work vacation rentals will find a substantial selection, with around 1,242 options available. This family-friendly community is located just minutes from the excitement of Walt Disney World, making it a great base for both work and leisure. Many of the rentals are equipped with dedicated office spaces, high-speed Wi-Fi, and comfortable desks, ensuring that remote work can be done efficiently.

Properties often feature amenities such as spacious living areas, fully equipped kitchens, and outdoor patios, providing a relaxing environment after a day of work. The community also includes resort-style amenities like swimming pools, fitness centers, and playgrounds, which can be enjoyed during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Windsor Hills vacation rental?
Book your Windsor Hills vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor Hills?
Windsor Hills, Florida, is ideally situated for those looking to experience the magic of nearby theme parks. The neighborhood is just a short drive from Walt Disney World Resort, making it a prime location for families visiting the parks. Within Windsor Hills itself, travelers can enjoy a range of amenities including a large community pool, water slides, and a clubhouse with a movie theater, which provide plenty of entertainment options outside of the parks.

For those interested in dining and shopping, the nearby Highway 192 corridor features numerous restaurants, shops, and entertainment venues, offering a variety of cuisines and experiences.
Can I change or cancel my Windsor Hills home rental booking on Vrbo?
To find Windsor Hills vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windsor Hills vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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