Windsor Hills vacation rentals

We found 2,796 vacation rentals — enter your dates for availability

Select from 164 houses, 72 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:May 22 - May 29

Image gallery for A Perfect Holiday House Waitting U at Windsor Palms Resort close to Disney World

Mina's vacation house
8.0 out of 10, Very Good, (35 reviews)
Very Good
(35 reviews)

A Perfect Holiday House Waitting U at Windsor Palms Resort close to Disney World

Kissimmee

8% off
Price is $422
$2,955 for 7 nights
All fees included
A Perfect Holiday House Waitting U at Windsor Palms Resort close to Disney World

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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 most popular type of rental, with about 833 available throughout the community. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families and larger groups. Many vacation houses also come with private pools and outdoor patios, superb for enjoying Florida's warm weather. Additionally, condos follow with around 272 options, which often include amenities such as community pools, fitness centers, and proximity to local attractions.
Are there any beach house rentals in Windsor Hills?
In Windsor Hills, there are around 188 beach house vacation rentals available, making it a popular destination for travelers seeking a spacious and comfortable stay. Most of these rentals are located in family-friendly neighborhoods close to attractions like Walt Disney World® and other theme parks. Travelers can expect amenities such as multiple bedrooms, fully equipped kitchens, private pools, and game rooms, suiting families or larger groups. Many properties also include outdoor areas for relaxation and entertaining, enhancing the overall vacation experience.
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, travelers can expect a variety of popular rental amenities that enhance their vacation experience. Most properties feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining in the comfort of their rental. Many rentals also include private pools, providing a refreshing escape from the Florida heat, along with shared pool options for those who enjoy a more communal atmosphere. Onsite parking is commonly available, making it convenient for guests traveling with their own vehicles. Additional amenities often include coffee and tea makers, ensuring guests can start their day with a warm beverage.
Can I find family house rentals in Windsor Hills?
In Windsor Hills, Florida, there are numerous family-friendly house rentals available, with around 1,151 properties to choose from. This vibrant community is particularly popular among families due to its proximity to attractions like Walt Disney World® and Universal Studios. Many of these homes feature spacious living areas, fully equipped kitchens superb for family meals, and private pools to enjoy during the warm Florida days.

Visitors will also benefit from amenities such as game rooms, home theaters, and outdoor patios, making them ideal for relaxation and entertainment after a day of adventures. The neighborhood is designed with families in mind, offering playgrounds, sports courts, and walking paths, ensuring that guests of all ages can find enjoyment right within the community.
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 feature both pools and hot tubs, with around 1,324 options for homes with pools and 793 with hot tubs. This family-friendly resort community is located just a short drive from the attractions of Orlando, making it a popular choice for visitors. Many of these properties come equipped with private pools, providing a ideal setting for relaxation after a day at the nearby theme parks. Additionally, numerous rentals include hot tubs, ideal for unwinding in the evenings.

Travelers can expect a range of amenities in these homes, including spacious living areas, fully equipped kitchens for preparing meals, and access to community facilities such as a clubhouse, fitness center, and playgrounds. Many properties also boast outdoor patios or screened-in areas, enhancing the experience by allowing guests to enjoy the Florida sunshine.
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.
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, eager to enjoy the warm Florida weather and nearby attractions. With average temperatures ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably explore the area's theme parks, engage in outdoor activities, and soak up the sun by the pool.

January is particularly popular, as it offers a refreshing start to the year. Families can take advantage of relatively lower crowd levels compared to the later winter months, making it an ideal time for sightseeing and enjoying the numerous recreational opportunities Windsor Hills has to offer.

For those looking for a more budget-friendly option, consider visiting in November. This month allows travelers to enjoy the pleasant fall weather while avoiding the hustle and bustle of the peak season. You can explore the area at a more leisurely pace and benefit from potentially lower rental rates.
Are there any remote work vacation rentals in Windsor Hills?
In Windsor Hills, Florida, there is a large selection of remote work vacation rentals, with around 1,333 options available. This family-friendly community is known for its proximity to attractions like Walt Disney World® and offers a range of amenities suited for remote workers. Many rentals feature high-speed internet access, dedicated workspaces, and comfortable living areas that allow for a productive work environment.

Travelers can expect properties with full kitchens, laundry facilities, and access to communal amenities such as pools and fitness centers, providing a balance of work and leisure. 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, Florida, United States of America?
Windsor Hills is a popular vacation community located near the attractions of Central Florida, particularly Walt Disney World®. Many visitors are drawn to the area for its proximity to the theme parks, with easy access to the magic of Disney, as well as Universal Studios and SeaWorld, which are just a short drive away.

Within Windsor Hills itself, families can enjoy the resort-style amenities, including a large community pool with a waterslide, a clubhouse with game rooms, and sports courts for basketball and tennis. The neighborhood is also well-suited for outdoor activities, with walking paths and picnic areas available for relaxation.

Nearby, the vibrant town of Celebration offers charming streets, shops, and dining options, while the Kissimmee area provides additional attractions such as Old Town and the beautiful lakes for fishing and boating.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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