Windsor Hills holiday lettings

We found 2,700 holiday rentals — enter your dates for availability

Select from 170 houses, 63 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:2 Oct - 9 Oct

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Why visit Windsor Hills

  • Family-friendly atmosphere: Windsor Hills offers a welcoming environment perfect for families, ensuring a relaxing getaway.
  • Proximity to attractions: Enjoy easy access to nearby theme parks, including the famous Disney World.
  • Exceptional accommodations: Choose from stunning private vacation homes, villas, and condos tailored for family needs.
  • Resort amenities: Benefit from fantastic facilities, including a clubhouse, expansive swimming pools, and sports courts.
  • Outdoor leisure activities: Engage in various activities, from leisurely strolls to exciting excursions under the warm Floridian sun.

Popular types of accommodation around Windsor Hills

Welcome to Windsor Hills, a delightful neighbourhood in Four Corners, Florida, perfect for your family getaway. Known for its stunning houses, villas, and condos, Windsor Hills offers exceptional resort amenities including a clubhouse, swimming pools, and sports courts. Enjoy the tranquillity of this community while being close to exciting attractions and experiences that ensure a memorable stay for everyone. Discover the ideal vacation rental that caters to your family’s needs in Windsor Hills.

  • Houses: The top choice for visitors, these spacious residences offer a homely atmosphere, ideal for families or groups seeking privacy.
  • Villas: Luxurious and often featuring private pools, villas provide a perfect blend of comfort and elegance for a memorable stay.
  • Condos: Convenient and often centrally located, condos are a popular option for those wanting easy access to amenities and attractions.
  • Apartments: A practical choice for shorter stays, apartments deliver essential comforts in a compact setting.
  • Cottages: Charming and cosy, cottages are perfect for those looking for a quaint retreat amidst the natural beauty of Windsor Hills.**

Top attractions near Windsor Hills

Windsor Hills, located in Four Corners, Florida, offers a delightful array of attractions for families and entertainment enthusiasts alike. Visitors can explore nearby theme parks, enjoy leisure time at the scenic lakes, or indulge in a round of golf at the local country club. With its family-friendly atmosphere and outdoor experiences, Windsor Hills is an ideal destination for a memorable holiday filled with fun and relaxation.

  • Walt Disney World® Resort: A world-renowned theme park offering enchanting attractions, immersive experiences, and magical entertainment suitable for families. Visitors can explore various themed lands and meet beloved characters.
  • ChampionsGate Golf Club: A premier golf destination featuring beautifully designed courses that cater to players of all skill levels. The friendly atmosphere makes it perfect for family outings and excursions.
  • Disney's Lake Buena Vista Golf Course: A scenic golf course nestled within a tranquil setting, providing a family-friendly environment and opportunities for enjoyable rounds of golf amidst lush landscapes.

Things to do recommended for couples

For a romantic getaway in Windsor Hills, enjoy a sunset stroll around the scenic lake, indulge in a couple’s spa day, or have a candlelit dinner at a local restaurant. Don’t forget to explore the nearby parks for a tranquil picnic amidst nature.

Things to do recommended for families

Families visiting Windsor Hills can enjoy a thrilling day at the nearby Walt Disney World Resort, where enchanting attractions await. Additionally, explore the fun-filled water parks, such as Blizzard Beach and Typhoon Lagoon, offering splashes of excitement for children of all ages.

Things to do recommended for groups

Enjoy a thrilling day at the nearby Walt Disney World Resort, where you can explore magical attractions together. Alternatively, unwind with a scenic boat tour on Lake Tohopekaliga, offering stunning views and a chance to spot local wildlife.

*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 travelling with a group, family, pets, or planning an extended stay, be sure to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Windsor Hills with a group: Think about the number of bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for communal gatherings. Thankfully, you can easily filter for all of these options, and many more, on Vrbo.
  • Traveling to Windsor Hills with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable facilities like private swimming pools. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Windsor Hills: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options such as 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, offers an ideal family vacation experience, with its inviting atmosphere and proximity to attractions like Disney World. This charming neighbourhood boasts well-appointed accommodations, expansive pools, and recreational facilities, making it perfect for relaxation and fun. Families can enjoy various activities, from leisurely strolls to exciting excursions, all while soaking in the warm Floridian sunshine. Windsor Hills truly encapsulates the essence of a perfect vacation in Florida.

  • Orlando: Orlando is a vibrant metropolis and the heart of entertainment in Florida, situated just a stone's throw from Windsor Hills. Renowned for its family-friendly attractions, Orlando offers a plethora of experiences ranging from world-famous theme parks to cutting-edge film studios. Visitors can explore the bustling shopping areas and arts centres, while also indulging in the diverse culinary scene. Local landmarks such as Walt Disney World and Universal Studios are must-see attractions that cater to all ages, ensuring memorable adventures.
  • Lake Buena Vista: Located a mere 10km from Windsor Hills, Lake Buena Vista is a city that epitomises the quintessential holiday experience. Known for its family-centric atmosphere and entertainment options, this area boasts a variety of resorts and shopping centres that cater to every taste. The proximity to iconic attractions, including theme parks and a state-of-the-art sports facility, makes it an ideal destination for both leisure and business travellers. Visitors can enjoy an array of dining options and partake in exciting activities within this lively city.
  • Four Corners: Four Corners is a charming village encompassing Windsor Hills and offers a delightful blend of family fun and outdoor experiences. Known for its resort-style living, Four Corners features scenic golf courses that appeal to enthusiasts and casual players alike. Visitors can explore the nearby theme parks and film studios, while also enjoying the outdoor recreational opportunities available in the area. The village provides a relaxed atmosphere, perfect for unwinding after a day of exploration, making it a hidden gem for tourists seeking a balance of excitement and tranquillity.

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 save on your next adventure? Consider being 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, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for organising your travel plans. You can easily create new trips, resume where you last stopped, or review your arrangements. Your saved or booked properties are neatly organised into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Windsor Hills?
Prices for holiday 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 holiday 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.
Are there any Windsor Hills holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Windsor Hills with parking available—perfect for families or travellers 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 holiday rentals in Windsor Hills?
A long-stay holiday rental in Windsor Hills is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Windsor Hills for a holiday rental?
The best time to visit Windsor Hills for a holiday rental is during the peak season, which runs from January to March. This period is particularly popular among families and adventure seekers looking to enjoy the warm Florida weather while exploring the nearby attractions of Disney World and other theme parks. With average temperatures ranging from 15 to 25 degrees Celsius, visitors can comfortably engage in outdoor activities, making it an ideal time for both relaxation and adventure.

January is a standout month, as it marks the beginning of the year with fewer crowds compared to later months. This allows for a more relaxed experience at the parks, with shorter wait times for rides and attractions. Additionally, the pleasant climate makes it great for enjoying leisurely strolls around the community and local shops.

For those looking for a more budget-friendly option, November is a great time to visit. While it may be considered the low season, visitors can still enjoy pleasant weather and fewer tourists. This month is fantastic for exploring the natural beauty of the area, including nearby state parks, without the hustle and bustle of peak tourist traffic.
How early should I book a Windsor Hills holiday rental?
Book your Windsor Hills holiday 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 holiday 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 resort community located near Orlando, making it an ideal base for exploring several attractions. Just a short drive away, visitors can easily access the iconic Walt Disney World® Resort, including Magic Kingdom, Epcot, and Disney's Hollywood Studios. The proximity to these theme parks makes Windsor Hills particularly attractive for families.

Additionally, the area is conveniently located near other attractions such as the exciting Universal Orlando Resort, which features Universal Studios and Islands of Adventure, offering thrilling rides and entertainment. For those looking for a bit of outdoor fun, the nearby Lake Louisa State Park provides opportunities for hiking, fishing, and enjoying the natural beauty of Florida.
Can I change or cancel my Windsor Hills home rental booking on Vrbo?
To find Windsor Hills holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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