Windsor Hills holiday lettings

We found 2,757 holiday rentals — enter your dates for availability

Select from 159 houses, 70 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:29 May - 5 Jun

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

7% off
Price is £2,460
for 7 nights, 1 home
£351 per night
includes taxes & fees
A Perfect Holiday House Waitting U at Windsor Palms Resort close to Disney World

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Windsor Hills

  • Proximity to Theme Parks: Windsor Hills is just minutes away from iconic attractions like Walt Disney World, making it an ideal base for family outings.
  • Family-Friendly Accommodation: Choose from a variety of private homes, villas, and condos tailored for families seeking comfort and fun.
  • Outdoor Activities: Enjoy a plethora of recreational options, including golf courses and swimming pools, perfect for relaxation and play.
  • Welcoming Community: Experience the charm and warmth of friendly locals in this vibrant neighbourhood.
  • Memorable Experiences: Create lasting memories with a mix of relaxation and adventure in the heart of Florida.

Popular types of accommodation around Windsor Hills

If you're contemplating a getaway to Windsor Hills, look no further! Our vacation rentals offer an array of accommodation options, including houses, villas, and condos. Whether you're seeking a relaxing retreat or a fun-filled holiday, Windsor Hills provides the perfect setting. Explore our selection of Windsor Hills rentals and discover the ideal base for your Orlando adventure at the charming Windsor Hills Resort.

  • Houses: The top choice for visitors in Windsor Hills, these homes offer a spacious and comfortable stay, perfect for families or groups.
  • Villas: A close second, villas provide a luxurious experience with ample amenities and private spaces.
  • Condos: These self-contained units are popular among travellers seeking convenience and comfort.
  • Apartments: A practical option for those looking for a home-like atmosphere during their stay.
  • Cottages: Ideal for a quaint and cosy retreat, these charming accommodations provide a unique experience.**

Top attractions near Windsor Hills

Windsor Hills is the perfect destination for a family holiday, offering a delightful mix of entertainment and outdoor activities. Visitors can explore nearby theme parks, golf courses, and amusement parks, ensuring a memorable experience for all ages. With its focus on family-friendly attractions, Windsor Hills provides a wonderful opportunity for enjoyment and relaxation in the heart of Florida.

  • Walt Disney World® Resort: A magical theme park just 4.3km from Windsor Hills, offering enchanting experiences for families with thrilling rides, character meet-and-greets, and vibrant entertainment. It's a place where dreams come true!
  • Orange County Convention Center: Located 6.2km away, this arts centre showcases a rich cultural vibe, hosting various events, exhibitions, and conferences that celebrate the arts, making it a must-visit for culture enthusiasts.
  • ChampionsGate Golf Club: A family-friendly golf course accommodation just 2.5km from Windsor Hills, offering a welcoming atmosphere and exciting excursions for both novice and experienced golfers alike.

Things to do recommended for couples

For a romantic getaway near Windsor Hills, enjoy a round at Disney's Winter Summerland Miniature Golf, only 1.9km away. Indulge in a delightful dinner at Pirate's Dinner Adventure, 7.5km away, or experience luxury at Ridgewood Lakes Golf and Country Club, located 5.6km from your stay.

Things to do recommended for families

During your family vacation in Windsor Hills, explore the thrilling Disney's Blizzard Beach Water Park for adventure, enjoy the energetic atmosphere at ESPN Wide World of Sports Complex, and unwind at Northeast Regional Park for some relaxation amidst nature.

Things to do recommended for groups

Your group can enjoy a delightful day at Disney Springs™, only 3.7km from Windsor Hills, for shopping and dining. Alternatively, visit Old Town, 3.1km away, for entertainment and shopping. For a bit of sport, the Mystic Dunes Golf Club is a mere 435m away.

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

If you’re travelling with a group, with family, bringing along pets, or seeking longer stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor Hills with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for socialising with your group. Thankfully, you can easily refine your search to include all these options and much more on Vrbo.
  • Traveling to Windsor Hills with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as seek out suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can be beneficial.
  • Taking your pets with you to Windsor Hills: For many, a family holiday isn’t truly complete without their furry companion along for the journey. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Windsor Hills: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on long-term rentals. Don't forget to include options 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 an enchanting neighbourhood perfect for family-friendly holidays, offering a plethora of entertainment and outdoor activities. Just minutes away from iconic parks, this area boasts charming family homes and a welcoming atmosphere. Nearby attractions include Hollywood Hills and the glitz of Beverly Hills, ensuring that visitors can enjoy a delightful mix of relaxation and recreation. Experience the warmth of friendly locals and create unforgettable memories in this vibrant region of Florida.

  • Crestwynd Bay: Nestled a mere 186m from Windsor Hills, Crestwynd Bay is a delightful neighbourhood perfect for families seeking entertainment and outdoor adventures. Visitors can enjoy a variety of activities, including access to nearby resorts and shopping areas, as well as scenic golf courses. The area is also in close proximity to major landmarks such as thrilling theme parks, captivating film studios, and exciting stadiums, making it an ideal spot for those looking to immerse themselves in fun and recreation.
  • Lake Buena Vista: Located approximately 3.7km from Windsor Hills, Lake Buena Vista is a vibrant city that caters to families and business travellers alike. Renowned for its entertainment-themed experiences, visitors can indulge in a wealth of activities, from luxurious resorts to expansive shopping mall centres. Local attractions include world-famous theme parks, film studios, and stadiums that promise unforgettable experiences for guests of all ages. The city's blend of leisure and business amenities makes it a fantastic destination for both relaxation and work.
  • Four Corners: Situated just 1.2km from Windsor Hills, Four Corners is a charming village that offers a perfect balance of family fun and outdoor pursuits. The area is well-known for its resorts and golf courses, providing ample opportunities for recreation and relaxation. Visitors can explore nearby attractions such as theme parks, film studios, and stadiums, ensuring a plethora of entertainment options. Four Corners serves as a delightful retreat for those looking to enjoy the sunshine and vibrant atmosphere of Florida.

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 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

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you may find considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new adventures, pick up where you last stopped, or manage your existing arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply 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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