Windsor Hills Resort vacation rentals

We found 1,123 vacation rentals — enter your dates for availability

Holiday rentals with weekly discounts - Windsor Hills Resort

Showing deals for:Dec 11 - Dec 18

Image gallery for Stay in this wonderful home just 3 miles from Disney World!

Windsor Hills Zero Entry Pool
9.8 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Stay in this wonderful home just 3 miles from Disney World!

Kissimmee

5% off
Price is CA $493
CA $4,604 total
includes taxes & fees
Stay in this wonderful home just 3 miles from Disney World!

Find spaces that suit your style

Find out more about Windsor Hills Resort

Why visit Windsor Hills Resort

  • Proximity to Theme Parks: Windsor Hills Resort is just a short drive from popular attractions like Disney, making it an ideal base for family adventures.
  • Family-Friendly Atmosphere: The resort fosters a welcoming environment, perfect for families seeking a fun and relaxing holiday experience.
  • Diverse Recreational Activities: Enjoy a mix of outdoor activities, from sunny pool days to nearby golf courses and serene lakes.
  • Variety of Accommodations: Choose from spacious villas and cozy condos to suit your family's needs and preferences.
  • Memorable Excursions: Explore the vibrant local area, filled with attractions and experiences for all ages.

Popular types of accommodation around Windsor Hills Resort

Planning a getaway to Windsor Hills Resort? You're in for a treat. Discover a variety of popular accommodations, including family homes, spacious villas, and cozy condos. Whether you’re seeking a magical holiday home for the whole family or looking to relax in one of the best rental communities, Windsor Hills offers something for every traveller. Enjoy transparency, savings, and peace of mind as you choose the perfect holiday home for your next adventure.

  • Private Holiday Homes: Ideal for families or groups, these spacious homes offer the comforts of home with added privacy and amenities.
  • Villas: Luxurious and often featuring private pools, villas provide a lavish getaway experience with ample space and style.
  • Condos: Perfect for couples or small families, condos combine convenience with modern living, often located near attractions.
  • Apartments: Offering a comfortable stay, apartments are great for those seeking a home-like atmosphere during their visit.
  • Cottages: Cozy and charming, cottages provide a quaint and peaceful retreat, ideal for relaxing after a day of adventures.**

Top attractions near Windsor Hills Resort

Windsor Hills Resort and its surrounding areas offer a delightful mix of attractions, perfect for families and outdoor enthusiasts alike. Visitors can enjoy thrilling theme parks, serene lakes, and beautiful golf courses, ensuring a memorable experience filled with entertainment and recreation. Whether you're seeking adventure or relaxation, there's something for everyone to explore in this vibrant locale.

  • Walt Disney World® Resort: This iconic theme park is a magical destination filled with thrilling rides, enchanting shows, and beloved characters, perfect for families looking to create unforgettable memories. Located 11km from Windsor Hills Resort, it offers a variety of attractions for visitors of all ages.
  • ChampionsGate Golf Club: Just 6km away, this family-friendly golf course features beautifully designed fairways and a welcoming atmosphere, making it an excellent spot for both seasoned players and newcomers seeking a fun day on the links.
  • Disney's Lake Buena Vista Golf Course: Situated 10km from Windsor Hills Resort, this charming golf course offers a picturesque setting with friendly staff and a relaxed vibe, ideal for families looking to enjoy a leisurely round of golf together.

Things to do recommended for couples

For a romantic getaway near Windsor Hills Resort, enjoy a sunset stroll at Lake Louisa State Park, or indulge in a couples' spa day at a nearby wellness centre. Don't miss a candlelit dinner at a charming local restaurant to make your holiday truly special.

Things to do recommended for families

Your family can enjoy a delightful day at the nearby Disney World, where magic awaits at every corner. Explore the fun attractions at Legoland Florida, perfect for young adventurers, and cool off at the water parks for a refreshing experience after a long day of excitement.

Things to do recommended for groups

Groups staying at Windsor Hills Resort can enjoy a day at nearby Disney World, explore the vibrant shops and restaurants at Disney Springs, or take a scenic stroll in the picturesque Lake Louisa State Park, perfect for picnics and nature walks.

*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 Resort

When planning your trip, whether you're traveling with a group, family, or pets, or if you're seeking longer stays, be sure to prioritize your preferences in the search filters. Here are some helpful booking tips for Vrbo.

  • Traveling to Windsor Hills Resort with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Windsor Hills Resort with young kids: Traveling with young children can be quite the adventure. It’s important to prioritize their comfort and safety, along with ensuring 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 Resort: For many families, a trip isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills Resort: If you're in search of holiday rentals with special offers 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windsor Hills Resort

Windsor Hills Resort serves as a perfect base for a family holiday in Florida, offering an inviting atmosphere with friendly people and plenty of recreational activities. Just a few km from Disney, this family-friendly destination allows travellers to explore nearby attractions, enjoy relaxing excursions, and create unforgettable memories. With its ideal location, visitors can experience the best of both relaxation and adventure in the heart of the Sunshine State.

  • Lake Buena Vista: Located 10km from Windsor Hills Resort, Lake Buena Vista is a vibrant city that offers a family-friendly atmosphere and a plethora of entertainment options. Visitors can enjoy extensive shopping areas and malls, making it perfect for a day of retail therapy. The area is renowned for its proximity to iconic theme parks and film studios, providing endless excitement for families and thrill-seekers alike. With a variety of dining and recreational facilities, Lake Buena Vista is a delightful destination for both leisure and business travelers.
  • Crestwynd Bay: Situated a mere 483m from Windsor Hills Resort, Crestwynd Bay is a charming neighborhood that caters to families and business visitors alike. This community is home to shopping areas and an arts centre, making it a great spot to explore local culture and creativity. With popular attractions such as theme parks and sports facilities nearby, Crestwynd Bay offers a dynamic blend of activities. Whether you're looking for a fun day out or a quiet retreat, this neighborhood is perfect for a quick excursion.
  • Indian Ridge: Just 2km away from Windsor Hills Resort, Indian Ridge is a picturesque neighborhood that emphasizes family fun and sports activities. With stunning golf courses and recreational facilities easily accessible, this area is ideal for those looking to enjoy the outdoors. Visitors can also take advantage of its close proximity to theme parks and film studios, ensuring a fulfilling day of exploration. Indian Ridge is a great choice for anyone seeking a balance of leisure and adventure during their holiday.

Best time to go to Windsor Hills Resort

If you're planning a trip to Windsor Hills Resort, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November 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 SunnyAverageSlightly Low
February64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
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 SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnySlightly LowSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowAverage
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save some cash on your upcoming adventure? Being flexible with your travel dates can really pay off, as prices tend to vary. Additionally, if you opt for a longer stay, you may enjoy significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental. We've got your back to ensure you find the best deal.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or manage your itinerary with ease. You can easily access properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Windsor Hills Resort?
The best vacation rentals near Windsor Hills Resort are predominantly located within the Windsor Hills area itself, offering convenient access. You will find a vast selection of properties, mainly consisting of private vacation houses and spacious villas. These options provide ample room and privacy, making them a popular choice for guests. For those seeking the best vacation rentals near Windsor Hills Resort, staying within this immediate vicinity offers the most convenience.

Many of these properties boast excellent amenities such as private pools, shared community pools, and fitness facilities, ensuring a comfortable and enjoyable stay. These types of homes are ideal for families or large groups looking for a relaxing and amenity-rich holiday.
Are there any cheap vacation rentals near Windsor Hills Resort?
There are several affordable vacation rentals near Windsor Hills Resort, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around CA $215 per night in areas like Windsor Hills. Some stays even offer good deals in September and October during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy private vacation houses to modest villas, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Windsor Hills Resort while keeping costs down, so you can have a comfortable stay.

*Pricing data are based on past 12 months data.
What are the best pet-friendly vacation rentals near Windsor Hills Resort?
There are numerous pet-friendly vacation rentals available near Windsor Hills Resort, with over 1,800 properties welcoming pets. These include a large selection of private vacation houses and villas in the Four Corners area, offering essential amenities such as kitchens, Wi-Fi, and comfortable living spaces. Many properties also provide specific pet-friendly features like dog exercise areas and food and water bowls, ensuring a pleasant stay for both guests and their furry companions.

When searching for the best pet-friendly vacation rentals near Windsor Hills Resort, always review the specific house rules regarding pet types, size restrictions, and any additional fees. While Windsor Hills Resort itself has designated areas where pets are allowed, such as paved paths within the community, for more extensive outdoor activities, nearby public parks like Lake Louisa State Park offer ample space for pets to roam and explore.
What are the top vacation rentals with pools near Windsor Hills Resort?
There are nearly 10,000 vacation rentals near Windsor Hills Resort that include access to swimming pools, offering both private and shared options. Properties in the Windsor Hills area primarily consist of private vacation houses and villas, many featuring outdoor pools, heated pools, and even children's pools. These homes often come fully equipped with amenities such as full kitchens, Wi-Fi, and multiple bedrooms, making them ideal for families or larger groups looking for a comfortable stay.

When selecting your ideal rental, consider the benefits of each pool type. Private pools provide seclusion and are excellent for families seeking personal space, while shared pools, often part of a community complex, might include additional facilities like waterslides or poolside bars. For cooler months, look for heated or indoor pool options to ensure year-round enjoyment.
What are the best family vacation rentals near Windsor Hills Resort?
There are over 8,262 family-friendly holiday homes in the vicinity of Windsor Hills Resort, predominantly private vacation houses and villas, offering ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, full kitchens for preparing meals, and washer/dryers for laundry convenience. Many also boast outdoor play areas like private yards or gardens, and some even include playgrounds or water parks, ensuring entertainment for all ages. WiFi and video games are commonly available for downtime.

When selecting your ideal family vacation rental, consider properties that provide separate spaces for adults and children to relax, and prioritise those with practical amenities such as a well-equipped kitchen. Staying close to Windsor Hills Resort means less travel time and more opportunities to enjoy the facilities.
Are there any luxury vacation rentals near Windsor Hills Resort?
Near Windsor Hills Resort, guests can find several luxury vacation rentals that combine a family-friendly atmosphere with upscale comfort. These properties often feature amenities such as private heated pools, private outdoor hot tubs, deep soaking bathtubs, and premium bedding. Some homes even offer additional luxuries like private chefs, designer toiletries, and private plunge pools.

These stays are ideal for families or larger groups, offering conveniences like air conditioning and entertainment spaces. Many of these exceptional properties are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Windsor Hills Resort?
Vacation rentals near Windsor Hills Resort offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around CA $215 per night, providing an affordable option. Mid-range rentals, including private homes with standard amenities, are generally around CA $340 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost CA $485 or more per night, especially for properties with extensive amenities or premium locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Windsor Hills Resort?
When planning a stay near Windsor Hills Resort, several nearby areas offer excellent options for vacation rentals. The immediate Windsor Hills area itself is highly sought after, featuring a variety of properties that are either within the resort's gated community or just a stone's throw away. This proximity provides convenient access to all the amenities and attractions associated with Windsor Hills Resort.

Another excellent option is the Formosa Gardens area. This neighbourhood offers spacious homes and is renowned for its beautiful, larger properties, many with private pools. Staying here provides a luxurious base and is a short drive from Windsor Hills Resort, making it easy to enjoy both the resort and other local entertainment.

Kissimmee is also a popular choice, particularly for those looking for a diverse range of vacation rentals and easy access to a wider selection of dining and shopping. Properties in Kissimmee are well-situated for visiting Windsor Hills Resort and other major attractions in the region.
What is the cheapest month to stay near Windsor Hills Resort?
The cheapest time to find vacation rentals near Windsor Hills Resort is typically during the Autumn (September to October), excluding any major local holidays. September is frequently the cheapest month, often providing the best deals on homes and properties, with rates often 15-25% lower compared to peak season. Guests can often find various savings during these months, along with greater availability of vacation rentals.
Are there any lakefront vacation rentals near Windsor Hills Resort
Lakefront vacation rentals near Windsor Hills Resort are available, primarily found on the many beautiful lakes within the Four Corners area. These properties are a short drive from Windsor Hills Resort, offering convenient access to water activities such as kayaking, fishing, or relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the peaceful surroundings and natural beauty.
Are there any monthly vacation rentals near Windsor Hills Resort?
Vrbo offers excellent options for monthly vacation rentals near Windsor Hills Resort, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Windsor Hills Resort.
Are there any last-minute vacation rentals near Windsor Hills Resort?
Vrbo makes it simple to find last-minute vacation rentals near Windsor Hills Resort that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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.

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 favourites, and build the perfect itinerary together.

More Vacation Ideas