Windsor Hills Resort vacation rentals

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Vacation rentals with weekly discounts - Windsor Hills Resort

Showing deals for:May 15 - May 22

Image gallery for South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney

Lovely pool area
9.8 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)

South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney

Kissimmee

7% off
Price is $634
$4,440 for 7 nights
All fees included
South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney

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Find out more about Windsor Hills Resort

Why visit Windsor Hills Resort

  • Proximity to Theme Parks: Enjoy easy access to world-renowned attractions like Disney World and Universal Studios, perfect for family fun.
  • Family-Friendly Accommodations: Choose from a variety of vacation rentals, including spacious homes and cozy villas tailored for families.
  • Relaxing Amenities: Unwind by the resort's pools, hot tubs, and recreational facilities designed for all ages.
  • Outdoor Activities: Explore nearby lakes and golf courses for outdoor adventures and leisure time.
  • Charming Neighborhood: Experience the inviting community of Kissimmee, with its shops, dining, and friendly atmosphere.

Popular types of accommodation around Windsor Hills Resort

Planning a getaway to Windsor Hills Resort? You've made a fantastic choice. Explore our selection of popular vacation rentals, including private homes, villas, and condos that offer the perfect blend of comfort and convenience. Whether you’re seeking a cozy retreat or a spacious family-friendly accommodation, Windsor Hills has something for everyone. Discover the best Windsor Hills Resort rentals to make your vacation unforgettable.

  • Houses: The top choice for visitors to Windsor Hills Resort, offering spacious and comfortable accommodations perfect for families or groups.
  • Villas: A favored option, these luxurious rentals provide a blend of comfort and elegance, ideal for a relaxing getaway.
  • Condos: A popular choice for travelers seeking convenience and amenities, perfect for smaller groups or couples.
  • Apartments: An affordable and practical option, ideal for those who want to enjoy a home-like atmosphere during their stay.
  • Cottages: A cozy and charming retreat, perfect for a quaint and intimate vacation experience.**

Top attractions near Windsor Hills Resort

Windsor Hills Resort offers a variety of attractions perfect for families and outdoor enthusiasts. Nearby, you'll find thrilling theme parks, serene lakes for relaxation, and top-notch golf courses for a fun day on the greens. Whether you're seeking entertainment or adventure, there's something for everyone to enjoy during your stay in this vibrant area of Four Corners, Florida.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park, just 7 miles from Windsor Hills Resort. With enchanting attractions, character meet-and-greets, and spectacular shows, it’s a must-visit for families seeking unforgettable entertainment.
  • Orange County Convention Center: Located 10 miles away, this vibrant arts center hosts various cultural events and exhibitions, offering a glimpse into the local and international art scene. Enjoy a day of creativity and inspiration.
  • ChampionsGate Golf Club: Only 4 miles from Windsor Hills, this family-friendly golf course features exceptional amenities, scenic views, and a welcoming atmosphere, perfect for casual players and seasoned golfers looking for a fun outing.

Things to do recommended for couples

For a romantic getaway near Windsor Hills Resort, enjoy a round of mini-golf at Disney's Winter Summerland, just 3 miles away. Indulge in a delightful dinner at Pirate's Dinner Adventure, 12 miles away, or relax at the luxurious Ridgewood Lakes Golf and Country Club, only 9 miles from your stay.

Things to do recommended for families

Your family will have a blast at ESPN Wide World of Sports Complex, only 3 miles away, for sports excitement. Enjoy thrilling water rides at Disney's Typhoon Lagoon Water Park, 5 miles away, or unwind at Northeast Regional Park, located 4 miles away, perfect for relaxation and wellness.

Things to do recommended for groups

Explore Disney Springs™ for shopping and dining just 6 miles from Windsor Hills Resort, or visit Old Town for entertainment, only 5 miles away. For sports enthusiasts, Mystic Dunes Golf Club is a fantastic outdoor option, located a mere 0.7 miles from your accommodations.

*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

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windsor Hills Resort with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Windsor Hills Resort with young kids: Traveling with young kids can be tough. 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 Resort: For many families, a getaway isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Windsor Hills Resort: If you're searching for vacation rentals that offer 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windsor Hills Resort

Windsor Hills Resort in Four Corners, Florida, offers an unforgettable vacation experience filled with family-friendly attractions and warm hospitality. Explore nearby Kissimmee, known for its charming vacation homes and ample recreational facilities. Stroll along the inviting sidewalks, relax by the pool, or embark on exciting excursions to theme parks. With a perfect blend of relaxation and adventure, this destination is ideal for families looking to make lasting memories together.

  • Orlando: Orlando is a vibrant metropolis known for its family-friendly attractions and entertainment theme parks. Located just a short drive from Windsor Hills Resort, it offers a plethora of activities for visitors of all ages. Experience the magic of renowned theme parks like Walt Disney World and Universal Studios, where adventure awaits. Beyond the parks, indulge in shopping at famous outlets, explore the arts at local centers, and unwind at beautiful resorts. With its diverse dining options and lively nightlife, Orlando ensures an unforgettable vacation experience.
  • Four Corners: Four Corners is a charming village that perfectly complements the excitement of nearby attractions. Situated near Windsor Hills, it’s an ideal spot for families seeking outdoor fun and entertainment. Golf enthusiasts can take advantage of the various golf courses available in the area, while the proximity to theme parks and stadiums ensures plenty of activities. Enjoy the relaxed atmosphere, explore local dining options, and experience the community spirit of this friendly village, making it a delightful addition to your travel itinerary.
  • Windsor Hills: Windsor Hills is a welcoming neighborhood that boasts a resort-style atmosphere, making it a popular destination for families. The resort features amenities such as pools, sports facilities, and shopping areas, all within easy reach. As part of the greater Orlando area, Windsor Hills offers quick access to world-class theme parks and entertainment venues. Enjoy outdoor activities, relax in beautiful surroundings, and create lasting memories with loved ones in this family-oriented community that perfectly combines relaxation and adventure.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
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 SunnyAverageSlightly 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 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 LowSlightly Low
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 simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and rental type. We're here to help you find the perfect getaway.

Unlock savings with One Key

Make your group trip even more rewarding by booking an eligible Vrbo and earning OneKeyCash on your entire reservation. Being the planner truly has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is designed to help you plan your travel effortlessly. You can start new trips, refine your existing plans, or easily manage your bookings all in one place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, and Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/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 directly within the Windsor Hills neighborhood in Four Corners, Florida. You will find a great selection of properties, with many private vacation homes and villas available. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as private pools for refreshing dips, shared pools, and fitness facilities. These homes are ideal for families or multiple groups wanting to enjoy the area's attractions.
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 $160 per night. Some stays even drop below this price 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 cozy private vacation homes 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.
What are the best pet-friendly vacation rentals near Windsor Hills Resort?
There are over 100 pet-friendly vacation rentals available near Windsor Hills Resort. These properties, primarily private homes and villas in the Four Corners area, often feature amenities like fenced yards, private decks, and easy outdoor access, alongside essential comforts such as fully equipped kitchens and Wi-Fi. Guests will find a comfortable and convenient stay for both themselves and their animal companions.

For those seeking the best pet-friendly vacation rentals near Windsor Hills Resort, remember to review each property's specific house rules, including any size restrictions or additional fees for pets.
What are the top vacation rentals with pools near Windsor Hills Resort?
There are over 9900 vacation rentals near Windsor Hills Resort that include access to swimming pools, with both private and shared outdoor options available, many of which are heated for guest comfort. These properties are primarily concentrated within the Windsor Hills neighborhood itself. Many of these homes come fully equipped with amenities such as full kitchens, multiple bedrooms, Wi-Fi, and sun loungers by the pool, making them ideal for families or groups looking for a comfortable stay near the resort.

To make the most of your stay, consider the type of pool that best fits your needs. Private pools offer seclusion and are great for families, while shared pools often come with access to additional perks like children's pools or resort-inclusive facilities. Many pools are heated, so checking availability based on your travel dates ensures you get the experience you seek, especially during cooler months.
What are the best family vacation rentals near Windsor Hills Resort?
There are over 8,200 family-friendly vacation homes available near Windsor Hills Resort, predominantly private vacation homes and villas, offering extensive space and comfort for groups of all sizes. These properties often feature multiple bedrooms and bathrooms, full kitchens for meal preparation, and washer/dryers, which are essential for families. Many also provide outdoor play areas like yards or patios, and entertainment options such as video games and arcade rooms, ensuring a fun and convenient stay for everyone.

When selecting the ideal property for your family, look for homes that offer separate living spaces for adults and children, and prioritize practical amenities like a fully equipped kitchen to simplify meal times and laundry facilities to manage clothes. Staying close to Windsor Hills Resort reduces travel time, allowing your family more opportunity to enjoy the attractions.
Are there any luxury vacation rentals near Windsor Hills Resort?
Near Windsor Hills Resort, there are several luxury vacation rentals that combine elegant surroundings with modern comfort. These properties often feature amenities such as private hot tubs, deep soaking bathtubs, private pools, and premium bedding. Some homes even offer golf course views or private chefs.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and access to resort amenities. Many of these top-tier stays 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 typically start around $160 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around $250 per night, offering more comfort and privacy. Upscale options can cost $355 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.
Where should I stay when visiting Windsor Hills Resort?
When visiting Windsor Hills Resort, you have excellent options for vacation rentals that enhance your stay. The immediate Windsor Hills neighborhood offers properties directly within or very close to Windsor Hills Resort, providing the utmost convenience for enjoying the resort's amenities and proximity to major attractions. These rentals often feature private pools and spacious layouts, superb for families and larger groups.

Just a short drive away, the wider Four Corners area provides a fantastic selection of homes. This region is known for its diverse range of vacation rentals, many of which are situated in communities with their own recreational facilities, offering additional leisure opportunities. Guests often appreciate the easy access to various dining and shopping options in this area.
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 season (September to October). September is often the single cheapest month, frequently offering the best deals on homes and condos, with rates often 15-25% lower compared to peak season. Guests can usually find lower rates and better availability during these months.
Are there any lakefront vacation rentals near Windsor Hills Resort
Lakefront vacation rentals near Windsor Hills Resort are available, providing a wonderful blend of comfort and water-based recreation. Many properties are found along the numerous lakes and waterways throughout the Four Corners area. These properties are a short drive from Windsor Hills Resort, offering convenient access to water activities such as kayaking, fishing, boating, and swimming, or simply 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 lake views and direct water access from many of these properties.
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 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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