Windwood Bay vacation rentals

We found 59 vacation rentals — enter your dates for availability

Discover a selection of 9 homes and other vacation rentals in Windwood Bay that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you need and want for your stay, which might include WiFi and a pool. No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.

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Find out more about Windwood Bay

Why visit Windwood Bay

  • Proximity to Theme Parks: Windwood Bay is just a short drive from popular attractions like Disney World, making it ideal for family fun.
  • Outdoor Activities: Enjoy serene lakes, golf courses, and recreational activities, perfect for adventure seekers.
  • Charming Neighborhoods: Explore beautiful residential areas that reflect the warmth of Central Florida's community spirit.
  • Diverse Accommodation Options: Choose from private vacation homes, luxurious villas, or cozy condos to suit your needs.
  • Family-Friendly Atmosphere: Windwood Bay offers a welcoming environment, ensuring lasting memories for visitors of all ages.

Popular types of accommodation around Windwood Bay

Planning a getaway to Windwood Bay? The excitement begins with selecting your perfect accommodation. Discover the most sought-after options, including stunning houses, luxurious villas, and cozy condos. Whether you prefer a refreshing dip in an outdoor pool or the privacy of your own pool, Windwood Bay has something for everyone. Explore the Reserve at Windwood Bay for an unforgettable stay.

  • Houses: The top choice for visitors to Windwood Bay, offering spacious accommodations perfect for families, friends, or couples seeking privacy and comfort.
  • Villas: A popular option featuring luxurious amenities and stunning surroundings, ideal for those looking for a more upscale retreat.
  • Condos: These provide a convenient and comfortable stay with easy access to local attractions, perfect for smaller groups.
  • Apartments: A practical choice for travelers seeking affordability and a home-like atmosphere during their visit.
  • Cottages: This charming option offers a cozy and intimate setting, perfect for a romantic getaway or peaceful retreat.**

Top attractions near Windwood Bay

Windwood Bay in Davenport, Florida, is perfect for family-friendly vacations filled with outdoor activities and entertainment. Enjoy thrilling theme parks, serene lakes, and golf courses for a well-rounded experience. You can explore local attractions, relax by the water, play ping pong, or plan a trip to Disney World. With its charming homes and beautiful surroundings, Windwood Bay offers something for everyone looking to create lasting memories.

  • Walt Disney World® Resort: A magical theme park offering immersive experiences, thrilling rides, and beloved characters. It's a perfect destination for families, filled with entertainment options that create unforgettable memories.
  • Orange County Convention Center: A vibrant arts center that hosts various cultural events, exhibitions, and performances. It’s an excellent spot to explore local art and engage with the community's creative spirit.
  • ChampionsGate Golf Club: A family-friendly golf course that offers stunning views and a welcoming atmosphere. Ideal for golfers of all skill levels, it features excursions and activities for everyone.

Things to do recommended for couples

For a romantic getaway near Windwood Bay, consider a round of golf at Ridgewood Lakes Golf and Country Club, just 4 miles away, or indulge in the luxury of Windermere Country Club, located 18 miles away. Both offer a perfect blend of relaxation and elegance for couples.

Things to do recommended for families

Families visiting Windwood Bay can explore the thrilling attractions at nearby Walt Disney World, enjoy a day of fun at Legoland Florida, and relax at the scenic Lake Louisa State Park, perfect for picnics and outdoor activities.

Things to do recommended for groups

Groups visiting Windwood Bay can enjoy a thrilling day at nearby theme parks, indulge in a fun-filled adventure at local escape rooms, or relax with a round of golf at beautiful courses. Don’t miss the chance to explore the nearby scenic lakes and nature trails together.

*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 Windwood Bay

When planning your trip—whether you're traveling with a group, family, pets, or looking for an extended stay—be sure to filter your options according to what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Windwood Bay with a group: Think about how many bedrooms you'll require, along with amenities like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Windwood Bay with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with 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 Windwood Bay: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windwood Bay: If you’re seeking vacation rentals with great deals 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windwood Bay

Windwood Bay, nestled in Davenport, Florida, is a fantastic destination for families seeking outdoor adventures and entertainment. With its friendly atmosphere and proximity to Orlando, visitors can enjoy a variety of excursions, from theme parks to relaxing recreational activities. Explore the charming residential neighborhoods and discover the beauty of Central Florida's homes, all while experiencing the warmth of a community that welcomes tourists with open arms.

  • Orlando: Orlando is a bustling metropolis known for its vibrant entertainment scene and family-friendly attractions. Located a short distance from Windwood Bay, this city is a premier destination for fun seekers. Visitors can explore world-renowned theme parks, including Walt Disney World and Universal Studios, which promise thrilling adventures for all ages. In addition to theme parks, Orlando offers a variety of shopping areas, arts centers, and resorts that cater to both leisure and business travelers. The city boasts local landmarks such as beautiful beaches and dynamic film studios, making it a must-visit for anyone looking for a diverse travel experience.
  • Bridgewater Crossing: Situated just 0.5 miles from Windwood Bay, Bridgewater Crossing is a charming neighborhood that emphasizes outdoor and sports experiences. Travelers flock to this area for its pristine golf courses and recreational parks, perfect for family outings and athletic fun. The neighborhood features lovely resorts that provide relaxation and leisure, making it an ideal spot for a serene escape. Nearby attractions include exciting theme parks and film studios, ensuring that visitors can enjoy both relaxation and adventure during their stay.
  • Loma Linda: Also located 0.5 miles from Windwood Bay, Loma Linda is a welcoming neighborhood that offers a blend of outdoor activities and family-friendly experiences. It is particularly popular among sports enthusiasts, with excellent golf courses and resorts available for visitors. Loma Linda is close to a variety of local attractions, including theme parks and urban parks, offering ample opportunities for exploration and enjoyment. The neighborhood's vibrant atmosphere and commitment to family fun make it a fantastic addition to your Davenport itinerary.

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to 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 vacation rental. We're here to help you find the best options for your needs.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new trips, resume your previous ones, or organize all your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To get started with 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 Windwood Bay?
In Windwood Bay, vacation houses are the most common type of rental, with about 43 available throughout the area. These houses typically offer spacious interiors, multiple bedrooms, and private outdoor spaces, making them ideal for families or groups. Many also feature amenities such as fully equipped kitchens, private pools, and BBQ areas for enjoying meals outdoors. Additionally, several villas, cottages, apartments, and condos are available, providing a variety of options for travelers seeking different styles of accommodation.
Are there any beach house rentals in Windwood Bay?
In Windwood Bay, there are several beach house rentals available, primarily suiting families and groups seeking a spacious getaway. These properties typically feature multiple bedrooms, fully equipped kitchens, and inviting living areas for relaxation. Many beach houses come with outdoor amenities such as private pools, BBQ areas, and patios, making them ideal for enjoying the warm Florida weather. The neighborhood is conveniently located near attractions like the Walt Disney World® Resort and other entertainment options, enhancing the overall vacation experience.
How much does it cost to rent a vacation home in Windwood Bay?
Prices for vacation rentals in Windwood Bay 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 Windwood Bay 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 Windwood Bay vacation house rentals?
You can find great discounts on house rentals in Windwood Bay 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 Windwood Bay?
In Windwood Bay, popular vacation rentals typically feature a variety of desirable amenities that cater to travelers' needs. Most properties come equipped with a fully stocked kitchen, allowing guests to prepare their own meals at their convenience. Many rentals also boast private pools, providing a refreshing retreat right at home. Additional amenities often include coffee and tea makers for a cozy start to the day, as well as decks or patios that offer outdoor spaces for relaxation and enjoying the Florida sunshine. Onsite parking is commonly available, making it easy for guests to explore the surrounding area.
Can I find family house rentals in Windwood Bay?
In Windwood Bay, Florida, there are a number of family-friendly house rentals available, with about 47 options to choose from. This community is conveniently located near popular attractions like Walt Disney World® and other theme parks, making it an excellent choice for families looking to enjoy a vacation filled with fun.

Many of these homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and private pools where kids can splash around. Additionally, travelers can expect amenities such as game rooms for entertainment and outdoor patios great for evening barbecues.
Can I rent a vacation home with a pool or hot tub in Windwood Bay?
In Windwood Bay, Florida, travelers have a great selection of vacation homes available for rent that feature pools and hot tubs, with around 52 properties offering pools and 26 providing hot tubs. This area is known for its family-friendly atmosphere and proximity to attractions like Walt Disney World®, making it an ideal spot for vacationers.

Many of these rentals come equipped with private pools, great for cooling off after a day of exploration, as well as hot tubs for relaxing evenings. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor seating areas, ideal for entertaining or enjoying meals al fresco. Additionally, some homes may offer game rooms, barbecues, and lush gardens, creating a comfortable and enjoyable environment for families or groups.
Are there any Windwood Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windwood Bay 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 book pet-friendly vacation rentals in Windwood Bay?
In Windwood Bay, there are several pet-friendly vacation rentals available, making it a great choice for travelers who wish to bring their furry friends along. This community is known for its spacious homes, often featuring amenities like private pools, fully equipped kitchens, and outdoor spaces superb for relaxation and play. Many rentals provide comfortable living areas and multiple bedrooms, accommodating families or groups.

The area is conveniently located within easy driving distance to several parks and green spaces, which are ideal for walking pets. While Windwood Bay itself has a peaceful suburban feel, it is also close to various attractions in the surrounding areas, ensuring that there are plenty of activities for both you and your pet during your stay.
Can I find long-stay vacation rentals in Windwood Bay?
A long-stay vacation rental in Windwood Bay 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 Windwood Bay for a vacation rental?
The best time to visit Windwood Bay for a vacation rental is during the peak season from July to September. This lively period attracts travelers, drawn to the area's beautiful weather and numerous attractions. With average temperatures ranging from the mid-70s to mid-90s Fahrenheit, visitors can fully enjoy outdoor activities such as swimming, hiking, and exploring nearby theme parks.

July stands out as the most popular month for travelers, offering a bustling atmosphere filled with excitement. Families flock to the various attractions, making it a vibrant time to experience all that Windwood Bay has to offer, from water sports to local dining experiences.

For those who are budget-conscious yet still eager to experience the charm of Windwood Bay, consider visiting in October. This month marks the transition to the low season, providing a more peaceful environment while still enjoying pleasant temperatures and fewer crowds. October is superb for leisurely strolls, enjoying the natural beauty of the area, and taking advantage of potential off-peak rates for vacation rentals.
Are there any remote work vacation rentals in Windwood Bay?
In Windwood Bay, Florida, there are ample options for remote work vacation rentals, with around 52 available properties suiting the needs of digital nomads. Many of these rentals come equipped with essential amenities for working from home, including dedicated workspace features like desks and comfortable chairs. Reliable Wi-Fi is a standard offering, ensuring that guests can stay connected during their stay.

The neighborhood itself is well-situated, providing easy access to local attractions and amenities, such as grocery stores and dining options, making it convenient for longer stays. Additionally, the area is close to popular destinations like Walt Disney World®, offering a superb blend 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 Windwood Bay vacation rental?
Book your Windwood Bay 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 Windwood Bay, Florida, United States of America?
In Windwood Bay, Florida, visitors can enjoy a peaceful retreat while being close to many attractions. The neighborhood is conveniently located near the bustling area of Kissimmee, which offers a variety of entertainment options such as theme parks and shopping centers. Just a short drive away, families can visit Walt Disney World® Resort, including the Magic Kingdom and Epcot, making it an ideal base for those looking to experience the magic of Disney.

Additionally, the nearby Lake Tohopekaliga is great for outdoor enthusiasts, offering opportunities for fishing, boating, and picnicking. For those interested in golf, the area boasts several much-loved golf courses that provide beautiful scenery and challenging play.
Can I change or cancel my Windwood Bay home rental booking on Vrbo?
To find Windwood Bay 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 Windwood Bay 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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