Windwood Bay holiday lettings

We found 72 holiday rentals — enter your dates for availability

Discover a selection of 70 homes, 22 villas and holiday rentals in Windwood Bay that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Windwood Bay

  • Proximity to Disney World: Enjoy easy access to the world-famous Disney World, ensuring excitement for the whole family.
  • Outdoor Activities: Engage in various outdoor pursuits, from scenic lakeside strolls to thrilling golf courses.
  • Family-Friendly Atmosphere: Windwood Bay provides a welcoming environment perfect for families and friends seeking fun.
  • Diverse Accommodation Options: Choose from luxurious villas, private holiday homes, and stylish condos tailored to your needs.
  • Cultural Experiences: Immerse yourself in local culture through sports and recreational activities available in the area.

Popular types of accommodation around Windwood Bay

If you're planning a getaway to Windwood Bay, the next exciting step is selecting your ideal accommodation. Discover the most sought-after options, including houses, luxurious villas, and stylish condos. Whether you're looking for a spacious bedroom villa or a charming retreat, Windwood Bay has something to suit every traveller's needs. Explore the variety of vacation rentals available and make your stay truly memorable.

  • Houses: The top choice for holidaymakers in Windwood Bay, offering spacious and comfortable stays for families or groups.
  • Villas: A popular option for those seeking luxury and style, providing ample space and amenities for a relaxing getaway.
  • Condos: Favoured by many, these offer a blend of comfort and convenience, often located near attractions.
  • Apartments: A practical choice for visitors wanting a home-like atmosphere with easy access to local amenities.
  • Cottages: Charming and cosy, these quaint retreats provide a lovely escape for couples or small families.**

Top attractions near Windwood Bay

Windwood Bay in Davenport, Florida, is perfect for families and outdoor enthusiasts seeking a variety of activities. The area boasts popular attractions such as theme parks, scenic lakes, and golf courses, making it an ideal destination for those wanting to enjoy sports and cultural experiences. Whether you're travelling with family or friends, Windwood Bay offers plenty of opportunities for adventure and relaxation in a beautiful setting.

  • Walt Disney World® Resort: A magical theme park brimming with entertainment and family-friendly attractions, located 7.5km from Windwood Bay. Experience enchanting rides, character meet-and-greets, and immersive themed lands that create unforgettable memories.
  • Orange County Convention Center: This vibrant arts centre lies 9.3km away and showcases a variety of cultural events, exhibitions, and performances, making it a hub of creativity and artistic expression.
  • ChampionsGate Golf Club: Located just 1.2km from Windwood Bay, this welcoming golf course offers family-friendly excursions, friendly people, and a great atmosphere for both seasoned players and beginners alike.

Things to do recommended for couples

For a romantic getaway in Windwood Bay, enjoy a round of golf at Ridgewood Lakes Golf and Country Club, indulge in fun at Disney's Winter Summerland Miniature Golf Course, or savour delightful wines at True Blue Winery. Each offers a unique, intimate experience for couples.

Things to do recommended for families

During your family vacation in Windwood Bay, enjoy thrilling adventures at Disney's Typhoon Lagoon Water Park, unwind at Northeast Regional Park, or experience the excitement of sports at the ESPN Wide World of Sports Complex, all within a short drive from your accommodation.

Things to do recommended for groups

Groups visiting Windwood Bay can enjoy a delightful day at Disney Springs™ for shopping and dining, explore the vibrant atmosphere of Old Town, and unwind with a round of golf at the picturesque Mystic Dunes Golf Club, all within a short drive from your accommodation.

What do I need to keep in mind when booking a vacation around Windwood Bay

If you're travelling with a group, family, pets, or seeking extended stays, it's important to tailor your search according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windwood Bay with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windwood Bay with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise 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 Windwood Bay: For many families, a holiday just wouldn’t be the same without their beloved pet. If you can relate, take a look at Vrbo properties that welcome furry companions. Most of these pet-friendly accommodations 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 in search of holiday rentals offering 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 accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Windwood Bay

Windwood Bay, nestled in Davenport, Florida, offers a delightful family-friendly atmosphere perfect for a memorable holiday. Explore the nearby attractions, including the world-renowned Disney World, where excitement awaits around every corner. Engaging outdoor activities and recreational opportunities abound in the area, ensuring fun for all ages. Whether you're seeking relaxation or adventure, Windwood Bay and its surrounding regions promise an unforgettable family vacation experience.

  • Bridgewater Crossing: Bridgewater Crossing is a delightful neighbourhood situated half a mile from Windwood Bay. This area attracts visitors with its emphasis on outdoor activities, sports, and family-friendly experiences. Guests can enjoy a variety of venues, including resorts and golf courses, perfect for both relaxation and recreation. Nearby, you'll find significant attractions such as a prominent theme park, a film studio, and a convention centre, offering ample opportunities for entertainment and adventure.
  • Loma Linda: Located half 1.6km away from Windwood Bay, Loma Linda is another charming neighbourhood that prioritises outdoor enjoyment, sports, and family activities. The area boasts an inviting atmosphere with excellent access to resorts and golf courses, making it a popular choice for those looking to unwind or stay active. Attractions in the vicinity include a renowned theme park, a film studio, and a venue for events and conferences, ensuring a diverse range of activities for all visitors.
  • Champions Gate: Situated one mile from Windwood Bay, Champions Gate is a vibrant area that attracts travellers seeking outdoor adventures, sports, and family experiences. Visitors can take advantage of its resorts and golf courses, providing ample options for leisure. Additionally, the neighbourhood is close to notable landmarks, including a theme park, a film studio, and even a beach, making it an ideal destination for those looking to explore and enjoy Florida’s attractions.

Booking with Vrbo is a breeze

Are you hoping to keep costs down on your next getaway? It might be worthwhile to maintain some flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often allows for significant savings. To discover the perfect Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or keep your travel plans organised. Here, you can easily access the properties you’ve saved or booked, neatly sorted into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Windwood Bay?
In Windwood Bay, holiday houses are the most popular type of rental, with around 51 available throughout the area. These spacious homes are ideal for families or groups, offering multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or patios for relaxing after a day of exploring. Additionally, there are about 10 villas, which provide a more luxurious experience with upscale amenities and often private pools. There are also several cottages and apartments, which offer a cozier atmosphere for couples or smaller groups.
Are there any beach house rentals in Windwood Bay?
In Windwood Bay, Florida, there are several beach house rentals available, primarily featuring spacious layouts suitable for families or groups. These properties typically include multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or balconies, superb for enjoying the warm Florida weather. The area is conveniently located near attractions like Disney World and local shopping areas, making it an excellent base for those looking to explore the broader Orlando region.
How much does it cost to rent a holiday home in Windwood Bay?
Prices for holiday 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 holiday 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.
Are there any Windwood Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Windwood Bay 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 Windwood Bay?
A long-stay holiday rental in Windwood Bay 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 Windwood Bay for a holiday rental?
July is the most popular time to visit Windwood Bay, Florida, attracting families and sun-seekers eager to enjoy the vibrant atmosphere of summer. This peak season, extending from July to September, is characterised by warm temperatures, typically in the high 30s Celsius. Visitors can bask in the sunshine, explore nearby theme parks, or relax by the pool in their holiday rental.

During this bustling period, you'll find an abundance of activities tailored for all ages, from thrilling adventures at Walt Disney World to leisurely days at local beaches. The lively environment fosters a sense of community, great for families looking to create unforgettable memories together.

If you're seeking a more budget-friendly option, consider planning your visit in October. This month offers a fantastic opportunity to enjoy pleasant weather while avoiding the summer crowds. With temperatures still comfortably warm, you can relish outdoor activities such as hiking or cycling without the hustle and bustle of peak season.
Are there any remote work holiday rentals in Windwood Bay?
In Windwood Bay, Florida, there are numerous options for remote work holiday rentals, with around 60 available in the area. This charming neighbourhood is situated conveniently close to various attractions, including theme parks and shopping centres, making it an ideal base for both work and leisure.

Travellers can expect properties equipped with essential remote work amenities such as high-speed WiFi, dedicated desk spaces, and comfortable office chairs. Many rentals also feature additional conveniences like laptop workstations and ample natural light, creating a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Windwood Bay holiday rental?
Book your Windwood Bay 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.
Can I change or cancel my Windwood Bay home rental booking on Vrbo?
To find Windwood Bay 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windwood Bay 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.

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