Windwood Bay holiday lettings

We found 62 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • 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 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

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, as it falls within the peak season, which runs from July to September. During these months, families flock to this sunny destination to enjoy the warm weather, with temperatures typically ranging from 24 to 33 degrees Celsius. This is an ideal time for outdoor activities, including visits to theme parks, water sports, and leisurely days at the beach.

In July, the atmosphere is vibrant, filled with fellow holidaymakers seeking fun and relaxation. You'll find a range of entertainment options, from thrilling amusement parks to tranquil walks along the shoreline, making it a great choice for those looking to create lasting memories with loved ones.

If you're seeking a more budget-friendly experience, consider visiting in October. This month offers a quieter atmosphere, allowing you to enjoy the area's attractions without the summer crowds. The weather remains pleasantly warm, making it a great time for sightseeing and exploring the natural beauty of Florida.

Ultimately, the best time to book a holiday rental in Windwood Bay depends on your preference for lively summer activities or a more relaxed experience in the shoulder season.
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.
What are the top attractions in Windwood Bay, Florida, United States of America?
Windwood Bay, located in Florida, is a peaceful residential community that offers proximity to several attractions. While the neighbourhood itself is primarily residential, it is conveniently situated near the excitement of the Orlando area, particularly the theme parks. Just a short drive away, visitors can easily access Walt Disney World®, which includes multiple parks like Magic Kingdom and Epcot, making it a prime location for families.

Additionally, the nearby ChampionsGate area features golf courses and resorts, great for those looking to unwind after a day at the parks. The community's location also allows for easy visits to other attractions like Universal Studios and SeaWorld, all of which are just a short drive away.
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 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 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.
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.

More holiday ideas