Windwood Bay vacation rentals

We found 77 vacation rentals — enter your dates for availability

Discover a selection of 70 homes, 24 villas, and 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.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Windwood Bay

Find out more about Windwood Bay

Why visit Windwood Bay

  1. Outdoor adventures: Windwood Bay offers plenty of opportunities for hiking, fishing, and exploring scenic lakes and parks.
  2. Proximity to theme parks: Located near Orlando, visitors can easily access world-famous attractions like Disney World and Universal Studios.
  3. Family-friendly neighborhoods: Discover charming local communities perfect for family outings and activities.
  4. Diverse accommodation options: Choose from spacious vacation homes, cozy condos, or stylish apart-hotels to suit your needs.
  5. Relaxing beach access: Enjoy the stunning Southside beaches for a day of sun and relaxation.

Popular types of accommodation around Windwood Bay

Explore the charm of Windwood Bay with our selection of vacation rentals! From spacious houses to modern apart hotels and cozy condos, there’s something for everyone. Whether you're looking for a serene getaway at Windwood Bay Villas or the convenience of The Reserve at Windwood Bay, you'll find the perfect spot for your stay in Davenport. Discover the ideal vacation rental in Windwood Bay that suits your needs and enhances your travel experience.

  • Houses: The top choice for travelers in Windwood Bay, offering spacious and comfortable accommodations suitable for families or groups.
  • Condos: A favored option for those seeking convenience and amenities, ideal for couples or small families.
  • Apartments: Popular among solo travelers and couples, providing a cozy and affordable stay.
  • Villas: A luxurious choice, perfect for larger gatherings, featuring upscale amenities and privacy.
  • Cottages: Charming and quaint, ideal for a romantic getaway or a peaceful retreat.**

Top attractions around Windwood Bay

Windwood Bay in Davenport, Florida, is perfect for outdoor enthusiasts and families seeking adventure. Visitors can explore popular attractions like theme parks, scenic lakes, and urban parks that provide a blend of fun and cultural experiences. Whether you're looking for a day of excitement or a relaxing outing, Windwood Bay has something for everyone to enjoy.

  1. Walt Disney World® Resort: A magical theme park just 11 miles from Windwood Bay, featuring iconic attractions, character meet-and-greets, and enchanting experiences for the entire family. Enjoy thrilling rides, spectacular shows, and a variety of dining options in a whimsical setting.
  2. Universal Studios Florida: Located 18 miles away, this film studio-themed park immerses you in the world of movies, offering exhilarating rides based on popular films and interactive experiences that are perfect for families.
  3. Orange County Convention Center: Just 15 miles from Windwood Bay, this arts center hosts a variety of cultural events, exhibitions, and conventions, showcasing local talent and providing a taste of the vibrant arts scene in Central Florida.

Things to do recommended for couples

Experience romance in Davenport, Florida! Take a ride on The Wheel at ICON Park™ for stunning views, challenge each other at Disney's Winter Summerland Miniature Golf Course, or enjoy a luxurious day at Ridgewood Lakes Golf and Country Club. Perfect for memorable couple adventures!

Things to do recommended for families

Your family will have a blast at ESPN Wide World of Sports, only 7 miles from Windwood Bay, engage in thrilling water adventures at Disney's Blizzard Beach Water Park, also 7 miles away, or unwind at Northeast Regional Park, just 6 miles away, perfect for relaxation and wellness.

Things to do recommended for groups

Groups visiting Windwood Bay can enjoy shopping and dining at Disney Springs™ or Old Town, both offering vibrant atmospheres. For outdoor enthusiasts, the nearby ChampionsGate Golf Club provides a perfect spot for a fun day on the greens, just minutes away from your accommodations.

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

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

  • Traveling to Windwood Bay with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windwood Bay 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 swimming pool. Additionally, 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 fulfilled without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Windwood Bay: If you're in search of vacation rentals that offer special rates for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria for an even better experience.

Where to stay around Windwood Bay

Windwood Bay in Davenport, Florida, is the perfect base for an unforgettable vacation. Explore the vibrant atmosphere of nearby Orlando, with its world-famous attractions, or discover the charm of Davenport's family-friendly neighborhoods. Enjoy outdoor adventures in Central Florida or relax on the stunning Southside beaches. With its mix of sports, family activities, and romantic excursions, you’ll find plenty to create lasting memories in this beautiful region.

  • Orlando: Located 24 miles from Windwood Bay, Orlando is a vibrant city known for its family-friendly atmosphere and entertainment options. Visitors flock to this bustling metropolis for its world-renowned theme parks, including Walt Disney World and Universal Studios. Beyond the attractions, Orlando offers a diverse range of shopping areas, from luxury malls to quaint boutiques. The arts scene thrives here, with venues such as the Dr. Phillips Center for the Performing Arts hosting concerts and theatrical performances. With its blend of excitement and culture, Orlando is an essential stop for any vacationer in the area.
  • Kissimmee: Just 12 miles from Windwood Bay, Kissimmee is a charming city that caters to families and thrill-seekers alike. This lively destination is famous for its proximity to major theme parks and is a hub for outdoor activities. Visitors can enjoy shopping at local malls and resorts that offer a range of amenities. Kissimmee also boasts beautiful lakes and parks, perfect for a leisurely stroll or a picnic. With its inviting atmosphere and numerous attractions, Kissimmee is a fantastic place to experience the magic of Central Florida.
  • Bridgewater Crossing: Only half a mile from Windwood Bay, Bridgewater Crossing is a peaceful neighborhood perfect for outdoor enthusiasts and families. This idyllic area features stunning golf courses and resorts that provide a relaxing atmosphere for visitors. The neighborhood is conveniently located near popular attractions, including theme parks and event venues, making it an ideal base for exploring the region. With its focus on sports and outdoor activities, Bridgewater Crossing offers a serene getaway while still being close to the excitement of nearby attractions.

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. It truly pays off to take on the planning role! By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn as well as use OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, continue from where you last left off, or manage your existing plans all in one place. Your saved or booked properties will be organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Windwood Bay?
The most sought-after types of vacation rentals in Windwood Bay are villas. Looking for something different? Vrbo has numerous options to match our guests’ needs, so you’ll see properties in all sizes and shapes. The ideal fit is ready and waiting for you — find yours today.
How much does it cost to rent a vacation rental in Windwood Bay?
Season, property type and length of stay are among the factors that can affect the price of a vacation home. Simply click on your travel dates to find your perfect match. From cozy chalets to sprawling luxury villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Windwood Bay?
The average price for a vacation rental close to the beach in Windwood Bay will depend on when you’re going and the type and size of property you’re searching for. Find prices easily on Vrbo by entering the dates you’ll be traveling. Then use our filters to select the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.
Are there pet-friendly vacation rentals in Windwood Bay?
Pack a tug toy and treats for your pooch because Windwood Bay has 58 vacation homes that throw out the welcome mat to doggie guests. Let your four-legged buddy enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Windwood Bay?
Pack your swimming gear and swim ring, because there are 57 houses with a private pool in Windwood Bay. Base yourself at one of these superb vacation rentals and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place to make a splash!
What are popular rental amenities in Windwood Bay?
The most popular rental amenities people search for in Windwood Bay include an electric car charging station, a fireplace and a nearby river. Whether you’re going on vacation with family, your besties or even pets, Vrbo vacation properties come with the best amenities for making epic memories with the people that matter most.
Are there large group vacation rentals in Windwood Bay?
With 30 properties that can sleep 10 guests or more in Windwood Bay, you won’t have to keep anyone off the invite list. From family vacations to events like anniversary parties and weddings, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Windwood Bay that welcome kids?
Gather your whole crew for an unforgettable adventure in Windwood Bay at one of our 58 family-friendly vacation properties. These stays come with conveniences that are just perfect for getaways with the little ones, including full kitchens, living rooms and pools. Simply check the “Properties good for families” filter box and choose your favorite option.
Are there vacation rentals with WiFi in Windwood Bay?
You can pick from 23 vacation rentals with WiFi in Windwood Bay. If you want to disconnect from the world during your escape, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Windwood Bay?
Work out your travel dates and then make use of our filters to find vacation rentals with ac in Windwood Bay on Vrbo. With 57 air-conditioned properties to choose from here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a vacation rental in Windwood Bay?
The minimum required age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Windwood Bay vacation home before making a booking.
How long can I rent a vacation rental in Windwood Bay for?
How long you can rent a vacation rental in Windwood Bay varies according to the property. Simply enter your chosen dates to see a list of options offering extended stays. With many features like laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to get a terrific place to call your home away from home in Windwood Bay.
Does Vrbo offer discounts for vacation homes in Windwood Bay?
In Windwood Bay, you’ll find some fabulous bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re off on a short getaway or an extended stay, we have a variety of options to suit every kind of traveler.

More Vacation Rentals ideas