Winter Garden vacation rentals

We found 34,225 vacation rentals — enter your dates for availability

Discover a selection of 32 apartments, 35 condos, and other vacation rentals in Winter Garden that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a pool. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Winter Garden

Showing deals for:Mar 27 - Apr 3

Image gallery for Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

Pool
9.8 out of 10, Exceptional, (128 reviews)
Exceptional
(128 reviews)

Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

Kissimmee

8% off
Price is $756
$5,290 for 7 nights
All fees included
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

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Find out more about Winter Garden

Why visit Winter Garden

  • Family-friendly attractions: Winter Garden offers a variety of fun activities for all ages, from theme parks to outdoor adventures.
  • Picturesque neighborhoods: Stroll through charming streets lined with oak trees and beautiful gardens, perfect for leisurely walks.
  • Rich cultural experiences: Engage with local arts and culture through community events and arts centers.
  • Diverse accommodations: Choose from cozy condos, spacious villas, or private vacation homes to suit your stay.
  • Sunny weather: Enjoy plenty of outdoor opportunities and excursions in the warm Florida sun.

Popular types of accommodation in Winter Garden

If you're considering a getaway to Winter Garden, you'll find a variety of appealing accommodations to suit your needs. Our most popular options include houses, spacious villas, and cozy condos. Whether you're looking for house rentals, vacation homes, or townhouses for rent, Winter Garden has an array of choices to ensure a comfortable and memorable stay. Explore the possibilities and find the perfect place to unwind and enjoy your vacation.

  • Houses: The top choice for travelers in Winter Garden, these homes offer a cozy and spacious environment, perfect for families or groups seeking comfort and privacy.
  • Villas: These upscale properties provide a luxurious experience with beautiful amenities, ideal for those wanting a touch of elegance during their stay.
  • Condos: A popular option for visitors, condos offer convenience and access to shared facilities, making them great for short-term rentals.
  • Apartments: Offering a home-like atmosphere, apartments are perfect for travelers looking for a comfortable and budget-friendly stay.
  • Cottages: These charming, quaint spaces provide a unique and picturesque setting for your vacation, ideal for a peaceful retreat.**

Top attractions near Winter Garden

Winter Garden, Florida, is an ideal destination for families and business travelers alike, offering a blend of entertainment and culture. Visitors can enjoy local attractions such as theme parks, golf courses, and arts centers, catering to those seeking outdoor adventures and cultural experiences. Whether you're traveling with family or looking for leisure activities, Winter Garden has something for everyone to explore and enjoy.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park, featuring enchanting rides, beloved characters, and immersive attractions, perfect for families seeking fun and adventure just 10 miles away from Winter Garden.
  • Orange County Convention Center: Dive into a hub of culture at this arts center, hosting various events and exhibitions, showcasing creativity and innovation, located 12 miles from Winter Garden.
  • Universal CityWalk: Enjoy a vibrant outdoor atmosphere at this tourist precinct, offering dining, shopping, and entertainment, making it an ideal family destination just 10 miles away from Winter Garden.

Things to do recommended for couples

For a romantic getaway in Winter Garden, enjoy breathtaking views on The Orlando Eye, savor a meal at Pirate's Dinner Adventure, or unwind at the luxurious Windermere Country Club. These experiences promise unforgettable moments with your partner amidst scenic charm and vibrant vibes.

Things to do recommended for families

Families visiting Winter Garden can splash around at Universal’s Volcano Bay, enjoy sports excitement at the Kia Center, and have a blast at the Carter Family Bowl, a fun arcade adventure zone right in town. These activities guarantee a memorable family vacation experience.

Things to do recommended for groups

Your group can enjoy shopping and entertainment at Flamingo Crossings Town Center, play a round of golf at Disney's Palm Golf Course, and explore the scenic views along the West Orange Trail for a perfect blend of adventure and relaxation in Winter Garden.

*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 in Winter Garden

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to prioritize your search accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Garden with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Garden 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, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter Garden: For many families, a vacation wouldn't be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Winter Garden: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect 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 as well.

Where to stay in and around Winter Garden

Winter Garden, Florida, offers a delightful blend of family-friendly activities and charming neighborhoods. Explore the picturesque country gardens and oak tree-lined streets, perfect for leisurely strolls. With a variety of housing options available, visitors can immerse themselves in the warm, inviting atmosphere. Nearby attractions and excursions provide unforgettable experiences in sunny weather, making Winter Garden an ideal destination for relaxation and family fun.

  • Orlando: Orlando is a vibrant city located 13 miles from Winter Garden, renowned for its family-friendly attractions and entertainment venues. Visitors flock to Orlando for its world-famous theme parks, including Walt Disney World and Universal Studios, along with an array of shopping destinations and arts centers. The city offers a dynamic travel experience, blending business and leisure, with many resorts catering to both tourists and conference-goers. Notable landmarks include thrilling film studios and expansive event spaces, making Orlando a must-visit for anyone looking to immerse themselves in fun and adventure.
  • Ocoee: Situated just 3 miles from Winter Garden, Ocoee is a charming city that combines family entertainment with outdoor activities. This area offers a variety of resorts and shopping centers, providing ample opportunities for leisure and relaxation. Ocoee's close proximity to theme parks and film studios makes it an ideal spot for visitors seeking excitement. The city's welcoming atmosphere and numerous parks ensure that families have a memorable experience, whether exploring the local shopping mall or enjoying outdoor adventures in the beautiful Florida sunshine.
  • Vista del Lago: Vista del Lago is a delightful neighborhood located in the vicinity of Winter Garden, offering a mix of family-friendly activities and urban experiences. This area provides access to resorts, shopping areas, and golf courses, catering to both leisure and recreation. The neighborhood's close proximity to major attractions like theme parks, film studios, and stadiums makes it an appealing destination for tourists. Vista del Lago's community-oriented vibe and variety of entertainment options make it an excellent choice for visitors looking to enjoy the best of Florida living.

Best time to go to Winter Garden

If you're planning a trip to Winter Garden, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January to February and September, while off-peak times, like May, August and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January59.9°F (15.5°C)Light RainMostly SunnySlightly HighAverage
February63.9°F (17.7°C)Light RainMostly SunnySlightly HighSlightly Low
March67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Moderate RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowAverage
September80.2°F (26.8°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.8°F (23.8°C)Light RainMostly SunnySlightly LowSlightly Low
November67.8°F (19.9°C)Light RainMostly SunnyAverageAverage
December63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your entire reservation. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board feature offers you a convenient way to plan your journeys. You can create new trips, pick up right where you left off, or easily manage and organize your travel plans. Any properties you've saved or booked in the past can now be accessed under Potential, Upcoming, or Current Trips. To explore Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The friendly area of Winter Garden awaits your stay

Experience the unique character of Winter Garden with a stay in a vacation home rental. Well-liked for its theme park, shopping and water park, this city is both welcoming and relaxing. Walt Disney World® area and Walt Disney World® Resort are just a couple of the must-sees. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

West Orange history and wild rides in Winter Garden

Quaint little Winter Garden has its own clutch of intriguing attractions. There's the Winter Garden Heritage Foundation, which chronicles the rich culture of West Orange. There's the Central Florida Railroad Museum with its old tracks and platforms. There's the Garden Theatre, dating back to the 1930s. Winter Garden vacation rentals close to Walt Disney World offer a whole other bunch of delights. Rollercoasters and rides aplenty can be expected, from the sloshing wave pools of Typhoon Lagoon to the dusty savannahs of the wild Animal Kingdom and beyond.

Living like a local in Winter Garden

Walk your way around the old Downtown of Winter Garden to spy out the historic relics of its railroad past – you can even get guided tours of the place to really delve into the heritage. Then, make for the weekly farmer's market to shop for fresh fruit and Floridian produce in the company of locals, or hop between the independent cafes and microbreweries learning the ins and outs of bean roasting and beer tasting. When evening comes, the whole of Plant Street buzzes with life, whether that means summertime jazz sessions or fine-dining in the bistros there.

Exploring the natural features in Winter Garden

Whether you're an active traveler or just want to spend some time taking in the scenery, Winter Garden is a great spot to appreciate mother nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Hancock Park (7.9 mi / 12.7 km)
  • Bill Frederick Park (8 mi / 12.9 km)
  • Rock Springs Run (8.8 mi / 14.2 km)
  • Lake Louisa State Park (11.1 mi / 17.9 km)
  • Wekiwa Springs State Park (12.5 mi / 20.1 km)
  • Lake Eola Park (13 mi / 20.9 km)

Transportation to and around Winter Garden

The nearest airport is in Orlando Intl. Airport (MCO), located 19.3 mi (31 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is 20.8 mi (33.5 km) away.

Frequently asked questions

What is the best area to stay in Winter Garden when booking a vacation rental?
When looking for the best area to stay in Winter Garden, Florida, consider the charming Historic Downtown district. This vibrant area is known for its picturesque streets lined with boutiques, cafes, and restaurants that showcase the town's rich history. Staying in this neighborhood places you within walking distance of popular attractions like the Winter Garden Heritage Museum, where you can delve into the local history, and the scenic West Orange Trail, great for biking or walking while enjoying the natural beauty of the region.

Another excellent option is the nearby Horizon West area, which offers a more suburban feel with modern amenities. This neighborhood is known for its family-friendly atmosphere and proximity to the popular theme parks, making it an ideal choice for those looking to explore attractions like Walt Disney World Resort. Horizon West also features a variety of vacation rental properties, providing ample options for visitors.

Overall, both Historic Downtown and Horizon West boast numerous vacation rental properties, suiting different preferences and group sizes.
How much does it cost to rent a vacation home in Winter Garden?
Prices for vacation rentals in Winter Garden 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 Winter Garden 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 Winter Garden vacation house rentals?
You can find great discounts on house rentals in Winter Garden 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 is the most popular type of vacation rental accomodation in Winter Garden?
In Winter Garden, condos are the most popular type of vacation rental, with about 76 available throughout the charming downtown area and near the West Orange Trail. These condos typically feature modern amenities such as fully equipped kitchens, open living spaces, and access to community facilities like pools and fitness centers.

Apartments also see significant interest, with around 71 options available, often located close to local parks and shopping areas. These rentals generally come with similar amenities, including kitchens and comfortable living areas, making them ideal for both short and extended stays.

For those seeking more space, approximately 48 vacation houses are available, which usually offer multiple bedrooms, private yards, and sometimes even pools—great for families or larger groups. While cottages are less common, with about 10 options, they provide a quaint and cozy alternative for travelers looking for a more rustic experience. Additionally, there are several villas that cater to those wanting a more luxurious stay.
Are there any family house rentals in Winter Garden?
In Winter Garden, Florida, families will find a wealth of options with around 146 rentals available. This charming area is known for its picturesque downtown, where visitors can enjoy local shops, cafes, and parks. Many properties in Winter Garden come equipped with spacious living rooms, full kitchens ideal for family meals, and outdoor areas featuring private pools or patios—superb for gatherings and relaxation.

For families looking for activities, the nearby West Orange Trail offers miles of scenic paths for walking or biking, while the local parks provide playgrounds and picnic spots. Additionally, attractions like the historic Garden Theatre and the vibrant Plant Street Market are just a short drive away, ensuring that families have plenty of entertainment options during their stay. See all family-friendly rentals in Winter Garden.
Can I rent a vacation home with a pool or hot tub in Winter Garden?
In Winter Garden, there are plenty of vacation homes available for rent that come with pools or hot tubs, with around 146 options to choose from. This charming city, known for its picturesque downtown and proximity to Orlando's attractions, features neighborhoods like the historic downtown area and the more suburban communities surrounding the West Orange Trail.

Travelers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for barbecuing or lounging in the sun. Many homes also offer fully equipped kitchens, comfortable living spaces, and family-friendly amenities, making them ideal for both relaxation and entertaining. Find your rental in Winter Garden with a pool or a hot tub.
Can I find long-stay vacation rentals in Winter Garden?
A long-stay vacation rental in Winter Garden 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.
Are there pet-friendly house rentals in Winter Garden?
In Winter Garden, travelers will find a variety of pet-friendly house rentals available, with over a hundred options to choose from. Many of these homes come equipped with spacious backyards, allowing pets to enjoy the outdoors. Amenities often include modern kitchens, comfortable living spaces, and sometimes even private pools, making them ideal for families or groups traveling with pets.

The charming downtown area of Winter Garden features a vibrant atmosphere with local shops, cafes, and restaurants that welcome pets, ideal for travelers. Additionally, nearby parks such as Newton Park and the West Orange Trail provide excellent opportunities for walks and outdoor activities with pets, ensuring that both guests and their furry companions can enjoy their stay. See all pet-friendly rentals in Winter Garden.
Are there any remote work vacation rentals in Winter Garden?
In Winter Garden, Florida, there are numerous vacation rentals suitable for remote work, with around 180 options available. This charming town, known for its historic downtown and proximity to nature, provides a variety of properties equipped with essential amenities for a productive stay. Travelers can expect features such as high-speed Wi-Fi, dedicated desk spaces, comfortable desk chairs, and even business centers in some rentals, ensuring a conducive work environment.

Many properties also offer additional comforts like fully equipped kitchens, outdoor spaces, and community amenities such as pools and fitness centers, allowing guests to balance work and leisure effectively. The nearby West Orange Trail offers scenic paths for walking or biking, while the vibrant downtown area features cafes and shops superb for breaks or after-work relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Garden vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Garden 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.
What are popular rental amenities in Winter Garden?
In Winter Garden, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals during their stay. Additionally, many rentals offer WiFi to keep guests connected, as well as access to shared pools for relaxation and recreation. Some properties even feature private pools for a more exclusive experience. Travelers can also expect conveniences like coffee makers, great for starting each day with a fresh brew.
When is the best time to visit Winter Garden for a vacation rental?
September is one of the most popular months to visit Winter Garden, Florida, as the summer heat begins to wane, making outdoor activities more enjoyable. The peak season typically runs from January to March, drawing visitors who appreciate the warm and sunny weather during those winter months. During this time, you can enjoy a variety of activities such as exploring the scenic West Orange Trail or enjoying the lush landscapes of the local parks.

With average temperatures in the low 70s to mid-80s Fahrenheit, September offers a comfortable climate for sightseeing, dining al fresco, and participating in local events. Visitors can take advantage of the vibrant atmosphere, including farmers' markets and outdoor festivals that showcase the charm of this historic town.

For those seeking a more budget-friendly experience, consider planning your visit in October. This month is less crowded and provides an excellent opportunity to enjoy the beautiful fall foliage in the area. With mild temperatures and fewer tourists, October is great for leisurely strolls through the gardens or enjoying a peaceful day by Lake Apopka.

Ultimately, the best time to visit Winter Garden depends on your preferences for weather, activities, and overall atmosphere.
How early should I book a Winter Garden vacation rental?
Book your Winter Garden 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 Winter Garden?
In Winter Garden, visitors can explore the charming downtown area, known for its historic buildings, boutique shops, and vibrant farmers market held every Saturday. The West Orange Trail, which runs through the city, offers scenic paths for walking, biking, and enjoying the outdoors. Nearby, the beautiful Lake Apopka provides opportunities for birdwatching and fishing, while the Winter Garden Heritage Museum showcases the area's rich history. For family-friendly fun, the Plant Street Market features local vendors and food options, making it a great spot to relax and enjoy the local culture.
Can I change or cancel my Winter Garden home rental booking on Vrbo?
To find Winter Garden 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 Winter Garden 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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