Winter Garden holiday homes

We found 34,129 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Winter Garden that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Winter Garden

Showing deals for:5 Feb - 12 Feb

Image gallery for Super Fun House with Amazing Views

Interior
10 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)

Super Fun House with Amazing Views

Kissimmee

8% off
Price is NZ$29,741
for 7 nights, 1 home
NZ$4,249 per night
includes taxes & fees
Super Fun House with Amazing Views

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Why visit Winter Garden

  • Charming historic centre: Stroll through Winter Garden’s quaint streets, soaking up the old-world charm and community spirit.
  • Family-friendly parks: Enjoy lush urban parks perfect for picnics, leisurely walks, and outdoor fun.
  • Recreational golf: Tee off at local country clubs offering a relaxing day on the greens.
  • Sunny outdoor adventures: Embrace the warm weather with a mix of leisure and active pursuits.
  • Cultural and community events: Experience local festivities that highlight Winter Garden's vibrant atmosphere.

Top attractions near Winter Garden

Winter Garden, Florida, offers a delightful mix of family-friendly attractions and outdoor experiences. You can explore its charming urban parks, enjoy a round of golf at local country clubs, or immerse yourself in the excitement of nearby theme parks. This vibrant city caters to a variety of interests, making it an ideal destination for family holidays, entertainment seekers, and culture enthusiasts alike. Discover the unique charm and activities that Winter Garden has to offer during your visit.

  • Walt Disney World® Resort: A magical theme park offering thrilling rides, beloved characters, and immersive entertainment perfect for families and visitors of all ages.
  • Universal CityWalk: A vibrant tourist precinct featuring an array of shops, restaurants, and entertainment options, ideal for outdoor enjoyment and family fun.
  • Arnold Palmer's Bay Hill Golf Club: A prestigious golf course and country club known for its scenic beauty and welcoming atmosphere, perfect for golf enthusiasts seeking adventure.

Things to do recommended for couples

Winter Garden offers charming experiences for couples, such as a leisurely stroll along the West Orange Trail, a delightful boat ride on Lake Apopka, or a romantic dinner at a local bistro. Don't forget to catch a sunset at the beautiful downtown park for a perfect end to your day.

Things to do recommended for families

Families will love exploring the lush trails of the West Orange Trail, discovering the interactive exhibits at the Orlando Science Center, and enjoying the vibrant atmosphere of the Winter Garden Farmers Market on weekends. These experiences offer a delightful taste of local life and fun for all ages.

Things to do recommended for groups

Groups visiting Winter Garden can enjoy a scenic stroll along the West Orange Trail, explore the charming shops and eateries in the historic downtown, or take a relaxing boat tour on Lake Apopka to soak in the area's natural beauty and wildlife.

*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 travelling with a group, with family, bringing your pets, or seeking extended stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Garden with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can easily refine your search to include these options and more on Vrbo.
  • Traveling to Winter Garden with young kids: Traveling with little ones can be a challenge. It’s important to prioritise their comfort and safety, along with ensuring access to age-suitable features like a private pool. It’s also wise to consider your closeness to attractions that are family-friendly.
  • Taking your pets with you to Winter Garden: For many, a family holiday simply isn’t complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that all members of the family feel right at home.
  • Planning for a long term stay visiting Winter Garden: 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winter Garden

Winter Garden invites visitors to explore its charming streets, vibrant family-friendly atmosphere, and a relaxing blend of city and town warmth. Enjoy a leisurely stroll along its historic centre, bask in sunny weather, and discover local attractions that offer a taste of true community spirit, perfect for a memorable holiday experience in this delightful Florida city.

  • Orlando: Located 21km from Winter Garden, Orlando is a vibrant city known for its family-friendly attractions and entertainment theme parks. Visitors flock to this bustling metropolis for its dynamic blend of leisure and business opportunities. The area is home to iconic theme parks, world-class arts centres, and extensive shopping areas. Orlando's local landmarks, including renowned film studios and event conference venues, make it a hub for both tourists and business travellers alike. Whether you're seeking thrilling rides or cultural experiences, Orlando offers a plethora of options to suit all interests.
  • Ocoee: Situated a mere 5km from Winter Garden, Ocoee is a charming city that invites families and outdoor enthusiasts to explore its offerings. Known for its friendly atmosphere, Ocoee features numerous shopping centres and recreational spaces. The city's proximity to theme parks and sports facilities provides ample entertainment options, making it an ideal spot for those looking to combine relaxation with adventure. Enjoy the local parks and enjoy the outdoor activities that Ocoee has to offer, ensuring a memorable experience for visitors of all ages.
  • Vista del Lago: Nestled around Winter Garden, Vista del Lago is a delightful neighbourhood that caters to families and those seeking a city-themed experience. This area boasts an array of shopping areas and malls, perfect for retail therapy. With its close proximity to picturesque lakes and popular theme parks, Vista del Lago offers a unique blend of leisure and excitement. Visitors can explore local attractions, enjoy scenic views, and take part in various outdoor activities that showcase the charm of this inviting community.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January59.9°F (15.5°C)Light RainMostly SunnySlightly High
February63.9°F (17.7°C)Light RainMostly SunnySlightly High
March67.3°F (19.6°C)Light RainMostly SunnyAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverage
May77.2°F (25.1°C)Light RainMostly SunnySlightly Low
June81.0°F (27.2°C)Moderate RainMostly SunnyAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverage
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly Low
September80.2°F (26.8°C)Moderate RainMostly SunnySlightly High
October74.8°F (23.8°C)Light RainMostly SunnySlightly Low
November67.8°F (19.9°C)Light RainMostly SunnyAverage
December63.7°F (17.6°C)Light RainMostly SunnyAverage

Booking with Vrbo is simple

Are you keen to stretch your travel budget further? Try keeping your travel dates flexible, as rates can vary. Moreover, booking for a longer period often leads to significant savings. To discover the ideal Vrbo accommodation that fits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use space where you can start new trips, resume where you left off, or organise your plans. You’ll see properties you’ve saved or booked grouped into Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The friendly area of Winter Garden awaits your stay

Learn about the unique charm of Winter Garden with a stay in a holiday home rental. Revered for its theme park, shopping and water park, this city is both welcoming and relaxing. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winter Garden

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winter Garden a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (9.3 mi / 14.9 km)
  • Universal Orlando Resort (9.6 mi / 15.5 km)
  • Magic Kingdom® Park (10.2 mi / 16.4 km)
  • Walt Disney World® Resort (10.3 mi / 16.6 km)
  • Epcot® (13.6 mi / 21.8 km)
  • Disney's Animal Kingdom® Theme Park (14.2 mi / 22.9 km)

Exploring the natural features in Winter Garden

Whether you're looking for adventure or just want to spend some time taking in the scenery, Winter Garden is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Bill Frederick Park (8 mi / 12.9 km)
  • Lake Louisa State Park (11.1 mi / 17.9 km)
  • Lake Eola (13 mi / 20.9 km)
  • Lake Eola Park (13.2 mi / 21.2 km)
  • Little Lake Bryan (13.9 mi / 22.4 km)
  • Harry P. Leu Gardens (13.9 mi / 22.4 km)

Transport to and around Winter Garden

The nearest airport is in Orlando International Airport (MCO), located 19.3 mi (31 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to 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 holiday rental?
When considering a holiday rental in Winter Garden, Florida, a popular area to stay is the historic downtown district. This charming neighbourhood boasts a delightful blend of old-world charm and modern amenities, making it a popular choice for visitors. You'll find an array of lovely properties ranging from quaint bungalows to more contemporary homes, allowing for a variety of options to suit different tastes and budgets.

In downtown Winter Garden, you'll have access to the West Orange Trail, a beautiful path ideal for walking, cycling, and enjoying the local scenery. Additionally, the area is home to the Winter Garden Theatre, which offers a cultural experience with its engaging performances and events. The vibrant local farmers' market on weekends is also a must-visit, showcasing fresh produce and artisanal goods.

Another great option is the nearby Horizon West neighbourhood, known for its family-friendly atmosphere and newer developments. This area features a range of holiday rentals and is conveniently located close to popular attractions like the Walt Disney World® Resort, making it an excellent choice for those looking to explore the theme parks.
What is the most popular type of holiday rental accomodation in Winter Garden?
In Winter Garden, condos are the most popular type of holiday rental, with approximately 276 available across the area. These condos are often situated in well-maintained communities, close to attractions such as the historic downtown area and the West Orange Trail. Most units come equipped with modern amenities, including fully fitted kitchens, open-plan living spaces, and access to communal facilities like swimming pools and fitness centres.

Apart from condos, there are about 104 apartments available, providing a more compact alternative that still offers essential conveniences. For those seeking additional space, around 96 holiday houses can be found, featuring multiple bedrooms, private gardens, and outdoor dining areas—ideal for families or larger groups. There are also about 40 cottages and 40 villas, which provide a unique charm and often include amenities like fireplaces and scenic views.
Are there any family house rentals in Winter Garden?
In Winter Garden, Florida, there are numerous family-friendly house rentals available, with around 98 options to choose from. This charming area is known for its proximity to popular attractions such as Walt Disney World® and the picturesque Winter Garden Village, making it an excellent choice for family holidays.

Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor patios or backyards where children can play safely. Visitors can also expect amenities like Wi-Fi, laundry facilities, and sometimes even private pools, ensuring a comfortable stay for families of all sizes.

Additionally, the local community features parks, playgrounds, and scenic walking trails, great for family outings.
Can I rent a holiday home with a pool or hot tub in Winter Garden?
In Winter Garden, there are plenty of holiday homes available for rent that feature pools or hot tubs, with around 93 options to choose from. This charming area, located near the scenic Lake Apopka, offers a mix of family-friendly neighbourhoods and beautiful surroundings.

Travellers can expect a variety of amenities in these rentals, including private pools, relaxing hot tubs, spacious outdoor areas, and fully equipped kitchens, superb for entertaining or enjoying meals al fresco. Many properties are designed to provide comfort and convenience, often featuring air conditioning, Wi-Fi, and entertaining spaces, making them ideal for families or groups looking to unwind after exploring the local attractions. Find your rental in Winter Garden with a pool or a hot tub.
Are there pet-friendly house rentals in Winter Garden?
In Winter Garden, there is a good selection of pet-friendly house rentals available, with approximately 67 options to choose from. Many of these properties come equipped with modern amenities such as spacious living areas, fully equipped kitchens, private outdoor spaces, and sometimes even pools, making them comfortable for both you and your furry companions.

The neighbourhoods within Winter Garden offer a charming mix of suburban comfort and access to local parks. For instance, the area around Lake Apopka features scenic walking trails and outdoor spaces, great for leisurely strolls with pets. Additionally, the nearby Winter Garden Village provides a vibrant setting with pet-friendly shops and cafes, enhancing the overall experience for those travelling with animals.
Are there any remote work holiday rentals in Winter Garden?
In Winter Garden, Florida, there are numerous remote work holiday rentals available, with around 524 options to choose from. This charming area, known for its historic downtown and beautiful lakes, provides a conducive environment for those looking to blend work and leisure. Many of the properties come equipped with essential amenities such as free Wi-Fi, dedicated office spaces, and comfortable living areas, allowing for productive workdays.

Travellers will appreciate the proximity to local attractions, including the West Orange Trail, great for outdoor activities, and the nearby theme parks, adding a fun element to downtime. Additionally, the rentals often feature communal areas with free Wi-Fi, making it easy to stay connected while enjoying the local scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Winter Garden?
In Winter Garden, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Onsite parking is commonly available, providing convenience for those travelling by car. Many rentals also feature coffee and tea makers, superb for enjoying a warm beverage at any time of the day. Additionally, balconies are a sought-after amenity, offering outdoor space to relax and take in the surroundings. For those looking to unwind, hot tubs are often included as well, providing a luxurious way to relax after a day of exploring the area.
When is the best time to visit Winter Garden for a holiday rental?
September is a wonderful time to visit Winter Garden, Florida, particularly for those looking to escape the winter chill elsewhere. This month offers warm temperatures, typically ranging from 21 to 31 degrees Celsius, making it great for outdoor activities such as exploring the scenic West Orange Trail or enjoying the vibrant local farmers' market.

The peak season in Winter Garden runs from January to March, drawing families and sun-seekers eager to enjoy milder weather and various outdoor attractions. During this time, the area buzzes with activity, featuring events like the Winter Garden Music Festival, which showcases local talent and fosters a sense of community.

If you're seeking a more budget-friendly option, consider planning your visit in October. This month presents a quieter charm as the summer crowds have dispersed, but the weather remains pleasant for leisurely exploration of the picturesque downtown area, complete with its unique shops and dining options.
What are the top attractions in Winter Garden?
In Winter Garden, visitors can enjoy a variety of attractions that showcase the area's charm and history. The historic downtown area features a lovely selection of boutique shops, restaurants, and cafes, superb for leisurely strolls. The Winter Garden Heritage Museum offers insights into the local history and culture, housed in a beautifully restored building.

For outdoor enthusiasts, the West Orange Trail is a highlight, providing a scenic pathway for walking, cycling, and jogging that stretches through the area. Additionally, the nearby Lake Apopka offers opportunities for fishing, birdwatching, and nature walks, making it an excellent spot for those looking to immerse themselves in Florida's natural beauty. The local farmers market, held weekly in the downtown area, is also a popular attraction, showcasing fresh produce and artisanal goods.
Are all fees included in the Winter Garden holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Winter Garden holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Winter Garden 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 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.
Are there any discounts for Winter Garden holiday homes?
You can find great discounts on holiday homes in Winter Garden on Bookabach, 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.
Can I change or cancel my Winter Garden holiday home booking on Bookabach?
To find Winter Garden holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Garden?
A long-stay holiday home in Winter Garden 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Winter Garden holiday home?
Book your Winter Garden holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Garden?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winter Garden to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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