Winter Garden holiday homes

We found 33,353 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Winter Garden to find one that's 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:6 Nov - 13 Nov

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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)
  • Universal’s Volcano Bay (9.9 mi / 16 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)

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:

  • Clarcona Horseman's Park (6.6 mi / 10.6 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)
  • Tinker Field (11.2 mi / 18 km)
  • Lake Eola (13 mi / 20.9 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 home?
Vista del Lago is one of the most desired neighbourhoods to book a holiday property in Winter Garden. Stay here to enjoy the relaxation and comfort that comes with having a place to yourself.
What is the most popular type of holiday home accommodation in Winter Garden?
The most desirable types of holiday homes in Winter Garden are houses. Looking for something different? Bookabach has numerous options to match our guests' needs, so you'll see holiday properties in all sizes and shapes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Winter Garden?
The average price for a holiday home in Winter Garden is based on several factors, like time of year, length of stay and property type. Whether you're in search of a sprawling villa with space for extended family or a comfy cabin just for the two of you, just add your dates of travel to discover stays with terrific value.
How much does it cost to rent a beach house in Winter Garden?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Winter Garden travel dates to see your options on Bookabach. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Winter Garden?
Pack a tug toy and treats for your puppy dog because Winter Garden has four stays that throw out the welcome mat to pets. Let your furriest friend get in on the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your destination and dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Garden?
Tick the "pool" box in our filter tool and you'll find two houses with private pools in Winter Garden on Bookabach. Lazy soak or races and ball games? Downtime is up to you when your Bookabach holiday property comes with a swimming pool.
What are popular home amenities in Winter Garden?
An electric car charging station, a firepit and a barbecue grill head the list of most popular home amenities in Winter Garden. Whether you plan to travel as a party of one, with your better half or a group of dear friends, Bookabach can help you find a holiday home that suits your style with all the extras you're looking for.
Are there holiday homes in Winter Garden that welcome kids?
With four family-friendly holiday properties to select from in Winter Garden, now is a fantastic time to introduce your children to the joys of travel. Just click on our "Properties good for families" filter to find stays packed with conveniences perfect for travelling families, such as multiple bedrooms, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in Winter Garden?
Keeping the kids happy during your stay in Winter Garden is a cinch with these cool family-friendly attractions:

  • Universal Studios Florida
  • The Wizarding World of Harry Potter™
  • Winter Garden Heritage Museum

Are there one-bedroom holiday homes in Winter Garden?
Yes, Winter Garden has three one-bedroom homes available. Usually situated in popular areas because of their compact size, a one-bedroom home is ideal if you're getting away with your partner or a pal. And with comforts such as kitchens and more privacy than a standard hotel, you'll be able to kick back while sightseeing around this amazing destination.
How can I find holiday homes with air conditioning in Winter Garden?
You can pick from three holiday homes with air conditioning in Winter Garden providing that cooling breeze and extra bit of comfort. Simply enter your desired travel dates and then make use of our filter tool to look for stays with air conditioning.
How old do you have to be to rent a holiday home in Winter Garden?
The age limit can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Winter Garden you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Winter Garden for?
It all depends on the Winter Garden property. To view a list of options offering extended stays, just enter your travel dates and number of guests into Bookabach's search page. Enjoy having the whole place to yourself, along with amenities such as a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

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