Winter Garden holiday lettings

We found 32,360 holiday rentals — enter your dates for availability

Select from 58 houses, 89 flats and other holiday rentals to find the perfect place for your stay in Winter Garden. 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:7 Nov - 14 Nov
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Why visit Winter Garden

  • Proximity to Theme Parks: Winter Garden is just minutes away from the magical Disney parks, offering endless entertainment for families.
  • Charming Outdoor Spaces: Enjoy the serene butterfly garden and various parks that provide lovely outdoor experiences.
  • Family-Friendly Attractions: The area offers a range of activities suitable for all ages, ensuring fun for the whole family.
  • Local Community Vibe: Experience the welcoming atmosphere of Winter Garden, perfect for relaxation and exploration.
  • Diverse Accommodation Options: Choose from an array of holiday rentals, including villas and condos, tailored to every traveller’s needs.

Popular types of accommodation in Winter Garden

You've chosen Winter Garden for your next getaway, and now it’s time to find the perfect place to stay. Whether you prefer houses, villas, or condos, our selection of holiday rentals caters to every need. Discover charming house rentals and spacious bedroom rentals that offer comfort and convenience. Dive into your Winter Garden adventure with confidence, knowing you'll have a fantastic home away from home.

  • Houses: The most sought-after option in Winter Garden, ideal for families or groups seeking a homely atmosphere during their stay.
  • Villas: A luxurious choice for those looking for spacious accommodations with upscale amenities in a picturesque setting.
  • Condos: A popular choice for couples or small families, offering convenience and comfort in a shared community.
  • Apartments: A versatile option for solo travellers or small groups, providing a cosy base for exploring the area.
  • Cottages: Charming and quaint, perfect for those seeking a rustic getaway with a touch of local character.**

Top attractions near Winter Garden

Winter Garden, Florida, is an ideal destination for family holidays, entertainment, and business trips. Visitors can enjoy a variety of attractions, including theme parks, golf courses, and arts centres. This charming locale caters to those seeking family-friendly activities, cultural experiences, and outdoor adventures, making it a perfect spot for tourists looking to explore and unwind.

  • Walt Disney World® Resort: This renowned theme park, situated 6.2km from Winter Garden, offers a magical experience filled with entertainment and family-friendly attractions. Guests can explore enchanting lands, meet beloved characters, and enjoy spectacular shows that create lasting memories.
  • Orange County Convention Center: Located 7.5km away, this vibrant arts centre showcases a rich cultural atmosphere. Visitors can attend various events and exhibitions, immersing themselves in the local arts scene and enjoying diverse performances.
  • Universal CityWalk: Just 6.2km from Winter Garden, this lively tourist precinct is perfect for families seeking outdoor fun. With an array of dining, shopping, and entertainment options, it’s a vibrant hub for relaxation and enjoyment.

Things to do recommended for couples

For a romantic getaway in Winter Garden, consider a ride on the Orlando Eye at ICON Park for stunning views, enjoy a delightful meal at Pirate's Dinner Adventure, or indulge in luxury at Windermere Country Club, perfect for couples seeking a memorable experience.

Things to do recommended for families

Families visiting Winter Garden can experience the thrills of Universal’s Volcano Bay, just 6.2km away, and enjoy the excitement of The Woods Laser Tag, 1.9km away. For sports enthusiasts, the Kia Center, located 7.5km from Winter Garden, offers a fantastic atmosphere for all ages.

Things to do recommended for groups

Groups visiting Winter Garden can enjoy a round of golf at Disney's Magnolia Golf Course, hike the scenic West Orange Trail for a taste of adventure, and catch a performance at the Garden Theatre, perfect for a night of culture and entertainment with family and friends.

What do I need to keep in mind when booking a vacation in 'Winter Garden

If you're travelling with a group, as a family, bringing along your pets, or seeking longer stays, it's important to filter your options based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winter Garden with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winter Garden 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 having 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 Winter Garden: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels 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 place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as 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, Florida, offers a delightful blend of family-friendly attractions and outdoor recreation, making it an idyllic destination for holidaymakers. Just minutes from the enchanting Disney parks, visitors can also explore the serene butterfly garden and enjoy the welcoming atmosphere of the local community. With its sunny weather and friendly vibe, Winter Garden promises a memorable experience for families and business travellers alike, perfect for unwinding and creating cherished memories.

  • Orlando: Orlando is a bustling metropolis located 8.1km from Winter Garden. Renowned for its family-friendly atmosphere and entertainment-themed experiences, visitors flock to this vibrant city to enjoy an array of attractions. From world-famous theme parks and film studios to a variety of resorts and shopping areas, Orlando offers something for everyone. Take in the cultural scene at its arts centres or unwind at nearby beaches, making it an ideal destination for both thrill-seekers and those looking to relax.
  • Ocoee: Just 1.9km away from Winter Garden, Ocoee is a charming city that promises an enjoyable experience for families and adventure enthusiasts alike. With a range of entertainment-themed activities, visitors can explore numerous shopping centres and resorts. The local attractions include theme parks and event conference venues, providing ample opportunities for fun and excitement. Ocoee's community spirit and accessible amenities make it a delightful stop during your holiday.
  • Vista del Lago: Located in close proximity to Winter Garden, Vista del Lago is a picturesque neighbourhood that offers a unique blend of family-friendly and city-themed experiences. With an array of resorts and shopping areas, as well as golf facilities, it caters to those looking for leisure and recreation. Nearby landmarks include theme parks, film studios, and a stadium, ensuring that visitors have a wealth of attractions to explore, making it a lovely addition to your travel itinerary.

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

Are you hoping to cut costs on your next getaway? It may be beneficial to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to considerable 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 provides a convenient area for you to plan new trips, manage your existing arrangements, or review your bookings. The properties you’ve saved or reserved are now neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/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:

  • Lake Butler (7.5 mi / 12.1 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 Park (13 mi / 20.9 km)
  • Lake Eola (13 mi / 21 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?
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 rental accommodation in Winter Garden?
The most desirable types of holiday rentals in Winter Garden are houses. Looking for something different? Vrbo 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 rental 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 Vrbo. 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 rentals 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 rentals on Vrbo. 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 Vrbo. Lazy soak or races and ball games? Downtime is up to you when your Vrbo holiday property comes with a swimming pool.
What are popular rental amenities in Winter Garden?
An electric car charging station, a firepit and a barbecue grill head the list of most popular rental amenities in Winter Garden. Whether you plan to travel as a party of one, with your better half or a group of dear friends, Vrbo can help you find a holiday home that suits your style with all the extras you're looking for.
Are there holiday rentals 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 rentals in Winter Garden?
Yes, Winter Garden has three one-bedroom rentals available. Usually situated in popular areas because of their compact size, a one-bedroom rental 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 rentals with air conditioning in Winter Garden?
You can pick from three holiday rentals 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 rental in Winter Garden?
The age limit can differ between properties on Vrbo, 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 rental 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 Vrbo'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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