Winter Garden holiday lettings

We found 34,080 holiday rentals — enter your dates for availability

Discover a selection of 33 apartments, 39 flats 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:6 Mar - 13 Mar

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

Pool
9.8 out of 10, Exceptional, (126 reviews)
Exceptional
(126 reviews)

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

Kissimmee, FL

7% off
Price is £4,535
for 7 nights, 1 home
£648 per night
includes taxes & fees
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Rock Springs Run (8.8 mi / 14.2 km)
  • Beachcomber Beach (11 mi / 17.7 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 / 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 rental?
When considering a holiday rental in Winter Garden, Florida, a popular area to stay is the historic downtown district. This charming neighbourhood is brimming with character and offers a delightful mix of shops, cafes, and restaurants along Plant Street, making it an ideal spot for those who appreciate a vibrant atmosphere. The downtown area is also home to the beautiful Winter Garden Theatre, which hosts various performances and events throughout the year, providing a cultural experience right on your doorstep.

Another appealing area is the West Orange Trail, a popular spot for outdoor enthusiasts. This well-maintained trail is superb for walking, jogging, or cycling, and it runs through picturesque landscapes, connecting to nearby parks and recreational facilities. Staying near the trail allows easy access to the natural beauty of the region while still being close to local amenities.
How much does it cost to rent a holiday home in Winter Garden?
Prices for holiday 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 holiday 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 holiday rental accomodation in Winter Garden?
In Winter Garden, condos are the most popular type of holiday rental, with around 74 available throughout the area. These condos are often situated in well-maintained communities, providing convenient access to local attractions such as the historic downtown and the West Orange Trail. Most rooms come equipped with modern amenities, including fully stocked kitchens, spacious living areas, and communal facilities like pools and fitness centres.
Are there any family house rentals in Winter Garden?
In Winter Garden, Florida, there are plenty of family-friendly house rentals available, with around 139 options to choose from. This charming area is known for its quaint downtown, where visitors can enjoy a variety of shops, restaurants, and the beautiful West Orange Trail. Many homes in this locale offer spacious living areas, fully equipped kitchens for family meals, and private outdoor spaces, superb for children to play or for hosting barbecues.
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 and hot tubs, with around 122 options to choose from. This charming area, known for its picturesque downtown and proximity to Orlando's attractions, offers a variety of neighbourhoods where these properties can be found. Many rentals are situated near the West Orange Trail, great for those who enjoy outdoor activities and cycling. Find your rental in Winter Garden with a pool or a hot tub.
Can I find long-stay holiday rentals in Winter Garden?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Garden?
In Winter Garden, there are numerous pet-friendly house rentals available, offering a variety of amenities to accommodate both travellers and their furry companions. Many of these properties feature spacious backyards, ideal for pets to roam and play, along with outdoor seating areas for guests to relax. Inside, you can expect fully equipped kitchens, comfortable living spaces, and sometimes even pet-specific amenities like dog beds or treats.
Are there any remote work holiday rentals in Winter Garden?
In Winter Garden, there are a substantial number of remote work holiday rentals available, with around 148 options to choose from. This charming town, located just outside Orlando, offers a variety of properties that cater to remote workers. Many of these rentals feature dedicated office spaces, desks with ergonomic chairs, and reliable Wi-Fi, ensuring a productive working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Garden holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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 rental amenities typically include kitchens, which allow guests to prepare their own meals, and shared pools that provide a refreshing place to relax and socialise. Many properties also feature microwaves and refrigerators, making it convenient for guests to store and heat up snacks or meals.
How early should I book a Winter Garden holiday rental?
Book your Winter Garden holiday 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 holiday 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 enjoy a variety of attractions that showcase the area's charm and history. The historic downtown area features a delightful selection of shops, restaurants, and the picturesque Winter Garden Heritage Museum, which offers insights into the region's past. The West Orange Trail is a popular spot for outdoor enthusiasts, providing a scenic route for walking, cycling, and jogging through lush landscapes.
Can I change or cancel my Winter Garden home rental booking on Vrbo?
To find Winter Garden holiday 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 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 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, Vrbo 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 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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