Winter Garden Vacations from $472

Winter Garden is primarily known for family-friendly attractions, offering a central urban experience. A Winter Garden vacation package can be tailored to several travel styles:

• Budget: Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center, rated 9 out of 10 by travelers, offers amenities like free breakfast and an outdoor pool, with travelers often highlighting its great value location.
• Family: The Grove Resort & Water Park Orlando, a 4-star property rated 7.8 out of 10 by travelers, is ideal for families with its family rooms, game room, and kids club, and travelers praise its delicious food.
• Luxury: For a more upscale stay, Hilton Vacation Club Aqua Sol Orlando West, a 4-star hotel rated 8.7 out of 10 by travelers, provides amenities such as a hot tub and kitchenettes, with travelers frequently mentioning the helpful staff.
• Couples: TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance, a 3.5-star hotel rated 8.8 out of 10 by travelers, features a hot tub and bar/lounge, and travelers often praise the great food.
• Pet-friendly: Homewood Suites by Hilton Orlando at Flamingo Crossings, rated 9.1 out of 10 by travelers, welcomes pets and offers kitchens and kitchenettes, with travelers appreciating the super clean rooms.

When you bundle, you can save up to 30%*. To save money on a Winter Garden package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

A Winter Garden vacation package typically costs around $1,000 per adult for a week-long trip. Lower-priced bookings are around $500 per adult, while packages with more amenities can reach up to $1,850.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

The cheapest Winter Garden vacation package deals can be as low as around $390 per adult for weekend trips. Separately, September and January typically have the lowest average monthly prices, around $750 to $760 per adult, typically for a 4-day trip. Bundling flights and hotel together also typically saves money on a week-long trip — nearly all Winter Garden packages include some savings versus booking separately, typically around $65 per adult. Longer, two-week trips can save even more, often around $95 per adult. Browse cheap vacation packages in Winter Garden on Expedia for current deals.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

The best time to go for a Winter Garden vacation package is typically during March, July, and June, which are the peak booking months for the destination. These months often align with popular travel periods for families visiting the area's attractions.


For travelers seeking more affordable options, September, January, and October tend to offer lower package prices. While these months might be quieter, they still provide a great opportunity to experience Winter Garden.

A Winter Garden vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels also offer free breakfast and outdoor pools, which can add value to your trip. Given Winter Garden's focus on family-friendly attractions, many hotels are located about 2 miles from Walt Disney World® Resort, and some properties also offer airport shuttle service.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

For families, a Winter Garden vacation package with a stay at The Grove Resort & Water Park Orlando, a 4-star property rated 7.8 out of 10 by travelers, is a strong choice. Located about 6 miles from Walt Disney World® Resort, it offers family rooms, a kids club, and a game room, with travelers often praising its delicious food and nice pool.


Couples looking for a comfortable stay might consider TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance, a 3.5-star hotel rated 8.8 out of 10 by travelers. It's about 3 miles from Walt Disney World® Resort and features a hot tub and bar/lounge, with travelers frequently highlighting the great food.


For a luxury Winter Garden vacation package, Hilton Vacation Club Aqua Sol Orlando West, a 4-star hotel rated 8.7 out of 10 by travelers, is a great option. Situated about 6 miles from Walt Disney World® Resort, it includes amenities like a hot tub and kitchenettes, and travelers frequently mention the helpful staff.


Travelers seeking the best value can find it at Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center, rated 9 out of 10 by travelers. This hotel, about 3 miles from Walt Disney World® Resort, offers free breakfast and an outdoor pool, and travelers often highlight its great value location and lovely breakfast.

Winter Garden is an excellent choice for family vacation packages, as most of the bookings for this destination are family trips. Many hotels in the area offer family-friendly amenities like family rooms, game rooms, and hot tubs, providing a comfortable stay for all ages.


For example, The Grove Resort & Water Park Orlando, a 4-star property rated 7.8 out of 10, provides family rooms and a game room, with travelers often describing the overall experience as modern. The destination is also home to major attractions like Walt Disney World® Resort, about 2 miles from central Winter Garden, and Disney's Animal Kingdom® Theme Park, about 3 miles away, offering endless entertainment for families. Your Winter Garden vacation package can be customized around these family-friendly activities.

Book your Winter Garden vacation package around 6 weeks before you travel. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 3 and 11 weeks out.


In March and from June to July are the most popular months for Winter Garden packages, so booking earlier is advisable if you're traveling during any of these months.

A Winter Garden vacation offers access to some of Florida's most popular family-friendly attractions:


Browse and book things to do in Winter Garden on Expedia.

Most Winter Garden vacation packages last around 4 days, which is a good amount of time to explore key attractions like Walt Disney World® Resort or Universal Studios Florida. This duration allows for a focused visit to the area's family-friendly entertainment options.


While nearly a third choose weekend trips, most travelers opt for week-long trips to fully experience the destination, including places like Disney Springs™.

Winter Garden is a great destination for a weekend vacation package, especially if you're looking to focus on a few key attractions. Nearly a third of travelers choose weekend trips to this area.


In a short stay, you can easily visit major theme parks like Walt Disney World® Resort, located about 2 miles from central Winter Garden, or spend a day at Magic Kingdom® Park, also about 2 miles away. A weekend trip allows for a concentrated experience of Winter Garden's family-friendly offerings.

For a Winter Garden vacation package, renting a car is highly recommended for exploring the wider area, especially given the spread-out nature of attractions. While downtown Winter Garden is small enough to walk around, many popular destinations are a short drive away.


Major roads like State Road 50, the Western Beltway (SR 429), County Road 535, and County Road 545 connect Winter Garden to surrounding areas, including Walt Disney World Resort. These routes make it easy to reach theme parks and other entertainment options. A car provides the flexibility to visit various sites at your own pace, making it a practical choice for travelers booking Winter Garden vacation packages with flights.

Winter Garden vacation package hotels are generally located to provide convenient access to the area's major attractions, often a short drive from central Winter Garden itself.


For example, Homewood Suites by Hilton Orlando at Flamingo Crossings is about 13 miles from central Winter Garden and about 3 miles from Walt Disney World® Resort. The Grove Resort & Water Park Orlando, a 4-star property, is about 15 miles from central Winter Garden and about 6 miles from Walt Disney World® Resort. Similarly, Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance is about 13 miles from central Winter Garden and about 3 miles from Walt Disney World® Resort. This means many hotels are positioned for easy access to the theme parks and entertainment hubs.

Winter Garden vacation package hotels offer convenient access to dining and shopping, particularly in areas near major entertainment complexes.


For instance, Wyndham Lake Buena Vista – Disney Springs® Area, a 4-star hotel, and Wyndham Garden Lake Buena Vista – Disney Springs® Area are both about a 5-minute walk from Disney Springs™, which is known for its array of restaurants and shops. The Holiday Inn Orlando - Disney Springs® Area by IHG is also within easy reach, about a 10-minute walk from Disney Springs™. When choosing your hotel, consider its proximity to the specific dining and retail areas you plan to visit.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winter Garden vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Winter Garden, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Winter Garden vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winter Garden getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.