Winter Garden Vacations from $273

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Your Winter Garden Vacation

Come and discover this interesting city for yourself with a Winter Garden vacation package. Consider basing yourself in the neighborhood of Lake Buena Vista North, which is great for shopping and dining, and your time here will be nothing short of unforgettable. Like to start exploring your surroundings? West Orange Trail, Winter Garden Art Association and Winter Garden Heritage Museum are among the leading places to visit during a trip to Winter Garden. Whoever you're heading away with and whatever your budget, your ultimate Winter Garden vacation is just clicks away with Expedia.

The Latest Winter Garden vacation packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $551, price is now $273 per person
$273
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9/10 Wonderful! (3,664 reviews)
Air conditioning was great along with the shower. Would stay again!

Reviewed on Jul 11, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,313, price is now $467 per person
$467
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Family oriented

Reviewed on Jul 10, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $767, price is now $311 per person
$311
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (1,979 reviews)
Everything was great thanks

Reviewed on Jul 12, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was $761, price is now $311 per person
$311
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
This was our 2nd time staying here. Rooms are amazing. Highly recommended.

Reviewed on Jul 5, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $840, price is now $383 per person
$383
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (6,621 reviews)
.

Reviewed on Jul 12, 2026

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Where to stay in Winter Garden

Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden
A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland

When in Oakland, you can plan a visit to Bella Collina Golf Club and Winter Garden Art Association, some noteworthy sights in the nearby area.

Find hotels in Oakland

Stay near popular Winter Garden attractions

Flamingo Crossings Town Center

8.6/10 (131 reviews)
This convenient retail hub at Disney World's western gateway offers diverse shopping and dining options. Explore Target, Walgreens, and restaurants in a pedestrian-friendly environment perfect for a theme park break.
See properties

What to do in Winter Garden

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$39
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$213
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$34
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
See all activities in Winter Garden

Winter Garden Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $252 total per night from Aug 11 to Aug 12
$252 total
Aug 11 - Aug 12
Total with taxes and fees
8/10 Very Good! (10,424 reviews)
"Amazing water park great having Starbucks on property big spacious rooms"

Reviewed on Jul 12, 2026

The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

3 out of 5
631 FLAGLER AVE Winter Garden FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Jul 29 to Jul 30
$104 total
Jul 29 - Jul 30
Total with taxes and fees
9.4/10 Exceptional! (5,186 reviews)
"Great place to stay for a Disney World family trip. All parks are less than a 15 min drive. The hotel is located across the street from a shopping center with a small Target, so perfect to get things you need. Will be staying here again."

Reviewed on Jul 12, 2026

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Jul 22 to Jul 23
$110 total
Jul 22 - Jul 23
Total with taxes and fees
9.4/10 Exceptional! (5,769 reviews)
"Great place to stay for families heading to Disney theme parks. Clean rooms and safe lighted parking place. Shoutout to front desk staff Paula for helping us find the perfect floor with quiet sleeping and great service. It made the whole Orlando Theme Park experience 2 x as nice. We highly recommend ..."

Reviewed on Jul 11, 2026

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 53,326 properties in Winter Garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winter Garden Vacation Packages

Winter Garden Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
40,400
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park

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Frequently asked questions

How much does a Winter Garden vacation package cost?
Offering great value package deals from $273 on Expedia, you'll be thrilled with how little a vacation to Winter Garden costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winter Garden?
If you'd like to snag a cheap Winter Garden vacation package, consider visiting in April, May and December. You'll typically find lower prices on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Winter Garden?
For a Winter Garden vacation, a handful of days will be enough to explore the highlights. Make sure to stop by Carter Family Bowl — it's one of the most popular sights in this destination. If you're looking for more activities, consider basing yourself here and going on some tours from Winter Garden.
Is it worth booking a vacation package to Winter Garden?
Winter Garden has everything you need for a memorable trip — cycling, markets and shopping are just the start. Whether you'd like to check out sights like Resurrection Catholic Church and West Orange Trail, or take the path less traveled, you'll have plenty to do on your Winter Garden vacation.
How to find the best Winter Garden package deals?
Landing a cheap Winter Garden package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Winter Garden package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winter Garden vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Winter Garden escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winter Garden?
If you've got your Winter Garden vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Winter Garden?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Winter Garden.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Winter Garden.
  3. Explore Winter Garden with Expedia's trip planning tool: Gain insights into the leading attractions and best stays for your trip to Winter Garden. You can also save your favorite locations, collaborate with family and friends and manage your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Winter Garden, you can work out the right length of your vacation. Put together a rough plan and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Winter Garden vacation package.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Winter Garden. Find all the exciting things to do in Winter Garden in Winter Garden with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Winter Garden vacation packages?
Set off on your ideal getaway to Winter Garden with Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up travel deals while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.