Vacation to Winter Garden

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:

Save up to 30% when you add a hotel to your flight as an Expedia member

Enjoy flexibility with our Book now Pay later option & fully refundable rates on most hotels

Customize your vacation with ease all in one place

Winter Garden Flight and Hotel Deals

The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5 out of 5
Four Corners
Save 100% on your flightPrice was $6,178, price is now $3,806 per person
per person
Apr 9 - Apr 14
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
3/5 (9 reviews)
Beautifully decorated and well maintained vacation home. Our entire family enjoyed our stay.

Reviewed on Jul 20, 2021

El Caribe Resort & Conference Center

El Caribe Resort & Conference Center

2.5 out of 5
Melinda Cook
Save 100% on your flightPrice was $1,047, price is now $670 per person
per person
Mar 10 - Mar 13
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
3.6/5 Good! (1,005 reviews)
After the Hurricane there was a lot of damage here and everywhere around, but the Staff at El Caribe went above and beyond to make sure we were taken care of.

Reviewed on Oct 17, 2022

CLC Regal Oaks Resort Vacation Townhomes

CLC Regal Oaks Resort Vacation Townhomes

4 out of 5
Save 100% on your flightPrice was $1,508, price is now $968 per person
per person
Apr 1 - Apr 8
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.1/5 Very Good! (2,319 reviews)
Second time staying here and we loved it. Staff is very friendly and the property is kept in great shape.

Reviewed on Jan 18, 2023

Westgate Palace a Two Bedroom Condo Resort

Westgate Palace a Two Bedroom Condo Resort

4 out of 5
Florida Center
Save 100% on your flightPrice was $656, price is now $429 per person
per person
Mar 24 - Mar 27
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4/5 Very Good! (1,005 reviews)
I really loved our stay at this resort, the condo was roomy enough and overall location was excellent, although some amenities were closed while we were there. The only downside was the late fee 😔 we were travelling from abroad so I hope they remove that in the future if we come back over there.

Reviewed on Jan 30, 2023

ette hotel

ette hotel

4 out of 5
Save 100% on your flightPrice was $1,054, price is now $739 per person
per person
Apr 5 - Apr 8
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
5/5 Exceptional! (10 reviews)
Truly a fantastic stay

Reviewed on Jan 17, 2023

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
  • Default Image

    Oakland

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

    Find hotel + flight trips in Oakland

Winter Garden Hotel Deals

Liki Tiki Village
Liki Tiki Village
3.5 out of 5
17777 Bali Blvd, Winter Garden, FL, 34787
The price is $98 per night from Feb 7 to Feb 8
$98
per night
Feb 7 - Feb 8
4.1/5 Very Good! (3,028 reviews)
"safe-quiet"

Reviewed on Feb 4, 2023

Liki Tiki Village
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL, 34787
Fully refundableReserve now, pay when you stay
The price is $209 per night from Feb 26 to Feb 27
$209
per night
Feb 26 - Feb 27
4.2/5 Excellent! (4,912 reviews)
"The best place to be!"

Reviewed on Feb 5, 2023

The Grove Resort & Water Park Orlando
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, 34787
Fully refundableReserve now, pay when you stay
The price is $169 per night from Mar 1 to Mar 2
$169
per night
Mar 1 - Mar 2
4.7/5 Exceptional! (1,354 reviews)
"Very nice and comfortable."

Reviewed on Feb 5, 2023

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 220 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.

Frequently asked questions

How much does a Winter Garden vacation package cost?
We make it easy to travel somewhere new, with Winter Garden packages starting from just $429. You’ll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate escape, why not add a couple of tours and experiences to your travel itinerary?
If I'm not able to travel, can I cancel my Winter Garden vacation package?
It’s good to know that you can cancel your Winter Garden booking if your travel plans have changed. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Winter Garden?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, tours and rental cars — we’ve got them all. Select a combination that best suits you and save up to $366. And of course, we do realize that a travel package is never a one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 hotels around the globe, so you can put together your very own custom-built Winter Garden vacation package.
When is the best time of year to visit Winter Garden?
If you enjoy the buzz of peak season, you’ll enjoy visiting Winter Garden in . If you’re seeking a more relaxed vibe, is a better time to visit. Don’t want to spend a fortune? You might want to avoid , when things like airfares and hotels are more expensive. is generally when you’ll pick up the best deals.
How far in advance should I book my Winter Garden vacation?
Get rewarded with the widest variety and the cheapest prices by booking your Winter Garden adventure early. Airlines generally advertise tickets around a year before departure, so start your planning as soon as you can. Having said that, Expedia is dedicated to giving you the best bargains around, so it’s always a good time to book your dream vacation!
What does an Expedia Winter Garden travel package include?
Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is decide on your favorite combination. Once you’ve made your booking, you can add on the exciting stuff like activities and sightseeing tours. Our travel packages make it easy to craft an exciting Winter Garden trip.
What should I know before booking a Winter Garden travel package?
You’ll land impressive savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning easier. So why waste money or time? Whether you’re putting together a ritzy city getaway or a low-cost family break, browse our vacation packages today.
Does Expedia offer Book Now, Pay Later Winter Garden vacation packages?
If you like to spread the cost of your hotel and flight over several payments, Expedia is here to help. Paying the full amount for your trip upfront isn’t always the best way to pay for your break, so we’ve teamed up with online lender Affirm to give you financial freedom. Book Now, Pay Later and reduce the stress of saving to travel.
Can I choose my airline with a Winter Garden Expedia vacation package?
With a vacation package, you’re always in charge. Whether you’d like to fly to Winter Garden in economy or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners worldwide.
Can I travel to Winter Garden right now?
Find info about Winter Garden quarantine policies, travel restrictions and more by heading to our Covid-19 Travel Advisor.

Popular places to visit

Image for Orange County National Golf Club

Orange County National Golf Club

4.5/5(25 reviews)

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Stroll along the lakeside or visit the amusement park in this family-friendly area.

Orange County National Golf Club
Image for Disney's Magnolia Golf Course

Disney's Magnolia Golf Course

4/5(6 reviews)

Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Magnolia Golf Course
Image for Disney's Palm Golf Course

Disney's Palm Golf Course

5/5(1 review)

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Check out the amusement park and top-notch restaurants in this family-friendly area.

Disney's Palm Golf Course

Things to do

Image for Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

$139
Per adult
84% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Image for LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$65
Per adult
84% of travellers recommend
LEGOLAND® Florida Tickets
Image for Aquatica Orlando

Aquatica Orlando

$48
Per adult
82% of travellers recommend
Aquatica Orlando
See all activities in Winter Garden

More trip options