Winter Garden Holidays

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Winter Garden Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Washington (IAD) to Orlando (MCO)
7.8/10 Good! (1,199 reviews)
I would definitely stay here again!

Reviewed on 30 Mar,2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Washington (IAD) to Orlando (MCO)
9/10 Wonderful! (1,002 reviews)
We really enjoyed having the pool attached to the house

Reviewed on 22 Mar,2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Washington (IAD) to Orlando (MCO)
8.4/10 Very Good! (1,011 reviews)
We had a great stay! However I feel it best to share both pros and cons. Pros Extremely friendly and welcoming staff. (Unfortunately I didn’t get everyone names as there were a few). I did get regular text updates from Marlyn, Wally, Devi, Richard) Check in was smooth. Everyone at the front was extremely nice and patient. Success in particular was an extremely helpful concierge. He was pleasant and helpful navigating the general area, dining recommendations and with general assistance at the property. Extremely clean rooms. Which is what was important to us. Very Spacious. Close to universal and it helps that private transportation was included to make it convenient. We made use of the cabanas which was really nice to hang out pool side. Cons There is construction so part of the street it blocked off. It didn’t affect us arriving but it did affect any deliveries trying to get to the property Dining Was very limited but we made use of delivery services No daily cleaning or turn down staff an amenity that I personal look forward to. The safe in our original room didn’t work properly and Our room lacked hot water but we were quickly changed to a new room with better pressure and lots of hot water. Small inconvenience to move however the staff took care of us right away Overall great stay for the price. Very clean. Great staff. Not overly crowded compared to resort properties. Centrally located. I would stay again.

Reviewed on 31 Mar,2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Washington (IAD) to Orlando (MCO)
9.6/10 Exceptional! (1,006 reviews)
Very clean and the staff was extremely friendly

Reviewed on 30 Mar,2025

ette hotel

ette hotel

5 out of 5
Save 100% on your flight
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Washington (IAD) to Orlando (MCO)
9.8/10 Exceptional! (278 reviews)
Excellent hotel. I highly recommend.

Reviewed on 31 Mar,2025

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
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Flamingo Crossings Town Center are some notable places to visit nearby.

Find hotels in Vista del Lago

Top hotels in Winter Garden

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
The price is S$327 per night from 27 Apr to 28 Apr
S$327
includes taxes & fees
27 Apr - 28 Apr
8/10 Very Good! (7,299 reviews)
"Overall good, but they need"

Reviewed on 30 Mar,2025

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
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 27 Apr to 28 Apr
S$185
includes taxes & fees
27 Apr - 28 Apr
9.2/10 Wonderful! (3,957 reviews)
"The rooms were great and the staff were very friendly and helpful. Didn't know you have to pay to park your car on the property. Also, I booked this property because it advetised shuttle service to Disney, but found out you have to make reservations 24 hours in advance. The shuttle was already full, ..."

Reviewed on 31 Mar,2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is S$175 per night from 20 Apr to 21 Apr
S$175
includes taxes & fees
20 Apr - 21 Apr
9.4/10 Exceptional! (2,775 reviews)
"Our go to property when in Orlando area."

Reviewed on 31 Mar,2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 52,759 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 holiday package cost?
Offering great value package deals from S$508 on Expedia, you’ll be thrilled with how little a holiday 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’re hoping to snag a cheap Winter Garden holiday package, consider visiting in February, September and October. You’ll typically find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winter Garden?
When planning your Winter Garden holiday, a handful of days will be enough to tour the top spots. Make sure to stop by Carter Family Bowl — it’s one of the most popular attractions in this destination. If you’re looking for more activities, consider basing yourself here and heading off on some day tours from Winter Garden.
Is it worth booking a holiday package to Winter Garden?
Well known for its cycling, markets and shopping, a Winter Garden holiday is a hit with all types of travellers. Be sure to check out leading sights like Resurrection Catholic Church and West Orange Trail, and consider renting a car for day trips to explore even more.
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 customise your search by “Property class,” “Number of bedrooms,” “Traveller 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation 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 holiday package to Winter Garden?
If you’ve got your Winter Garden holiday 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. Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday in Winter Garden.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the largest expense during your trip to Winter Garden.
  3. Decide your trip length: Think about how much time you want to spend exploring Winter Garden. Plan your days so you can get to all the attractions and experiences you’re interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to pick a Winter Garden holiday package that brings all your bookings together.

Popular places to visit

Disney's Magnolia Golf Course

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

Central Florida Railroad Museum

You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your trip to Winter Garden. Amble around this family-friendly area's lakeside or seek out the adventure tours.

Central Florida Railroad Museum

What to do in Winter Garden

Eco-Kayak Tour

Guided Eco-Paddle

S$79
per traveller
Guided Eco-Paddle
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$101
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
WonderWorks All Access After Dark

WonderWorks All Access After Dark

S$37
per traveller
86% of travellers recommend
WonderWorks All Access After Dark
See all activities in Winter Garden

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.