Winter Garden Holidays

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Top Flight + Hotel Deals in Winter Garden

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

Seasons Florida Resort

2 out of 5
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.8/10 Excellent! (3,037 reviews)
Hotel was comfortable. Several restaurants within walking distance. Used the public transportation to get around the area.

Reviewed on 9 Aug 2025

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
13 Oct - 17 Oct
found 23 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,163 reviews)
Everyone was really friendly my only complaint will be the breakfast time was a lot of people and no room to sit down

Reviewed on 9 Aug 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
The room was beautiful and I loved the balcony overlooking the lake! The hotel does not have a full length mirror though. The resort has lots of amenities, but we didn’t have time for any of them and they close early, or for weather. Upon check-in, there is an overwhelming amount of information they gave us, and after a day of traveling was unsettling. We ended up for the first day of our vacation stuck with a staff member trying to sell us a time share, but with a free breakfast and $100 as a reward. The breakfast was not worth the 2 or more hours for the time share sell that we weren’t interested in the first place. They say there is no obligation to buy the time share, but they had multiple people (3 different people) speak to us and try to convince us otherwise. It really put a bad taste in our mouth for the rest of our vacation. We felt that a morning was wasted for our vacation for $100.

Reviewed on 9 Aug 2025

ette hotel

ette hotel

5 out of 5
per person
26 Sept - 3 Oct
found 1 day ago
Return direct flight included
Paris (PAR) to Orlando (MCO)
9.8/10 Exceptional! (325 reviews)
Wonderful staff and beautiful rooms

Reviewed on 8 Aug 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Great stay. The staff was very accommodating and friendly, and the room was nice, clean and comfortable.

Reviewed on 8 Aug 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 Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Top hotels in Winter Garden

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 €106 per night from 19 Aug to 20 Aug
€106
19 Aug - 20 Aug
includes taxes & fees
9.2/10 Wonderful! (4,416 reviews)
"Food. Front desk"

Reviewed on 9 Aug 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
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 €183 per night from 11 Aug to 12 Aug
€183
11 Aug - 12 Aug
includes taxes & fees
7.8/10 Good! (8,284 reviews)
"Amazing stay! The hotel was super clean, staff was friendly and helpful, and the location was perfect for exploring Orlando.The water park was amazing ,my sister had such an amazing time . I’ll definitely be back!"

Reviewed on 9 Aug 2025

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

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is €90 per night from 25 Aug to 26 Aug
€90
25 Aug - 26 Aug
includes taxes & fees
9.4/10 Exceptional! (3,607 reviews)
"Enjoyed our stayed"

Reviewed on 8 Aug 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 52,351 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.

Popular places to visit

Resurrection Catholic Church

You can find out about the history of Winter Garden with a trip to Resurrection Catholic Church. Amble around this family-friendly area's seaside and enjoy its top-notch restaurants.

Resurrection Catholic Church

Winter Garden Art Association

Rich with history, Winter Garden Art Association is a cultural attraction worth visiting in Winter Garden. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

Winter Garden Art Association

Garden Theatre

Enjoy a show at Garden Theatre, a theatre with a story to tell in Winter Garden. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Garden Theatre

What to do in Winter Garden

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Aquatica Orlando

€46
per traveller
82% of travellers recommend
Aquatica Orlando
Indoor Karting

Andretti Indoor Karting & Games in Orlando

€27
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

€13
per adult
74% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
See all activities in Winter Garden

Frequently asked questions

How much does a Winter Garden holiday package cost?
Offering great value package deals from €576 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.

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