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
Price was €901, price is now €574 per person
€574
per person
21 Sept - 28 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.8/10 Excellent! (3,037 reviews)
We love staying here

Reviewed on 18 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
Price was €1,125, price is now €661 per person
€661
per person
21 Sept - 28 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
The resort is pricey even for owners I spoke to.The website say 7 pools but the resort water park was not free at all even if your a guest or owner. Not cool. Also, I was double charged and had to request my $ back. It sucks because I have to wait 5-7 business days. The bathroom sink was clogged and the living room light didn’t work. I reported it and my stay was for 5 days and nobody came to check it or fix it. But overall customer service and check-in was great no complaints. My family and I enjoyed ourselves and I can recommend this Resort.

Reviewed on 19 Aug 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was €1,173, price is now €728 per person
€728
per person
21 Sept - 28 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Everything was great! Would definitely stay again.

Reviewed on 17 Aug 2025

Hilton Orlando Buena Vista Palace - Disney Springs® Area

Hilton Orlando Buena Vista Palace - Disney Springs® Area

4 out of 5
Price was €1,014, price is now €683 per person
€683
per person
21 Sept - 28 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very Good! (1,575 reviews)
The water for the shower never got hot. Also my daughter has eczema so they wouldn’t allow her in a pool unless we had a waterproof band aid . The scene was nice. Also there’s a $40 resort fee daily so if you think you paid everything on Expedia be prepared for that.

Reviewed on 20 Aug 2025

ette hotel

ette hotel

5 out of 5
Price was €1,018, price is now €687 per person
€687
per person
2 Oct - 5 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.8/10 Exceptional! (325 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on 11 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 31 Aug to 1 Sept
€106
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (4,492 reviews)
"Everything and everyone was amazing, however our room smelled like dog pee since dogs are allowed."

Reviewed on 18 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
The price is €173 per night from 21 Aug to 22 Aug
€173
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (8,368 reviews)
"Love it"

Reviewed on 18 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 2 Sept to 3 Sept
€90
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (3,688 reviews)
"no more comment"

Reviewed on 18 Aug 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 53,761 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

Aquatica Orlando

Aquatica Orlando

€42
per traveller
82% of travellers recommend
Aquatica Orlando
Indoor Karting

Andretti Indoor Karting & Games in Orlando

€27
per adult
82% 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 €574 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.