Winter Garden Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Our guide on 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

Oakland might not have many top sights, but Bella Collina Golf Club and Winter Garden Art Association are two attractions nearby that you can check out.

Find hotels in Oakland

Winter Garden Holiday

Our pick of the best 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
The price is NZ$467 per night from 3 Aug to 4 Aug
NZ$467
3 Aug - 4 Aug
includes taxes & fees
8/10 Very good! (10,347 reviews)
"Clean room and very friendly staff."

Reviewed on 5 July 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
The price is NZ$171 per night from 2 Aug to 3 Aug
NZ$171
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (5,128 reviews)
"The breakfast buffet is very good.Unfortunately ,the staff did not tell us that the shuttle bus to Disney is a first come first serve basis so when we tried to reserve a seat there’s nothing available already.However, overall ,it was a very good experience."

Reviewed on 6 July 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
The price is NZ$192 per night from 19 July to 20 July
NZ$192
19 July - 20 July
includes taxes & fees
9.4/10 Exceptional! (5,716 reviews)
"I really enjoyed our stay for the 4th of July weekend. Staff was very friendly and helpful. We arrived early and we're able to check in. Our dog was with us and was welcomed. We will be returning in October and I look forward to staying again."

Reviewed on 5 July 2026

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 53,653 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.

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

NZ$66
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Aquatica Orlando

Aquatica Orlando

NZ$90
per traveller
86% of travellers recommend
Aquatica Orlando
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

NZ$52
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
See all activities in Winter Garden

Frequently asked questions

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

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.