Winter Garden Holidays from AU$1,061

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 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

Your Winter Garden Holiday

Come and experience this fascinating city for yourself with a Winter Garden holiday package. Consider staying in the neighbourhood of Lake Buena Vista North, which is good for shopping and dining, and your time here is sure to be unforgettable. Fill your itinerary with tours of West Orange Trail, Resurrection Catholic Church and Oakland Nature Preserve, some of the things you shouldn't miss during a trip to Winter Garden. A couple of clicks is all it takes to build a tailored Winter Garden holiday on Expedia.

The Latest Winter Garden Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Universal's Stella Nova Resort

Universal's Stella Nova Resort

3 out of 5
Price was AU$1,432, price is now AU$1,061 per person
AU$1,061
per person
4 Jan - 10 Jan
found 9 hours ago
Return flight included
Boston (BOS) to Orlando (MCO)
9.4/10 Exceptional! (1,194 reviews)

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was AU$2,012, price is now AU$1,089 per person
AU$1,089
per person
4 Jan - 10 Jan
found 9 hours ago
Return flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)
This is a unique orlando hotel that is away from all of the tourist insanity and a great peaceful oasys close to everything

Reviewed on 28 Oct 2026

DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4 out of 5
Airport North
Price was AU$1,476, price is now AU$1,063 per person
AU$1,063
per person
4 Jan - 10 Jan
found 9 hours ago
Return flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (2,703 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was AU$5,400, price is now AU$3,917 per person
AU$3,917
per person
21 Dec - 26 Dec
found 17 hours ago
Return flight included
Melbourne (MEL) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

4 out of 5
Downtown Orlando
Price was AU$1,833, price is now AU$1,338 per person
AU$1,338
per person
4 Jan - 10 Jan
found 9 hours ago
Return flight included
Boston (BOS) to Orlando (MCO)
10/10 Exceptional! (1 review)
Very nice place

Reviewed on 17 July 2026

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 Garden Theatre and West Orange Trail are two attractions nearby that you can check out.

Find hotels in Oakland

Winter Garden Holiday

Winter Garden Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
40,400
Max Temp Winter
21ºC
Max Temp Summer
32ºC
Top Sights
Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park

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
Fully refundableReserve now, pay when you stay
The price is AU$356 per night from 29 Oct to 30 Oct
AU$356
29 Oct - 30 Oct
includes taxes & fees
8.2/10 Very good! (10,948 reviews)
"Nice place"

Reviewed on 28 Oct 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 AU$121 per night from 24 Nov to 25 Nov
AU$121
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (5,688 reviews)
"All excellent love place"

Reviewed on 28 Oct 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 AU$156 per night from 11 Nov to 12 Nov
AU$156
11 Nov - 12 Nov
includes taxes & fees
Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 57,619 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

AU$48
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

AU$39
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$265
per adult
Walt Disney World® Resort Theme Park Tickets
See all activities in Winter Garden

Frequently asked questions

How much does a Winter Garden holiday package cost?
Offering great value package deals from AU$1,061 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.