A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Winter Garden Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Winter Garden vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Sept 24 - Sept 30

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    6 nights
    3.0 star property
    8.4/10 - Very good (5,222 reviews)
    "Helpful staff"
    Reviewed July 19, 2026
    Roundtrip Toronto (YTO) - Orlando (MCO)
    YYZ - MCO1 stop MCO - YYZ1 stop
    CA $1,781
    CA $605
    per traveller
    found 1 day ago
    Palazzo Lakeside Hotel
  • Sept 24 - Sept 30

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    6 nights
    4.0 star property
    8.4/10 - Very good (6,721 reviews)
    Roundtrip Toronto (YTO) - Orlando (MCO)
    YYZ - MCO1 stop MCO - YYZ1 stop
    CA $1,275
    CA $742
    per traveller
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area
  • Aug 23 - Aug 29

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,005 reviews)
    Roundtrip Toronto (YTO) - Orlando (MCO)
    YYZ - MCO1 stop MCO - YYZ1 stop
    CA $2,653
    CA $1,554
    per traveller
    found 2 days ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Sept 24 - Sept 30

    Seasons Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (3,719 reviews)
    "Nice/clean place"
    Reviewed July 18, 2026
    Roundtrip Toronto (YTO) - Orlando (MCO)
    YYZ - MCO1 stop MCO - YYZ1 stop
    CA $969
    CA $611
    per traveller
    found 1 day ago
    Seasons Florida Resort
  • Sept 4 - Sept 7

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,291 reviews)
    Roundtrip Montreal (YMQ) - Orlando (MCO)
    YUL - MCO1 stop MCO - YULNonstop
    CA $1,315
    CA $831
    per traveller
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive

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
Learn more about Winter Garden

Downtown Winter Garden

Historic Downtown Winter Garden charms visitors with its beautifully preserved early 20th century buildings along brick-lined Plant Street. The restored 1935 Garden Theatre anchors this pedestrian-friendly district where wide sidewalks invite leisurely exploration. Regular street events and a popular farmers market create a lively atmosphere throughout the week. Cyclists will love accessing the scenic West Orange Trail that runs through downtown. History buffs can explore the Central Florida Railroad Museum and Heritage Museum to discover local stories. The area's artisanal shops, farm-to-table restaurants, and outdoor dining spots make this walkable district perfect for a relaxed Florida getaway.

Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

Vista del Lago

Vista del Lago offers a peaceful retreat just minutes from Orlando's world-famous attractions. This welcoming Four Corners community features resort-style amenities including sparkling pools and recreation areas. Families appreciate the quiet residential setting after busy theme park days. Wide streets lined with Mediterranean-style vacation homes create a relaxing atmosphere for travellers. Disney's Animal Kingdom and Magic Kingdom are just a short drive away. Most visitors enjoy having kitchen facilities and private spaces while staying close to Orlando's excitement.

Oakland

Oakland charms visitors with its well-preserved historic buildings and small-town atmosphere just outside Orlando's bustling tourist zones. Victorian homes line oak-canopied streets while the downtown area offers antique shops and local cafes. The 128-acre Oakland Nature Preserve provides scenic boardwalks through cypress wetlands. Lake Apopka shoreline offers excellent bird watching with over 200 species. History buffs will appreciate the 1889 Healthy House Museum and railroad heritage. Most businesses close early, creating a peaceful evening environment. The West Orange Trail connects cyclists to Winter Garden's wider area.

Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. This family-friendly suburb surrounds you with manicured lawns, palm trees, and quiet residential streets. The nearby West Orange Trail and Lake Apopka provide perfect settings for outdoor recreation. Budget-conscious travellers will appreciate the affordable accommodations and relaxed atmosphere. Take morning strolls along spacious sidewalks or visit Oakland Nature Preserve just minutes away. A car is essential for exploring Winter Garden's charming downtown and reaching Orlando's famous attractions.

Discover the most popular places to visit in Winter Garden

What to do in Winter Garden

Winter Garden Hotel Deals

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 vacation package cost?

You can grab a vacation package to this destination from CA $605 on Expedia. But how much your vacation to Winter Garden costs will depend on factors like the season, length of stay and hotel choice.

What are the cheapest months to go to Winter Garden?

You're likely to find lower prices and greater availability in February, September and October. Browse our cheap Winter Garden vacation packages and you could get some great off-season deals.

How many days is enough for Winter Garden?

You can visit all the major attractions in Winter Garden in a few days, including the popular Winter Garden Art Association. If you're after a longer Winter Garden vacation, check out what kind of activities and excursions are available in the area.

Is it worth booking a vacation package to Winter Garden?

Winter Garden has everything you need for a fantastic break — cycling, markets and shopping are just the start. Whether you want to visit sights such as Resurrection Catholic Church and West Orange Trail, or venture off the beaten track, you'll have plenty to experience on your Winter Garden vacation.

How to find the best Winter Garden package deals?

Finding a cheap Winter Garden package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" 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 often lower.

Is it cheaper to book a Winter Garden vacation as a package?

You can enjoy significant savings on your Winter Garden break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Winter Garden?

Score incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winter Garden escape.

How to plan a trip to Winter Garden?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Winter Garden.
  2. Set your budget: Consider costs like flights, meals and transportation when working out how much to save for your trip to Winter Garden. Then, select a hotel that suits your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Winter Garden. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winter Garden vacation 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.