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A tree-lined sidewalk with parked cars and a clear sky.

Downtown Winter Garden Vacations from ￥294,511

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The Latest Downtown Winter Garden Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Aerial view
    Oct 10 - Oct 16

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Enjoyed my stay will rebook again"
    Reviewed July 31, 2026
    Roundtrip • Tokyo (TYO) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 2 stops
    ￥461,446
    ￥294,511
    per traveler
    found 16 hours ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • 4 outdoor pools, cabanas (surcharge), sun loungers
    Sep 22 - Sep 28

    Club Wyndham Bonnet Creek + Flight

    Orlando
    6 nights
    3.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip • Tokyo (TYO) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥627,545
    ￥473,909
    per traveler
    found 20 hours ago
    Club Wyndham Bonnet Creek
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sep 22 - Sep 28

    Hyatt Regency Orlando + Flight

    International Drive District
    6 nights
    4.5 star property
    9.2/10 - Wonderful (2,084 reviews)
    Roundtrip • Tokyo (TYO) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥824,372
    ￥626,915
    per traveler
    found 20 hours ago
    Hyatt Regency Orlando
  • 4 outdoor pools, cabanas (surcharge), pool umbrellas
    Sep 22 - Sep 27

    Hilton Vacation Club Mystic Dunes Orlando + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.0/10 - Wonderful (4,816 reviews)
    Roundtrip • Tokyo (TYO) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥552,872
    ￥427,826
    per traveler
    found 20 hours ago
    Hilton Vacation Club Mystic Dunes Orlando
  • Aerial view
    Sep 22 - Sep 27

    Villatel Resort Orlando + Flight

    Orlando
    5 nights
    4.0 star property
    9.4/10 - Exceptional (515 reviews)
    "Very nice place for families during the summer. Kids had a lot of fun in the waterpark!"
    Reviewed July 31, 2026
    Roundtrip • Tokyo (TYO) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥735,226
    ￥570,663
    per traveler
    found 20 hours ago
    Villatel Resort Orlando

Discover the most popular places to visit in Downtown Winter Garden

West Orange Trail

8.4/10 (337 reviews)
Enjoy a trip to West Orange Trail and popular activities like taking adventure tours in Winter Garden. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

What to do near Downtown Winter Garden

Picture 1 for Activity Whispers on the Wharf: Winter Garden Ghost Tours

Whispers on the Wharf: Winter Garden Ghost Tours

￥3,901
per adult
0% of travelers recommend
Whispers on the Wharf: Winter Garden Ghost Tours
See all activities near Downtown Winter Garden
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.