A wooden pathway surrounded by dense greenery and trees.

Legacy Trail All inclusive Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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 All inclusive vacation packages in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
  • Oct 5 - Oct 8

    Saddlebrook Resort + Flight

    Wesley Chapel South
    3 nights
    4.0 star property
    8.0/10 - Very Good (139 reviews)
    "The property for the most part looked good, there were renovations being conducted. The staff was amazing, from front desk, to valet, and restaurant staff. However, the cleanliness of the property was disappointing. There were ants in the room, cobwebs were noticeable, and the tubs and showers had not been properly cleaned(which we ended up doing ourselves because we typically do that anyway while traveling). I did express that during my checkout just so they were aware of the issue. Overall a..."
    Reviewed July 12, 2026
    Roundtrip Tokyo (TYO) - Tampa (TPA)
    HND - TPA1 stop TPA - NRT1 stop
    ¥252,171
    ¥231,707
    per traveler
    found 1 day ago
    Saddlebrook Resort
  • Oct 5 - Oct 8

    The Barrymore Hotel Tampa Riverwalk + Flight

    Downtown Tampa
    3 nights
    3.0 star property
    8.6/10 - Excellent (2,703 reviews)
    "No hot water! Mentioned it to staff twice and still no hot water! Girl at checkin was very nice and so were the staff, clearly not the front desk issue but no help was frustrating. Did get offered a room change as we were leaving for the day and had a meeting, i agreed and said when we come back if its still not fixed we can move and when i got back the shift change had no idea what i was told and did not move us."
    Reviewed July 16, 2026
    Roundtrip Tokyo (TYO) - Tampa (TPA)
    HND - TPA1 stop TPA - NRT1 stop
    ¥274,632
    ¥251,985
    per traveler
    found 1 day ago
    The Barrymore Hotel Tampa Riverwalk
  • Oct 5 - Oct 8

    DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto + Flight

    North Redington Beach
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    "This is our second time to stay here - demo / construction has been going on with the properties on each side but it’s understandable considering the hurricane(s) a few years ago. We would still highly recommend and the demo to the south should be finishing up asap. Get with Kevin on the beach for your chairs / umbrellas - he’s wonderful!"
    Reviewed July 12, 2026
    Roundtrip Tokyo (TYO) - Tampa (TPA)
    HND - TPA1 stop TPA - NRT1 stop
    ¥264,987
    ¥243,915
    per traveler
    found 1 day ago
    DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
  • Oct 5 - Oct 8

    Hilton St. Petersburg Carillon Park + Flight

    St. Petersburg
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,001 reviews)
    "We booked this to start our Anniversary trip, but were sadly disappointed. At the front desk, I was asked if I wanted the balcony to overlook the parking lot and I was very shocked that she was asking since it was our anniversary and I booked a balcony room. We were told we were “upgraded” but our room was tiny-balcony was beautiful though. The first night, we had a screaming baby next door. We let the front desk know. The following night, we had someone yanked at the door in between our room..."
    Reviewed July 14, 2026
    Roundtrip Tokyo (TYO) - Tampa (TPA)
    HND - TPA1 stop TPA - NRT1 stop
    ¥268,321
    ¥249,923
    per traveler
    found 1 day ago
    Hilton St. Petersburg Carillon Park
  • Oct 5 - Oct 8

    The Westshore Grand, A Tribute Portfolio Hotel, Tampa + Flight

    Beach Park
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,849 reviews)
    "Good 👍"
    Reviewed July 16, 2026
    Roundtrip Tokyo (TYO) - Tampa (TPA)
    HND - TPA1 stop TPA - NRT1 stop
    ¥246,538
    ¥231,893
    per traveler
    found 1 day ago
    The Westshore Grand, A Tribute Portfolio Hotel, Tampa

All-inclusive Legacy Trail vacations: everything you need to know

Can I book a Legacy Trail vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Legacy Trail all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Legacy Trail?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just ¥231,707. Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Legacy Trail?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Legacy Trail vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Legacy Trail family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Legacy Trail?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Legacy Trail package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

Why should I book an all-inclusive Legacy Trail package vacation with Expedia?

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.