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Legacy Trail Luxury Holidays

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Top Luxury holiday packages in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
  • 40-inch TV with cable channels
    25 Aug - 29 Aug

    Royal North Beach All Suites + Flight

    Clearwater Beach
    4 nights
    3.0 star property
    7.8/10 - Good (1,000 reviews)
    "Clean"
    Reviewed July 20, 2026
    Return • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Direct TPA - YYZ • 1 stop
    €671
    €555
    per traveller
    found 1 day ago
    Royal North Beach All Suites
  • Living area
    25 Aug - 29 Aug

    CW Hotel + Flight

    Clearwater Beach
    4 nights
    4.0 star property
    9.6/10 - Exceptional (24 reviews)
    "We stay for 3 nights, They did not clean up our room until we cek out, they just come 1 hour before we cek out, but that too late because we will leave the rooms. we only cleaned up by ourselves during our vacation. The location is perfect very close with the beach and shopping area. I would like to stay in this hotel again next time, i wish the cleaning service can cleanup my room every days."
    Reviewed July 24, 2026
    Return • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Direct TPA - YYZ • 1 stop
    €1,026
    €739
    per traveller
    found 1 day ago
    CW Hotel
  • Outdoor pool, pool umbrellas, pool loungers
    25 Aug - 29 Aug

    Wyndham Grand Clearwater Beach + Flight

    Clearwater Beach
    4 nights
    4.0 star property
    9.4/10 - Exceptional (3,580 reviews)
    Return • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Direct TPA - YYZ • 1 stop
    €1,178
    €870
    per traveller
    found 1 day ago
    Wyndham Grand Clearwater Beach
  • Grand Suite, 3 Bedrooms, Ocean View | Terrace/patio
    25 Aug - 29 Aug

    The Avalon Club + Flight

    Clearwater Beach
    4 nights
    4.0 star property
    9.4/10 - Exceptional (573 reviews)
    "I loved the location. Check in was a little slow because there was only one person manning the desk and the phone was ringing. I was under the impression that I booked a 3 bedroom villa with an ocean view. When I got to my room, I was disappointed because there was no view. Apparently, if you book through Expedia you have to explicitly state your preference (ocean, marina, or city view). This was not my understanding and so I was disappointed because the room as expensive and the main reason I..."
    Reviewed July 23, 2026
    Return • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Direct TPA - YYZ • 1 stop
    €1,124
    €869
    per traveller
    found 1 day ago
    The Avalon Club
  • View from property
    25 Aug - 29 Aug

    Pelican Pointe Clearwater Beach Hotel + Flight

    Clearwater Beach
    4 nights
    2.5 star property
    8.8/10 - Excellent (1,066 reviews)
    "The room was excellent! Very clean and spacious. We had a queen with a separate seating area that had a full size futon that folded out. We walked to the beach both mornings and were within walking distance of many breakfast, lunch and dinner options. We thoroughly enjoyed our stay and were very pleased with location and our room. The pool was not very clean but it could have been due to all the small trees bordering the pool."
    Reviewed July 24, 2026
    Return • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Direct TPA - YYZ • 1 stop
    €750
    €606
    per traveller
    found 1 day ago
    Pelican Pointe Clearwater Beach Hotel

All you need to know about luxury holidays in Legacy Trail

What can I expect from a luxury Legacy Trail holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Legacy Trail?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Legacy Trail holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Legacy Trail?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Legacy Trail starting at €555. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Legacy Trail?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Legacy Trail spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Legacy Trail?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Legacy Trail?

You can wangle a top-notch luxury holiday in Legacy Trail for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Legacy Trail with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Legacy Trail with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Legacy Trail to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.