Legacy Trail Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Legacy Trail
Price found within the past 48 hours. Click for updated prices.
Landing Tampa Westshore
Port Tampa City
Price was CA $1,911, price is now CA $1,354 per person
CA $1,354
per person
Aug 8 - Aug 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (191 reviews)
Very nice and clean. We didn’t want to leave. Felt very at home. Fully furnished but if you’re a cook, bring seasonings.
Reviewed on May 5, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $3,212, price is now CA $2,013 per person
CA $2,013
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (950 reviews)
The room(s) was outstanding. Everything you needed, just like being at home. The pool was small and to many kids playing ball, that made it not useable. The beach access was more of a walk than what we wanted, no chairs on the beach that were provided by the club & no restaurants on site.
Reviewed on May 25, 2026
Wyndham Grand Clearwater Beach
Price was CA $3,587, price is now CA $2,416 per person
CA $2,416
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,252 reviews)
My experience at this hotel was fantastic! Well worth the price! View from balcony wonderful. Everyone I encountered (all staff) extremely polite and accommodating. Food was great (even though a bit pricey). Very clean everywhere, even the public restrooms. Well maintained hotel. Heated pool and concierge service pool side phenomenal. Definitely spoiled me as to what to expect on my next vacation.
Reviewed on May 25, 2026
Island Grand at TradeWinds
Price was CA $2,340, price is now CA $1,676 per person
CA $1,676
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.6/10 Good! (1,165 reviews)
Beach was beautiful and staff there were very kind and helpful and its very family friendly
Reviewed on May 24, 2026
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View all trips5* Pet-friendly holidays in Legacy Trail
Price found within the past 48 hours. Click for updated prices.
The St. Regis Longboat Key Resort
Price was CA $4,049, price is now CA $3,487 per person
CA $3,487
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
9.8/10 Exceptional! (73 reviews)
The St. Regis Longboat Key is on a level of its own. Nothing comes close to the staff and the level of detail with every thing…and I mean everything! Unparalleled excellence! Stunning property!
Reviewed on May 11, 2026
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View all trips3 Night Pet-friendly holidays in Legacy Trail
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach
Price was CA $1,435, price is now CA $1,087 per person
CA $1,087
per person
Jul 17 - Jul 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,252 reviews)
My experience at this hotel was fantastic! Well worth the price! View from balcony wonderful. Everyone I encountered (all staff) extremely polite and accommodating. Food was great (even though a bit pricey). Very clean everywhere, even the public restrooms. Well maintained hotel. Heated pool and concierge service pool side phenomenal. Definitely spoiled me as to what to expect on my next vacation.
Reviewed on May 25, 2026
Island Grand at TradeWinds
Price was CA $1,558, price is now CA $1,209 per person
CA $1,209
per person
Jul 3 - Jul 6
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.6/10 Good! (1,165 reviews)
Beach was beautiful and staff there were very kind and helpful and its very family friendly
Reviewed on May 24, 2026
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View all trips4 Night Pet-friendly holidays in Legacy Trail
Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites
Price was CA $983, price is now CA $666 per person
CA $666
per person
Jul 10 - Jul 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (79 reviews)
Great for older people who want an easily accessible room in a quiet setting. We will be back!
Reviewed on May 7, 2026
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
