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.
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Price was CA $1,212, price is now CA $915 per person
CA $915
per person
Jul 23 - Jul 26
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,008 reviews)
We really enjoyed our stay, close to the beach and all the amenities you could ask for!
Reviewed on May 13, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $2,812, price is now CA $1,775 per person
CA $1,775
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (950 reviews)
Our room was very clean, looked like the pictures, beds were comfy and the staff was very helpful.
Reviewed on May 18, 2026
Landing Apartments near Sun City Center and Riverview
Price was CA $2,155, price is now CA $1,627 per person
CA $1,627
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (29 reviews)
Is great property but be very careful on location of unit. The external doors are very loud when they open and close and if you are close it will disturb you thru night. Everything else was so great though. That was really our only complaint. I highly recommend it, just pay attention to location of unit.
Reviewed on Apr 29, 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 Ritz-Carlton, Sarasota
Central Sarasota
Price was CA $1,946, price is now CA $1,756 per person
CA $1,756
per person
Aug 2 - Aug 6
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Location of the property is wonderful. The shuttle bus to the private beach and Armond Circle was wonderful. We used it everyday. The drivers were super nice. The property is well maintained and the staff is so helpful and friendly.
Reviewed on May 18, 2026
The St. Regis Longboat Key Resort
Price was CA $2,898, price is now CA $2,788 per person
CA $2,788
per person
Aug 2 - Aug 6
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (72 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.
Hotel Alba, Tapestry Collection by Hilton
Westshore
Price was CA $962, price is now CA $747 per person
CA $747
per person
Jul 23 - Jul 26
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (2,590 reviews)
Hotel wasn’t bad, the room door wasn’t sealed properly so there were bugs in the room. They were doing construction on the road beside the hotel. We asked for a room further away in the main building and they didn’t help us put. Literally did nothing about it. The whole room was shaking during the night. I know it’s not the hotel fault, but they should’ve accommodated us with a room in the main building where it would have been quieter.
Reviewed on May 18, 2026
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Price was CA $1,212, price is now CA $915 per person
CA $915
per person
Jul 23 - Jul 26
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,008 reviews)
We really enjoyed our stay, close to the beach and all the amenities you could ask for!
Reviewed on May 13, 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.
Holiday Inn Express Lake Wales N-Winter Haven by IHG
Price was CA $1,188, price is now CA $900 per person
CA $900
per person
Jul 16 - Jul 20
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,020 reviews)
Front desk staff was very friendly!
Reviewed on May 18, 2026
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