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.
The BC Resort on the Water
Price was CA $1,340, price is now CA $924 per person
CA $924
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.8/10 Good! (18 reviews)
We had a great stay at this condo during our trip to Florida. Everything was very clean and well maintained, which made it easy to relax right away. Communication was excellent—clear, prompt, and the instructions were simple to follow from check-in to check-out. The accommodations were comfortable and nicely set up, with everything we needed for our stay. The location was a big highlight—perfect for easy beach access and close to plenty of activities. We would definitely stay here again.
Reviewed on Apr 24, 2026
The Avalon Club
Price was CA $4,465, price is now CA $2,983 per person
CA $2,983
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
Pool was tiny. The hotel was very clean and beds were comfortable.
Reviewed on May 17, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $2,820, price is now CA $2,037 per person
CA $2,037
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (950 reviews)
Great location. Super clean and entire property is well maintained. Large 2 bedroom suite with well equipped kitchen, and large laundry machines. Bar onsite was nice as well. We loved our stay!
Reviewed on May 21, 2026
Island Grand at TradeWinds
Price was CA $3,085, price is now CA $2,264 per person
CA $2,264
per person
Jun 23 - Jun 30
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
7.6/10 Good! (1,165 reviews)
The room was really nice the only problem was the air conditioning was not working in one of the rooms so it was hot
Reviewed on May 22, 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 Adaline
Hyde Park
Price was CA $1,415, price is now CA $1,290 per person
CA $1,290
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (71 reviews)
Beautiful property and in such a charming and walkable neighborhood. Will plan to stay here again.
Reviewed on Apr 29, 2026
The St. Regis Longboat Key Resort
Price was CA $3,260, price is now CA $3,145 per person
CA $3,145
per person
Jul 13 - Jul 17
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Avalon Club
Price was CA $2,681, price is now CA $1,787 per person
CA $1,787
per person
Jul 31 - Aug 3
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
Pool was tiny. The hotel was very clean and beds were comfortable.
Reviewed on May 17, 2026
The Sarasota Modern, a Tribute Portfolio Hotel
Central Sarasota
Price was CA $956, price is now CA $757 per person
CA $757
per person
Jul 9 - Jul 12
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.2/10 Very Good! (550 reviews)
We had such a great stay at The Sarasota Modern! The hotel itself is beautiful! Very modern, clean, and had such a fun vibe from the moment we walked in. The rooms were stylish and comfortable, the pool area was amazing, and the location was perfect for exploring downtown Sarasota.
The staff was also incredibly friendly and helpful throughout our stay. Valet was easy, check-in was smooth, and everything just felt relaxing and well taken care of. It definitely felt like the perfect mix of upscale and fun.
We stayed for a special occasion and it made the whole weekend feel even more memorable. Would absolutely stay here again and recommend it to anyone looking for a trendy, relaxing Sarasota getaway or staycation!
Reviewed on May 15, 2026
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Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Price was CA $1,208, price is now CA $884 per person
CA $884
per person
Jul 9 - Jul 13
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,034 reviews)
New hotel , great service. Had the marina view and was pleased.
Reviewed on May 21, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Price was CA $2,959, price is now CA $1,978 per person
CA $1,978
per person
Jul 13 - Jul 17
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
9.8/10 Exceptional! (347 reviews)
Great location,big and well maintained living space
There was a love bag infested balcony and staff was not caring about our experience
Reviewed on May 21, 2026
The Avalon Club
Price was CA $3,106, price is now CA $2,248 per person
CA $2,248
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
Pool was tiny. The hotel was very clean and beds were comfortable.
Reviewed on May 17, 2026
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