
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.

RumFish Beach at TradeWinds
Price was CA $1,661, price is now CA $1,255 per person
CA $1,255
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.2/10 Very Good! (1,960 reviews)
I wish the room was a bit bigger. The beach, restaurants, staff were all amazing.
Reviewed on May 23, 2026

Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $3,531, price is now CA $2,221 per person
CA $2,221
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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

The Avalon Club
Price was CA $2,562, price is now CA $1,728 per person
CA $1,728
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
We loved this hotel, probably my favorite of all time. Very clean, comfortable and everyone was so friendly. The front desk woman, Gabriela, was so fantastic and accommodating. We will definitely be staying at Avalon whenever we visit Clearwater!
Reviewed on May 23, 2026

Landing Apartments near Sun City Center and Riverview
Price was CA $1,996, price is now CA $1,468 per person
CA $1,468
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Bilmar Beach Resort
Price was CA $1,700, price is now CA $1,277 per person
CA $1,277
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (1,077 reviews)
The Room was exceptionally clean, Staff were warm and inviting and helpful with a smile! The view from my room was Awesome😃👍👍👍. I will be staying at The Bilmar again in the future!!!!❤️
Reviewed on May 21, 2026
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Price found within the past 48 hours. Click for updated prices.

The Ritz-Carlton, Sarasota
Central Sarasota
Price was CA $2,061, price is now CA $1,852 per person
CA $1,852
per person
Jul 29 - Aug 2
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (1,008 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 $3,559, price is now CA $3,418 per person
CA $3,418
per person
Jul 29 - Aug 2
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) 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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Price found within the past 48 hours. Click for updated prices.

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 1 day 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

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 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
We loved this hotel, probably my favorite of all time. Very clean, comfortable and everyone was so friendly. The front desk woman, Gabriela, was so fantastic and accommodating. We will definitely be staying at Avalon whenever we visit Clearwater!
Reviewed on May 23, 2026

SkyBeach Resort
Greater Pinellas Point
Price was CA $1,002, price is now CA $769 per person
CA $769
per person
Jul 10 - Jul 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (694 reviews)
Charming little motel that has nice upgrades and beautiful view. It was reasonably priced and very clean
Reviewed on May 23, 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.

Cedar Cove Resort and Cottages
Price was CA $1,685, price is now CA $1,126 per person
CA $1,126
per person
Jul 10 - Jul 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (510 reviews)
Property was great! I would definitely recommend people to stay here great place parking is a bit of an issue if you have more than one car coming in but that comes with the island pretty typical but overall great
Reviewed on May 17, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Price was CA $3,571, price is now CA $2,290 per person
CA $2,290
per person
Jul 10 - Jul 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 $2,975, price is now CA $1,986 per person
CA $1,986
per person
Jul 10 - Jul 14
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
We loved this hotel, probably my favorite of all time. Very clean, comfortable and everyone was so friendly. The front desk woman, Gabriela, was so fantastic and accommodating. We will definitely be staying at Avalon whenever we visit Clearwater!
Reviewed on May 23, 2026
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