
Legacy Trail Vacation Packages
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Top Legacy Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Avalon Club
Save 100% on your flight
per person
Aug 16 - Aug 19
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.
Reviewed on Jul. 10, 2025


Cedar Cove Resort and Cottages
Save 100% on your flight
per person
Aug 24 - Aug 31
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
9.2/10 Wonderful! (445 reviews)
My family and I had a wondeful stay here, beds were comfortable, ac worked well, friendly and attentive staff, etc. Definitely recommend staying here and will be back soon.
Reviewed on Jun. 20, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (269 reviews)
Everything was wonderful from start to finish!! We love the location on Siesta key beach! We stayed in a spacious 3 bedroom, 3 bath villa with a nice terrace. The villas are absolutely beautiful with everything you can imagine. Top of the line everything in the kitchen and baths. Nespresso machine, blender... added to the enjoyment. Shampoo, cond & body wash in each shower, and small tubes of lotions available; basic kitchen supplies and laundry detergent. The property is small with only about 44 units, which we enjoyed and it didn't seem crowded. Easy beach access with plenty of chairs and umbrellas for your use at no charge. A lot of pool side loungers and cabanas also free of charge and first come basis. Also available a small fitness club, 2nd floor terrace with pool and ping pong tables, an owners lounge and breakfast spot. Breakfast every day is included and had pastries, oatmeal, cereal, yogurt, fruits, and hard boiled eggs, coffee, tea, milk & juice. These are high end timeshare ownership type villas and it was definitely a step above your typical villa. Service was wonderful and helpful. We were able to use the property after check out as we had a late flight and there are showers in the fitness center with towels etc. There is a small bar poolside; drinks are expensive, but potent!! :) They do offer a small menu, but we did not order any food. Short walk to restaurants, convenience store, sandwich shop, ice cream.Highly recommend!
Reviewed on Jul. 5, 2025

Wyndham Grand Clearwater Beach
Save 100% on your flight
per person
Sep 6 - Sep 13
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Great hotel in a prime position with most things in walking distance. Room was large and clean. Guests were a mixture of families and couples. Daily service charge high, but same for most similar hotels and unfortunately valet only which is also a high daily rate. That said, we walked most places and didn’t use the car most days.
Reviewed on Jul. 17, 2025
Legacy Trail Hotel Deals

Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Aug 3 to Aug 4
CA $90
CA $118 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (4,135 reviews)
"The only thing that we could have used is an umbrella or two in the pool area, everything else was superb especially the two gentlemen at the front desk."
Reviewed on Jul. 17, 2025

Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 3 to Aug 4
CA $197
CA $253 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (4,766 reviews)
"Great location. Close to private beach and walking distance to awesome restaurants and nightlife. Very friendly staff."
Reviewed on Jul. 13, 2025

Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Aug 17 to Aug 18
CA $232
CA $295 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,571 reviews)
"Beautiful resort, amazing view friendly staff"
Reviewed on Jul. 15, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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