Legacy Trail Vacation Packages
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Top Legacy Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $2,302, price is now CA $1,402 per person
CA $1,402
per person
May 12 - May 18
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
The room was positively spotless and beds and bathrooms so clean. Very well stocked with dishes and cookware too!
Reviewed on Feb 23, 2026
Plaza Beach Hotel Beachfront Resort
Price was CA $2,417, price is now CA $1,535 per person
CA $1,535
per person
May 12 - May 18
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
The room was clean, and the staff were so nice and helpful!
Reviewed on Feb 20, 2026
Legacy Trail Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Mar 1 to Mar 2
CA $154
CA $190 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (5,046 reviews)
Good staff nice room good service price was great
Reviewed on Feb 26, 2026
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $174 per night from Mar 1 to Mar 2
CA $174
CA $197 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (2,293 reviews)
Fun, novel setting!
Reviewed on Feb 26, 2026
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
The price is CA $365 per night from Mar 4 to Mar 5
CA $365
CA $448 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (5,326 reviews)
excellent staff very kind! beach is more than 100 yards away and no dresser drawers or hooks for wet swim suits or towels in the rooms. the pool area is beautiful and very well kept
Reviewed on Feb 25, 2026
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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- Adults Only Resorts & in Bee Ridge
- All Inclusive Resorts and in Bee Ridge
- Beach Hotel Hotels in Bee Ridge
- Pet-Friendly Hotels in Bee Ridge
- Bee Ridge Hotels
- Coral Cove Hotels
- Hotels near Crescent Beach
- Adults Only Resorts & in Gulf Gate Estates
- All Inclusive Resorts and in Gulf Gate Estates
- Beach Hotel Hotels in Gulf Gate Estates
- Cheap Hotels in Gulf Gate Estates
- Hotels & Resorts for Couples in Gulf Gate Estates
- Golf Hotels in Gulf Gate Estates
- Honeymoon Resorts and in Gulf Gate Estates
- Lgbt Friendly Hotels in Gulf Gate Estates
- Luxury Hotels in Gulf Gate Estates
- Oceanfront Hotels in Gulf Gate Estates
- Pet-Friendly Hotels in Gulf Gate Estates
- Waterpark Hotels in Gulf Gate Estates
- Hotel Wedding Venues Hotels in Gulf Gate Estates
- Gulf Gate Estates Hotels
- Hotels near Historic Spanish Point
- B&B in Osprey
- Guest Houses in Osprey
- Adults Only Resorts & in Osprey
- Beach Hotel Hotels in Osprey
- Boutique Hotels in Osprey
- Lake Hotels in Osprey
- Mountain Hotels in Osprey
- Oceanfront Hotels in Osprey
- Osprey Hotels
- Lodges in Osprey
- Vacation Homes in Osprey
- Resorts in Osprey
- Apartments in Osprey Village
- Cottages in Osprey Village
- Guest Houses in Osprey Village
- Osprey Village Hotels
- Resorts in Osprey Village
- Villas in Osprey Village
- All Inclusive Resorts and in Palmer Ranch
- Beach Hotel Hotels in Palmer Ranch
- Cheap Hotels in Palmer Ranch
- Golf Hotels in Palmer Ranch
- Lgbt Friendly Hotels in Palmer Ranch
- Luxury Hotels in Palmer Ranch
- Oceanfront Hotels in Palmer Ranch
- Spa Hotels in Palmer Ranch
- Palmer Ranch Hotels
- Hotels near Point of Rocks
- Hotels near Sarasota Square
- South Gate Ridge Hotels
- Hotels near Stoneybrook Golf & Country Club
- Hotels near The Oaks Club
- Hotels near Turtle Beach
- Beach Hotel Hotels in Vamo
- Boutique Hotels in Vamo
- Oceanfront Hotels in Vamo
- Vamo Hotels
- Bent Tree Country Club
- Ca’ d’Zan
- Casey Key Vacations
- Crescent Beach
- Ed Smith Stadium
- Jim Neville Marine Preserve
- John and Mable Ringling Museum of Art
- Lido Beach
- Lido Key Vacations
- Mall at University Town Center
- Marie Selby Botanical Gardens
- Mote Marine Laboratory & Aquarium
- Nathan Benderson Park
- Nokomis Beach
- North Jetty Beach
- Oscar Scherer State Park
- Visit Osprey Village
- Sarasota BayWalk
- Visit Bee Ridge
- Sarasota Classic Car Museum
- Sarasota Commons Shopping Center
- Visit Gulf Gate Estates
- Sarasota Jungle Gardens
- Sarasota Opera House
- Visit Palmer Ranch
- Visit Vamo
- Sarasota Vacations
- Siesta Key Beach
- Siesta Key Vacations
- St. Armands Circle
- St. Boniface Episcopal Church Labyrinth
- Stoneybrook Golf & Country Club
- Van Wezel Performing Arts Hall
- Venice Beach
- Venice Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
