Title: Legacy Trail Vacation Packages 2026 from $854 | Expedia.com [Legacy Trail Travel Guide](https://expedia.com/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.com/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Vacation Rentals in Legacy Trail](https://expedia.com/Legacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[Flights to Legacy Trail](https://expedia.com/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Car Rentals in Legacy Trail](https://expedia.com/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Legacy Trail Vacations from $854 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## The Latest Legacy Trail vacation packages Price found within the past 48 hours. Click for updated prices. ![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/3e4355d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Club Treasure Island Hotel Sunshine Beach Save 100% on your flight $854 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.6/10 Exceptional! (712 reviews) Whole property was AMAZING!! Reviewed on Feb 15, 2026 ![The Don CeSar](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/2e9ef8e3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Don CeSar Save 100% on your flight $1,236 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9/10 Wonderful! (1,044 reviews) Great stay! Plan on the beach. Alternate to the pool to cool off. Will be back. Beautiful! Reviewed on Feb 14, 2026 ![The Residences at Siesta Key Beach by Hyatt Vacation Club](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/a5a3d5ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Residences at Siesta Key Beach by Hyatt Vacation Club South Village $1,922 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip non-stop flight included Boston (BOS) to Sarasota (SRQ) 9.6/10 Exceptional! (294 reviews) The view was fantastic and staff went out of their way to make your visit enjoyable! Reviewed on Feb 3, 2026 ![FUSION Resort Waterfront Suites](https://images.trvl-media.com/lodging/37000000/36180000/36176500/36176495/bea713d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### FUSION Resort Waterfront Suites Save 100% on your flight $873 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.2/10 Wonderful! (1,097 reviews) Very clean and yes I would come again Reviewed on Feb 13, 2026 ![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/0a89d66d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cedar Cove Resort and Cottages $1,279 per person Apr 9 - Apr 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Sarasota (SRQ) 9.2/10 Wonderful! (480 reviews) Everything was perfect cant wait to go back Reviewed on Feb 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Legacy Trail [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248621532652531) ## Legacy Trail Hotel Deals ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Kompose Boutique Hotel 965 University Pkwy Sarasota FL Fully refundableReserve now, pay when you stay $99 nightly $112 total Feb 16 - Feb 17 Total with taxes and fees 9/10 Wonderful! (4,981 reviews) Staff was great…room was spotless. Breakfast was great. Reviewed on Feb 12, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=38215316&PinnedHotelID=38215316&HadPinnedHotel=true®ionId=553248621532652531) ![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Golden Host Resort - Sarasota 4675 N Tamiami Trl Sarasota FL Fully refundable $115 nightly $130 total Feb 16 - Feb 17 Total with taxes and fees 8.4/10 Very Good! (2,268 reviews) Nice staff Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=21331&PinnedHotelID=21331&HadPinnedHotel=true®ionId=553248621532652531) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Tropical Beach Resorts 6717 Sara Sea Circle Siesta Key FL Fully refundableReserve now, pay when you stay $349 nightly $395 total Feb 18 - Feb 19 Total with taxes and fees 9.2/10 Wonderful! (5,290 reviews) It was perfect location it was beautiful clean hotel I would definitely at least stay there again Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F18%2F2026&endDate=2%2F19%2F2026&selected=1240909&PinnedHotelID=1240909&HadPinnedHotel=true®ionId=553248621532652531) [See all 17,407 properties in Legacy Trail](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F16%2F2026&endDate=2%2F17%2F2026®ionId=553248621532652531) 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. ## Find the Best Legacy Trail Vacation Packages ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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