Search Deals onLegacy Trail Vacation Packages
Legacy Trail Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Price was $549, price is now $298 per person
$298
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Everything here was fantastic!! I don’t want to tell everyone how great it is because I want it all to myself!! It was the cleanest, friendliest place that I’ve stayed. If I could give 10 stars I would!! To all the employees at the Chart House you are great!!
Reviewed on Aug 25, 2026
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $1,170, price is now $660 per person
$660
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
The beach view was great. Just steps away. Our room was very clean and smelled refreshing when entering. Staff was very helpful. We will be back
Reviewed on Aug 22, 2026
CW Resort
Save 100% on your flight
Price was $490, price is now $309 per person
$309
per person
Nov 13 - Nov 15
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
I didn’t like the hotel food
Reviewed on Aug 24, 2026
Legacy Hotel at IMG Academy
Save 100% on your flight
Price was $491, price is now $314 per person
$314
per person
Oct 22 - Oct 25
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and IMG Bollettieri Tennis Academy are located nearby.
Stylish Treasure Island Escape
Save 100% on your flight
Price was $7,902, price is now $5,066 per person
$5,066
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Stay at this apartment in Treasure Island. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $570, price is now $367 per person
$367
per person
Oct 22 - Oct 25
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
SkyBeach Resort
Save 100% on your flight
Price was $900, price is now $591 per person
$591
per person
Nov 5 - Nov 10
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Tropicana Field and Salvador Dali Museum are located nearby.
Staff were amazing, very nice amenities. 10-14 mins from downtown. Rooms were nice. Will return soon.
Reviewed on Aug 24, 2026
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $695, price is now $457 per person
$457
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
super clean and confortable
Reviewed on Aug 24, 2026
Legacy Trail Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Legacy Trail Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Aug 27 - Sun, Aug 30
PSM
Portsmouth Intl.
PGD
Punta Gorda Airport
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Tue, Nov 10 - Wed, Nov 18
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 23 hours ago
$217
Roundtrip
found 23 hours ago
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Tue, Nov 3 - Tue, Nov 10
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$229 Roundtrip, found 1 hour ago
$229
Roundtrip
found 1 hour ago
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