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Legacy Trail Vacation Packages

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Legacy Trail Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $509, price is now $352 per person
$352
per person
Jun 1 - Jun 4
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,671, price is now $1,071 per person
$1,071
per person
Jun 21 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $863, price is now $555 per person
$555
per person
Jul 13 - Jul 17
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $553, price is now $367 per person
$367
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Safety Harbor Waterfront Park are located nearby.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $616, price is now $413 per person
$413
per person
Jun 1 - Jun 4
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 breakfast (surcharge). Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
East Gulf Dockside Beach Homes

East Gulf Dockside Beach Homes

2.5 out of 5
Save 100% on your flight
Price was $1,982, price is now $1,333 per person
$1,333
per person
Jul 3 - Jul 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Book a stay at this beach apartment in Indian Rocks Beach. Enjoy free WiFi, free parking, and 6 beach bars. Popular attractions St. Petersburg - Clearwater Beaches and Splash Harbour Water Park are located nearby.
The Avalon Club

The Avalon Club

4 out of 5
Price was $2,055, price is now $1,390 per person
$1,390
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,191, price is now $810 per person
$810
per person
Jun 12 - Jun 15
found 1 day 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.

Legacy Trail Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $553, price is now $367 per person
$367
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,671, price is now $1,071 per person
$1,071
per person
Jun 21 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $863, price is now $555 per person
$555
per person
Jul 13 - Jul 17
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $616, price is now $413 per person
$413
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)

Legacy Trail Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $908, price is now $578 per person
$578
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,803, price is now $1,726 per person
$1,726
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,995, price is now $1,293 per person
$1,293
per person
Jun 3 - Jun 8
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,246, price is now $808 per person
$808
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, May 12 - Sat, May 16
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, May 12 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, May 16, priced at $197 found 2 days ago
JetBlue Airways
Sat, May 30 - Wed, Jun 3
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 30 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Wed, Jun 3, priced at $202 found 1 day ago
Delta
Mon, May 18 - Tue, Jun 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 9 hours ago
$207
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, May 18 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Jun 2, priced at $207 found 9 hours ago
Delta
Thu, Jul 9 - Sat, Jul 11
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$239 Roundtrip, found 10 hours ago
$239
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Jul 9 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sat, Jul 11, priced at $239 found 10 hours ago