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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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $849, price is now $385 per person
$385
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $1,342, price is now $602 per person
$602
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this spa vacation home in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Seminole Hard Rock Casino Tampa and Port of Tampa are located nearby.
Family Home Tampa

Family Home Tampa

2 out of 5
Save 100% on your flight
Price was $1,220, price is now $629 per person
$629
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this guesthouse in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Busch Gardens Tampa Bay and Raymond James Stadium are located nearby.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $824, price is now $427 per person
$427
per person
Mar 2 - Mar 8
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Chi Chi Rodriguez Golf Club are located nearby.
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Price was $2,929, price is now $1,564 per person
$1,564
per person
Mar 6 - Mar 11
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Sarasota (SRQ)
Book a stay at this beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $988, price is now $563 per person
$563
per person
Mar 6 - Mar 11
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, a private beach, and a marina. Popular attractions Salvador Dali Museum and Fort De Soto Park are located nearby.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,307, price is now $1,339 per person
$1,339
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $2,694, price is now $1,582 per person
$1,582
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Legacy Trail Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Save 100% on your flight
Price was $669, price is now $380 per person
$380
per person
Feb 5 - Feb 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $900, price is now $415 per person
$415
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,203, price is now $1,299 per person
$1,299
per person
Feb 22 - Feb 26
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $646, price is now $385 per person
$385
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

Legacy Trail Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $849, price is now $385 per person
$385
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $1,342, price is now $602 per person
$602
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $906, price is now $441 per person
$441
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Save 100% on your flight
Price was $1,220, price is now $629 per person
$629
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

Top Flight Deals

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

United
Wed, Jan 21 - Wed, Jan 28
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Jan 21 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Wed, Jan 28, priced at $127 found 1 hour ago
JetBlue Airways
Wed, Jan 7 - Thu, Jan 15
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$146 Roundtrip, just found
$146
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Jan 7 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Thu, Jan 15, priced at $146 just found
JetBlue Airways
Mon, Jan 19 - Fri, Jan 23
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$149 Roundtrip, found 6 hours ago
$149
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Mon, Jan 19 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Jan 23, priced at $149 found 6 hours ago
Frontier Airlines
Thu, Feb 12 - Thu, Feb 19
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Philadelphia Intl. to Sarasota-Bradenton Intl., returning Thu, Feb 19, priced at $153 found 20 hours ago