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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.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $622, price is now $389 per person
$389
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Clean rooms and staff was perfect very friendly

Reviewed on Oct 11, 2026

CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,431, price is now $906 per person
$906
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Property was very nice but living area of room not very comfortable. Small love seat & chair to watch tv wasn't comfortable.

Reviewed on Oct 12, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,821, price is now $1,216 per person
$1,216
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,085, price is now $733 per person
$733
per person
Dec 3 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Resort Sixty-Six

Resort Sixty-Six

2.5 out of 5
Save 100% on your flight
Price was $1,458, price is now $1,010 per person
$1,010
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
Great property well maintained. Staff is helpful and welcoming.

Reviewed on Oct 10, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $731, price is now $510 per person
$510
per person
Dec 22 - Dec 26
found 18 hours 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.
Pretty new

Reviewed on Oct 11, 2026

Landing Beautiful 2bd, Gym

Landing Beautiful 2bd, Gym

3 out of 5
Save 100% on your flight
Price was $1,151, price is now $805 per person
$805
per person
Jan 4 - Jan 9
found 24 hours ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Stay at this apartment in Palmetto. Enjoy free parking, an outdoor pool, and a 24-hour fitness center. Popular attractions Palmetto Historical Park and Manatee County Agricultural Museum are located nearby.

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $744, price is now $525 per person
$525
per person
Dec 22 - Dec 26
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
No complaints at all. Everything and everyone was perfect! We would definitely stay here again.

Reviewed on Oct 11, 2026

Legacy Trail Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $607, price is now $355 per person
$355
per person
Dec 3 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,821, price is now $1,216 per person
$1,216
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $844, price is now $568 per person
$568
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,085, price is now $733 per person
$733
per person
Dec 3 - Dec 7
found 24 hours 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.
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,431, price is now $906 per person
$906
per person
Dec 12 - Dec 19
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 $1,706, price is now $937 per person
$937
per person
Dec 12 - Dec 19
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 $3,611, price is now $2,226 per person
$2,226
per person
Jan 4 - Jan 9
found 24 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Sunshine Beach
Save 100% on your flight
Price was $6,552, price is now $4,317 per person
$4,317
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Tampa (TPA)

Top Flight Deals

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

Allegiant Air
Fri, Dec 4 - Thu, Dec 10
PSM
Portsmouth Intl.
PGD
Punta Gorda Airport
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Dec 4 from Portsmouth Intl. to Punta Gorda Airport, returning Thu, Dec 10, priced at $144 found 2 days ago
Delta
Wed, Dec 2 - Sat, Dec 12
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 5 hours ago
$199
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Dec 2 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 12, priced at $199 found 5 hours ago
Delta
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Delta flight, departing Tue, Jan 19 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Feb 2, priced at $199 just found
Delta
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Delta flight, departing Tue, Jan 5 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 9, priced at $199 just found