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Legacy Trail Vacation Packages

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A paved road flanked by dense tropical vegetation.

Legacy Trail
Florida
United States of America
North America
Hotwire.com

Legacy Trail Flight + Hotel Packages

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

Legacy Hotel at IMG Academy

4 out of 5

Price was $1,006, price is now $603 per person

$603

per person

Jan 13 - Jan 17

found 1 day 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 Golf Academy are located nearby.

Ocean Club Treasure Island Hotel

4 out of 5

Price was $1,099, price is now $630 per person

$630

per person

Jan 11 - Jan 16

found 1 day ago

Roundtrip 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.

Nice property, clean pool. Units were not sound roof at all, you could hear every little noise from each room and other units, but it did not ruin our time there.

Reviewed on Nov 10, 2026

Cedar Cove Resort and Cottages

3 out of 5

Price was $1,336, price is now $793 per person

$793

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

What a treat for us Minnesotans!!! Special place to stay. Clean, comfy, and cozy! We stayed in the Violet Cottage. Staff allowed us to hang for a bit on the beach (plus parking for our rental) after check-out. There is even a shower available for this exact purpose, which is extra handy and appreciated. Thank you! We hope to be back some day!

Reviewed on Nov 9, 2026

voco Sarasota by IHG

3.5 out of 5

Price was $1,057, price is now $654 per person

$654

per person

Feb 3 - Feb 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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 St. Armands Circle and Lido Beach are located nearby.

Crystal Palms Beach Resort

3.5 out of 5

Save 100% on your flight

Price was $1,207, price is now $751 per person

$751

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating

Reviewed on Nov 7, 2026

The Roth Hotel

2 out of 5

Price was $1,349, price is now $855 per person

$855

per person

Jan 24 - Jan 31

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Treasure Island. Enjoy free WiFi, free parking, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Sunset Beach Pavilion are located nearby.

Truly a treasure!!! Don’t miss the opportunity to stay here. Love the proximity to the beach. The dock was so tranquil and great for sipping coffee in the mornings and my son loved to fish and watch for dolphins & manatees!

Reviewed on Sep 12, 2026

Sunset Vistas Two Bedroom Beachfront Suites

3.5 out of 5

Price was $1,082, price is now $688 per person

$688

per person

Jan 11 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach aparthotel in Treasure Island. Enjoy 2 outdoor pools, a beach locale, and 2 hot tubs. 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.

See my yelp review

Reviewed on Nov 10, 2026

The Knickerbocker by Delphius

3 out of 5

Price was $2,608, price is now $1,666 per person

$1,666

per person

Jan 11 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly B&B in Tampa. Enjoy free WiFi, free parking, and 3 meeting rooms. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.

Legacy Trail Vacation Packages 3-4 Night Stays

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

Ocean Club Treasure Island Hotel

4 out of 5

Sunshine Beach

Save 100% on your flight

Price was $894, price is now $534 per person

$534

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Cedar Cove Resort and Cottages

3 out of 5

Price was $1,336, price is now $793 per person

$793

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)