Legacy Trail Vacation Packages 2026 from $590

Legacy Trail flight + hotel vacation packages

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$590

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,074

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

The Avalon Club

Save 100% on your flight

$948

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$1,766

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

The Hotel Zamora

Save 100% on your flight

$593

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A marina, a 24-hour gym, and a restaurant are all featured at this Mediterranean hotel. Unwind with a drink at one of the 3 bars/lounges and enjoy freebies like WiFi in public areas and a beach shuttle. You'll appreciate the outdoor pool, poolside bar, and concierge services.