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Legacy Trail Vacation Packages

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A wooden pathway surrounded by dense greenery and trees.

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.

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5

Save 100% on your flight

Price was $412, price is now $241 per person

$241

per person

Sep 23 - Sep 26

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.

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,271, price is now $718 per person

$718

per person

Oct 11 - Oct 17

found 11 hours 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.

First time staying here and we loved it. Pet fee was a little steep.

Reviewed on Jul 28, 2026

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $827, price is now $484 per person

$484

per person

Sep 23 - Sep 26

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 Coquina Beach and Bean Point Beach are located nearby.

Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!

Reviewed on Jul 26, 2026

The Westin Sarasota

4 out of 5

Save 100% on your flight

Price was $1,368, price is now $839 per person

$839

per person

Oct 3 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.

The shuttle was so continent! Nice place to stay would go again.

Reviewed on Jul 28, 2026

CW Hotel

4 out of 5

Save 100% on your flight

Price was $666, price is now $430 per person

$430

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Thank you for giving us such a wonderful vacation. Everything was excellent—the staff were kind and friendly, and the food at the restaurant was delicious. What we appreciated most was the cleanliness. We will definitely return for another holiday. Thank you so much.

Reviewed on Jul 28, 2026

voco Sarasota by IHG

3.5 out of 5

Save 100% on your flight

Price was $1,118, price is now $722 per person

$722

per person

Oct 3 - Oct 11

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 St. Armands Circle and Lido Beach are located nearby.

Saddlebrook Resort

4 out of 5

Save 100% on your flight

Price was $426, price is now $275 per person

$275

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.

Resort Sixty-Six

2.5 out of 5

Save 100% on your flight

Price was $1,182, price is now $789 per person

$789

per person

Oct 17 - Oct 24

found 20 hours ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bean Point Beach and Coquina Beach are located nearby.