Legacy Trail Vacation Packages

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Top Legacy Trail vacation package deals

Price found within the past 48 hours. Click for updated prices.
FUSION Resort Waterfront Suites
3.5-star property

FUSION Resort Waterfront Suites

9.2/10 Wonderful! (1,173 reviews)

Jun 24 - Jun 29

5 night stay

Boston (BOS) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,061, price is now $715 per person
$715
per person
found 1 day ago
Room wasn’t ready when we arrived, we had to wait 45 minutes. The front desk lady didn’t have a name tag so I couldn’t addressed her properly. She didn’t have good communication skills. Richard was awesome he had to take over and helped her. Other than that was a great clean place to stay.

Reviewed on Jul 2, 2024

Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (510 reviews)

Aug 3 - Aug 8

5 night stay

Boston (BOS) to Tampa (TPA)

Delta • Coach

Tampa (TPA) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,333, price is now $839 per person
$839
per person
found 1 day ago
Extremely clean. Friendly, helpful staff that went above and beyond. I traveled with my teenage daughter and her friend and we never once felt unsafe. I was fine using the free trolley transportation up and down the island, but the girls talked me into renting a golf cart. That did provide more freedom for our short time there. The resort has golf carts for rent. We will definitely be back!

Reviewed on Aug 10, 2025

Mar Bay Motel &Suites
2.0-star property

Mar Bay Motel &Suites

8.6/10 Excellent! (78 reviews)

Jul 20 - Jul 27

7 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop • Coach

Tampa (TPA) to Newark Liberty Intl. Airport (EWR)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,194, price is now $754 per person
$754
per person
found 15 hours ago
Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,219 reviews)

Jun 24 - Jun 29

5 night stay

Boston (BOS) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,522, price is now $987 per person
$987
per person
found 1 day ago
Could not be happier. Staff were attentive, welcoming and super knowledgeable. Property was pristine, amazing amazing location and tons of onsite activities and luxuries. If we could have given ten stars we would have.

Reviewed on Apr 10, 2026

Crystal Palms Beach Resort
3.5-star property

Crystal Palms Beach Resort

Sunshine Beach
8.8/10 Excellent! (2,376 reviews)

Jun 24 - Jun 29

5 night stay

Boston (BOS) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,087, price is now $743 per person
$743
per person
found 1 day ago
Room was very well laid out All pf the amenities needed Excellent balcony view Covered parking Close to the beach Room was a bit dirty Property was run down and in need of freshening up Overall it was a 4 out of 5 experience and I'd go back

Reviewed on Sep 26, 2022

Top rated hotels for your Legacy Trail vacation package

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Free Cancellation
Reserve now, pay when you stay
11.51 mi from city center
$106 nightly
The price is $120 total per night
$120 total
Jun 7 - Jun 8
Total with taxes and fees
At Kompose Boutique Hotel, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 5.35 per night. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. Additional amenities include a hot tub, a 24-hour business center, and a microwave in a common area.
Pool
Hot Tub
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
22.55 mi from city center
$163 nightly
The price is $185 total per night
$185 total
May 28 - May 29
Total with taxes and fees
At Compass Hotel by Margaritaville Anna Maria Sound, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and securing valuables. Additional amenities include conference space, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Free Cancellation
11.04 mi from city center
$75 nightly
The price is $85 total per night
$85 total
May 31 - Jun 1
Total with taxes and fees
Golden Host Resort - Sarasota features an outdoor pool, free WiFi in public areas, and coffee in a common area. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a library, express check-out, and free newspapers.
Pool
Parking included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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