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.
voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

Central Sarasota
9/10 Wonderful! (1,012 reviews)

May 14 - May 19

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 $896, price is now $543 per person
$543
per person
found 1 day ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.

Reviewed on Jun 30, 2024

The Westin Sarasota
4.0-star property

The Westin Sarasota

Central Sarasota
9/10 Wonderful! (1,193 reviews)

Jun 2 - Jun 7

5 night stay

Detroit (DTW) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,485, price is now $905 per person
$905
per person
found 1 day ago
$50 per valet without other option is too high

Reviewed on Sep 8, 2025

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

Sunshine Beach
9.6/10 Exceptional! (846 reviews)

May 5 - May 11

6 night stay

Boston (BOS) to Tampa (TPA)

Delta • Coach

Tampa (TPA) to Boston (BOS)

American Airlines • Coach
Price was $2,036, price is now $1,311 per person
$1,311
per person
found 1 day ago
Great spot, had a great time

Reviewed on Dec 4, 2025

Bay Palms Waterfront Resort - Hotel and Marina
3.0-star property

Bay Palms Waterfront Resort - Hotel and Marina

Belle Vista
8.4/10 Very Good! (525 reviews)

Jun 7 - Jun 14

7 night stay

Detroit (DTW) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $934, price is now $625 per person
$625
per person
found 21 hours ago
This is the cutest little place. Booked at the last minute. Close enough to walk to for food. The hotel had a happy hour as soon as we checked in and there was also a hotel bar on the beach. I would definitely recommend this hotel. Newly rennovated. I could hear the ocean from my room.

Reviewed on Mar 28, 2022

The Sarasota Modern, a Tribute Portfolio Hotel
4.0-star property

The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota
8.2/10 Very Good! (532 reviews)

Jun 8 - Jun 12

4 night stay

Detroit (DTW) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,072, price is now $742 per person
$742
per person
found 1 day ago
The only thing we didn’t like was being charged 30.00 a day to park. Also bathrooms very dark as were the black hallways.

Reviewed on Nov 12, 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
$121 nightly
The price is $137 total per night
$137 total
Apr 4 - Apr 5
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.
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
$79 nightly
The price is $89 total per night
$89 total
Apr 26 - Apr 27
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.
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Free Cancellation
Reserve now, pay when you stay
22.55 mi from city center
$203 nightly
The price is $229 total per night
$229 total
Apr 12 - Apr 13
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 securing valuables, luggage storage, and concierge services. Additional amenities include conference space, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
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