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.
The Westin Sarasota
4.0-star property

The Westin Sarasota

Central Sarasota
9/10 Wonderful! (1,196 reviews)

Aug 6 - Aug 11

5 night stay

Baltimore (BWI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $775, price is now $505 per person
$505
per person
found 5 hours ago
$50 per valet without other option is too high

Reviewed on Sep 8, 2025

Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (510 reviews)

Aug 8 - Aug 15

7 night stay

Baltimore (BWI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,704, price is now $962 per person
$962
per person
found 18 hours 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

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

Sunshine Beach
9.6/10 Exceptional! (932 reviews)

Jul 25 - Aug 1

7 night stay

Baltimore (BWI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,832, price is now $1,046 per person
$1,046
per person
found 1 day ago
This place is gorgeous and I highly recommend. I gave 4 stars because the guy working the desk was not very smart. He overcharged us by $200. He gave me the wrong WiFi password. I hope I get my money back. Otherwise it was a beautiful stay.

Reviewed on May 12, 2026

Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,219 reviews)

Jul 25 - Aug 1

7 night stay

Baltimore (BWI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,953, price is now $1,205 per person
$1,205
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

Pelican Pointe Clearwater Beach Hotel
2.5-star property

Pelican Pointe Clearwater Beach Hotel

9/10 Wonderful! (1,015 reviews)

Jul 25 - Aug 1

7 night stay

Baltimore (BWI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,088, price is now $702 per person
$702
per person
found 1 day ago
Every thing of the above was good

Reviewed on Nov 26, 2025

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
$101 nightly
The price is $114 total per night
$114 total
May 20 - May 21
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
Free Cancellation
Reserve now, pay when you stay
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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