
Legacy Trail Vacations from ₩751,110
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Legacy Trail Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Saddlebrook Resort
Wesley Chapel South
Price was ₩932,426, price is now ₩751,110 per person
₩751,110
per person
Feb 20 - Feb 22
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
No reviews
Condition of the rooms are not great. I suffer from allergies and asthma. The air quality in the room was horrible. Carpeting and drapes being the culprit but also the air vents haven’t been cleaned hence my health from pollutant triggers. Staff are friendly, courteous, pleasant and very helpful. The sliding door in the bedroom does not lock. The windows slide open yet falls off track and is crooked when opened. Not an issue at first but eyebrow raised when front desk reminds me that it’s a renovated room.
Reviewed on Jan 17, 2026

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Beach Park
Price was ₩1,068,169, price is now ₩862,464 per person
₩862,464
per person
Feb 20 - Feb 22
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
8.6/10 Excellent! (1,751 reviews)
Staff were friendly, room was fine.
I requested pick up at the airport from the free shuttle via Expedia messaging and directly with the hotel messaging . No answer received and no shuttle. I had to take an Uber taxi.
Reviewed on Jan 18, 2026

Hampton Inn Tampa Downtown Channel District
Downtown Tampa
Price was ₩1,254,875, price is now ₩1,017,495 per person
₩1,017,495
per person
Feb 20 - Feb 22
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
9.4/10 Exceptional! (2,021 reviews)
Clean room, quick check in and courteous staff. Perfect stay the night before a cruise and super close to port with a shuttle and breakfast
Reviewed on Jan 19, 2026

Hotel Tampa Riverwalk
Downtown Tampa
Price was ₩1,351,661, price is now ₩1,111,628 per person
₩1,111,628
per person
Feb 20 - Feb 22
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
Helpful and friendly staff. Rooms are clean and have all the necessary items. I was upgraded to the room with the river view and king bed, which I appreciated! Breakfast was not included but the daily amenities fee of $25 that is applied over and above what the room costs covers most of the breakfast cost.
Only real negative is that the hotel decor looks a little dated especially the carpets, which could use a refresh.
Reviewed on Jan 18, 2026

Hotel South Tampa & Suites
Virginia Park
Price was ₩1,104,964, price is now ₩918,311 per person
₩918,311
per person
Feb 20 - Feb 22
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
8.6/10 Excellent! (1,584 reviews)
Fill the room with towels and make the bed daily would be appreciated.
Reviewed on Jan 17, 2026
Find the Best Legacy Trail Vacation Packages
Legacy Trail Hotel Deals

Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is ₩122,236 per night from Jan 20 to Jan 21
₩122,236
₩138,136 total
Jan 20 - Jan 21
includes taxes & fees
8.4/10 Very Good! (2,210 reviews)
The room was spacious and clean! Had a great view of the pool and a balcony! The property looks older but the rooms are remodeled nicely! Will for sure stay again. The staff was incredible helpful and friendly!
Reviewed on Jan 13, 2026

Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
The price is ₩249,261 per night from Jan 21 to Jan 22
₩249,261
₩314,969 total
Jan 21 - Jan 22
includes taxes & fees
9.2/10 Wonderful! (5,237 reviews)
Clean room, comfy bed, adequate kitchen
Reviewed on Jan 17, 2026

Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is ₩116,147 per night from Jan 20 to Jan 21
₩116,147
₩148,913 total
Jan 20 - Jan 21
includes taxes & fees
9/10 Wonderful! (4,901 reviews)
Loved staying here! It is a really cool hotel. It was clean and comfortable for an amazing price!
Reviewed on Jan 16, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
