
Legacy Trail Vacations from $811
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The Latest Legacy Trail vacation packages
Price found within the past 48 hours. Click for updated prices.


The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Price was $2,479, price is now $1,292 per person
$1,292
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
9.6/10 Exceptional! (292 reviews)
Really loved our stay! We had a 3 bedroom apartment with plenty of space and modern amenities. 3 gorgeous walk in showers, enormous bathtub. The complimentary breakfast was very useful with small children. Pool and beach access were great. Complimentary paddle boards and kayaks made it really fun. Location is nice as there is a Breeze shuttle stop at the end of the road but the property itself is in a very quiet location. The sunset was fabulous. We will be back!
Reviewed on Oct 25, 2025

Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $2,047, price is now $1,152 per person
$1,152
per person
Jan 26 - Feb 2
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
We had a wonderful stay! The location was fantastic, within walking distance to plenty of restaurants and food options. The views of the ocean were stunning, especially during sunrise and sunset. The beds were very comfortable, and it was super convenient having a full kitchen with all the necessary appliances and white goods.
There was a bit of confusion and upset on arrival regarding the resort fee and taxes, which ended up being higher than what was confirmed by Expedia, but aside from that, everything else was great. Overall, a really enjoyable holiday with beautiful memories made.
Reviewed on Nov 5, 2025

Landing Apartments near North Fort Myers
Hancock
Save 100% on your flight
Price was $1,663, price is now $1,003 per person
$1,003
per person
Jan 12 - Jan 19
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.4/10 Exceptional! (40 reviews)
The kitchen was fully equipped for cooking. Safe parking. Bed blankets and pillows were excellent.
Reviewed on Nov 3, 2025

Innisbrook Resort
Save 100% on your flight
Price was $2,450, price is now $1,478 per person
$1,478
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,009 reviews)
Property was very clean and quiet. Loved the lap pool. We will be back!
Reviewed on Oct 23, 2025
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Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $109 total per night from Nov 18 to Nov 19
$109 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (4,584 reviews)
Staff is professional and courteous, the rooms are always clean and the gated lot is always secure. It’s my first choice for staying in Sarasota
Reviewed on Nov 5, 2025

Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $204 total per night from Nov 9 to Nov 10
$204 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (5,071 reviews)
We cannot express enough how much we love staying at Tropical Beach Resorts The rooms are fantastic, staff is welcoming, friendly, and helpful.
Reviewed on Nov 2, 2025

Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl, Sarasota, FL
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $126 total per night from Nov 12 to Nov 13
$126 total
Nov 12 - Nov 13
Total with taxes and fees
8.2/10 Very Good! (1,811 reviews)
Room was good, although the property had some safety issues
Reviewed on Nov 3, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















