Book Hotels in Legacy Trail, FL

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight
Dec 8 - Dec 9
Tomorrow
Dec 9 - Dec 10
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Legacy Trail hotels

Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $192 total per night from Dec 10 to Dec 11
$192 total
Dec 10 - Dec 11
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and ...
Friendly and knowledgeable staff, clean room, convenient location.

Reviewed on Dec 3, 2025

Opens in a new windowCarlisle Inn
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $200 total per night from Dec 15 to Dec 16
$200 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free ...
Wouldn't change anything.

Reviewed on Dec 5, 2025

Opens in a new windowCompass Hotel by Margaritaville Anna Maria Sound
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $175 total per night from Dec 9 to Dec 10
$175 total
Dec 9 - Dec 10
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A garden, a library, and a picnic area ...
The room was clean, they provided fresh towels each day, and they were accommodating. Our only complaints were the shades on the windows did not have tilt wands to adjust the blinds, and the kitchen utensils were left to be desired (no spatula, corkscrew, or baking dish were ones we noticed) and ...

Reviewed on Dec 5, 2025

Opens in a new windowTropical Beach Resorts
Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

3 out of 5
950 University Parkway Sarasota FL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $121 total per night from Dec 21 to Dec 22
$121 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Very conveniente location for the airport with shuttle transportation. Not much of a choice for dining if you do not want to go out of the hotel. Adequate breakfast included. Overall stay satisfactory.

Reviewed on Dec 6, 2025

Opens in a new windowHyatt Place Sarasota/Bradenton Airport
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Dec 9 to Dec 10
$102 total
Dec 9 - Dec 10
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll ...
I had a short but amazing stay with my kids. The family suite was perfect. I’m looking forward to my next visit.

Reviewed on Dec 7, 2025

Opens in a new windowKompose Boutique Hotel
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
6772 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $187 total per night from Dec 9 to Dec 10
$187 total
Dec 9 - Dec 10
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
Clean room, snd friendly staff. Great location

Reviewed on Dec 1, 2025

Opens in a new windowCaptiva Beach Resort
Lido Beach Resort

Lido Beach Resort

4 out of 5
700 Benjamin Franklin Dr Sarasota FL
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $338 total per night from Dec 14 to Dec 15
$338 total
Dec 14 - Dec 15
Total with taxes and fees
This smoke-free resort features a private beach, 2 outdoor pools, and a restaurant. Spend a day at the beach surfing, or relax with beach cabanas and sun loungers. ...
Excellent service, everything was spotless. Staff was ready to help and very courteous

Reviewed on Dec 6, 2025

Opens in a new windowLido Beach Resort
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
1735 Stickney Point Rd Sarasota FL
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $170 total per night from Dec 9 to Dec 10
$170 total
Dec 9 - Dec 10
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a picnic area ...
Room was spotlessly clean and nicely upgraded. 5 min drive to Siesta Beach. Would definitely stay there again. Pool updated and beach towels and chairs provided for free for your trip to the beach.

Reviewed on Dec 4, 2025

Opens in a new windowHibiscus Suites - Gateway to Siesta Key
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
$80 nightly
The price is $91 total per night from Dec 9 to Dec 10
$91 total
Dec 9 - Dec 10
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, ...
Everything Was Wonderful

Reviewed on Dec 2, 2025

Opens in a new windowGolden Host Resort - Sarasota
Don't see what you're looking for?
See all available properties in Legacy Trail
View all properties
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.

Recent Legacy Trail hotel reviews by fellow wanderers

Kompose Boutique Hotel

Kompose Boutique Hotel

5 out of 5
Posted 21 hours ago
Travelocity Verified Review
"I had a short but amazing stay with my kids. The family suite was perfect. I’m looking forward to my next visit. "
A verified traveler stayed at Kompose Boutique Hotel
Kompose Boutique Hotel

Explore More Ways to Travel with Travelocity