A paved road flanked by dense tropical vegetation.

Find hotels in Legacy Trail, FL from $76

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Dates

November 2026

December 2026

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Our total price for your stay includes taxes and fees
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Our top choices for Legacy Trail hotels

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

South Village

Christine

$179 nightly

Nov 29 - Nov 30

Total with taxes and fees

A spacious indoor area with wooden tables and chairs, large windows, and hanging plants.

2. Kompose Boutique Hotel

Sarasota

Nataly

$70 nightly

Dec 1 - Dec 2

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the water.

3. Compass Hotel by Margaritaville Anna Maria Sound

Bradenton

Luddi

$162 nightly

Nov 22 - Nov 23

Total with taxes and fees

A covered outdoor area with a pool, lounge chairs, and a wooden deck.

4. Siesta Key Palms Resort

Sarasota

Melissa

$102 nightly

Nov 15 - Nov 16

Total with taxes and fees

A pool area with lounge chairs and umbrellas, a palm tree, and a view of the ocean.

5. Lido Beach Resort

Lido Key

Bryan

$357 nightly

Dec 1 - Dec 2

Total with taxes and fees

6. Cottages at Siesta Key Inn

South Village

Richard

$112 nightly

Nov 9 - Nov 10

Total with taxes and fees

A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

7. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

kathryn

$112 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel pool area with lounge chairs and a covered seating area.

8. Carlisle Inn

Pinecraft

Susan

$165 nightly

Nov 8 - Nov 9

Total with taxes and fees

A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.

9. Siesta Key Beach Resort and Suites

Siesta Key Village

Nancy

$208 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern hotel room with a large bed, a desk, and a view of the ocean.

10. Cirque St. Armands Beachside

Lido Key

Christopher

$294 nightly

Nov 5 - Nov 6

Total with taxes and fees

A pathway flanked by palm trees and a building with a covered patio area.

11. Casey Key Resorts - Mainland

Osprey

Vito

$93 nightly

Nov 9 - Nov 10

Total with taxes and fees

An outdoor patio with a grill, white chairs, and a red umbrella.

12. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

$152 nightly

Nov 24 - Nov 25

Total with taxes and fees

A stone pathway leading through a tropical garden with palm trees and a signboard.

13. Tropical Breeze Resort

Siesta Key Village

Matthew

$138 nightly

Dec 1 - Dec 2

Total with taxes and fees

A tropical resort with a paved walkway, outdoor seating area, and a view of the beach.

14. The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Janell

An outdoor seating area with wicker furniture, a glass-top table, and a view of a lake and fountain.

15. Comfort Suites Sarasota - Siesta Key

Sarasota

Jymieka

$95 nightly

Nov 29 - Nov 30

Total with taxes and fees

A rooftop terrace with a fire feature, seating area, and a view of the city skyline.

16. The Westin Sarasota

Central Sarasota

sergio

$231 nightly

Nov 22 - Nov 23

Total with taxes and fees

A pool area with lounge chairs and palm trees, overlooking the ocean at sunset.

17. The Ritz-Carlton, Sarasota

Central Sarasota

Patricia

$717 nightly

Nov 8 - Nov 9

Total with taxes and fees

A swimming pool with a 3 ft 3 in depth marker, surrounded by lounge chairs and a covered seating area with a view of the water.

18. Turtle Beach Resort

Siesta Key

Noelle

$264 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wide beach with a clear sky and distant buildings.

19. The Capri at Siesta

South Village

Elijah

A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.

20. Inn at the Beach

Venice Island

Catherine

$175 nightly

Nov 22 - Nov 23

Total with taxes and fees

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Learn more about Legacy Trail

Cycle, walk or run the entire length or part of this popular trail. Exit onto junctions to experience a number of environments.

See all hotels in Legacy Trail

Top Legacy Trail Hotel Reviews

An outdoor seating area with a stone fire pit and cushioned sofas.

Home2 Suites Sarasota I-75 Bee Ridge, FL

Sarasota

10/10 Excellent

Marcus

A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

Best Western Plus Ambassador Suites Venice

Venice

10/10 Excellent

Erin

Kompose Boutique Hotel

Sarasota

10/10 Excellent

Steven

A rocky beach with large boulders in the foreground and a clear blue sky.

Fairfield Inn & Suites by Marriott Venice

Venice

10/10 Excellent

Mary

An outdoor patio with wicker furniture, a grill, and lush tropical plants.

Coral Pointe Sarasota, an Ascend Collection Hotel

Fruitville

10/10 Excellent

The hotel is beautifully decorated. Its very clean from the lobby to the room. The room was spotless, the beds were comfortable and they supply shampoo, conditioner and body wash in their bathrooms. The breakfast was very good. They offer hot food i.e. eggs, sausage, bacon, french toast or pancakes. They also have cereals, oatmeal, fruits and yogurt. The pool was another wonderful feature, clean and heated with plenty of chairs and tables. The staff was super friendly and very helpful. There are...

Ester

A spacious living area with a high ceiling, a sofa set, a coffee table, and a dining area with chairs.

Caretta Landing Sarasota, an Ascend Collection Hotel

Fruitville

10/10 Excellent

Laura

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

10/10 Excellent

Linda

A modern kitchen area with a wooden counter, a coffee machine, and a fruit display.

Hampton Inn Sarasota - I-75 Bee Ridge

Sarasota

10/10 Excellent

serhat

Carlisle Inn

Pinecraft

10/10 Excellent

Rebecca

A breakfast bar with a chalkboard sign that reads "HAPPY BREAKFAST STARTS HERE" and a variety of food and drink options.

Hampton Inn & Suites Sarasota/Bradenton-Airport, FL

Sarasota

10/10 Excellent

Mildred

A spacious lobby with a central seating area, a kitchen in the background, and a large chandelier.

Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

10/10 Excellent

Martha

A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

Home2 Suites by Hilton Nokomis Sarasota Casey Key

Nokomis

10/10 Excellent

My mom and I enjoyed our stay here and will definitely come back. We were Inn Florida for the Diana Ross concert in Sarasota but all of the hotels were pretty expensive. Nokimis is less than 30 minutes from Sarasota so we decided to stay here. I was very pleased as I am very picky when it comes to hotels. The hotel itself is pretty new (less than 2 months) and the room was spacious and very clean. The front desk reps were very nice and the complementary continental breakfast was great! ...

Tomesha

A hotel room with two beds, a desk with a telephone, a chair, a sofa, a small table with a plant, and a large window offering a city view.

Hyatt Place Sarasota Lakewood Ranch

Bradenton

10/10 Excellent

This is a great hotel in the heart of downtown Sarasota with a fantastic lobby and walking distance to just about anything. The lobby has a great vibe with a larger elegant bar and the staff is fantastic at check in. The rooms carry that modern vibe without being too much to get in the way of the experience. Great bedding and while I didn’t have any special view it was still a view of downtown so good city feel. Walking distance to Main Street with LOTS of local restaurants, stores,...

Brian