A wooden pathway surrounded by dense greenery and trees.

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Our top choices for Legacy Trail hotels

A pool area with a waterfall feature, lounge chairs, and palm trees.
A beach with white sand, clear blue water, and a few beach umbrellas.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.

1. Tropical Beach Resorts

Tropical Beach Resorts
South Village
United States
Diana
$141 nightly
$160 total
Sep 3 - Sep 4
Total with taxes and fees
Tropical Beach Resorts
A spacious indoor area with wooden tables and chairs, large windows, and hanging plants.
Two lounge chairs with striped cushions, a wooden bench, and a decorative metal plant structure.
A hotel corridor with wooden paneling, large windows, and a view of a pool area.
A swimming pool with lounge chairs, palm trees, and a building with large windows.

2. Kompose Boutique Hotel

Kompose Boutique Hotel
Sarasota
United States
Barry
$62 nightly
$71 total
Sep 7 - Sep 8
Total with taxes and fees
Kompose Boutique Hotel
A pool area with lounge chairs and umbrellas, a palm tree, and a view of the ocean.
A coastal hotel with multiple buildings, a beach with sun loungers, and clear blue waters.
A bar area with wooden furniture and hanging lights, overlooking a pool and beach area.
A modern restaurant with a long counter, multiple dining tables, and large windows offering a view of the sea.

3. Lido Beach Resort

Lido Beach Resort
Lido Key
United States
Faris
$357 nightly
$403 total
Sep 20 - Sep 21
Total with taxes and fees
Lido Beach Resort
A spacious restaurant with high ceilings, hanging wicker chandeliers, and a view of the sea through large windows.
A reception area with a wooden counter, tropical plants, and a sign reading "Mi Casa Es Su Casa".
A pool area with umbrellas, lounge chairs, and a view of the marina.
A poolside area with multiple blue umbrellas, lounge chairs, and palm trees.

4. Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound
Bradenton
United States
Michael
$168 nightly
$190 total
Sep 11 - Sep 12
Total with taxes and fees
Compass Hotel by Margaritaville Anna Maria Sound
A covered outdoor area with a pool, lounge chairs, and a wooden deck.
A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.
A bedroom with a bed, bedside tables, a desk, and a chair.
A swimming pool with lounge chairs and palm trees, surrounded by string lights.

5. Siesta Key Palms Resort

Siesta Key Palms Resort
Sarasota
United States
elimel
$106 nightly
$120 total
Sep 9 - Sep 10
Total with taxes and fees
Siesta Key Palms Resort
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.
An outdoor patio with a fire feature, seating, and a bar area.
A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.

6. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
United States
Tina
$93 nightly
$106 total
Sep 7 - Sep 8
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
A modern bathroom with a large mirror, a wooden cabinet, and a television mounted on the wall.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.
A bedroom with a bed, a TV, a wooden dresser, and a bathroom visible through an open door.

7. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
South Village
United States
Maria
$153 nightly
$173 total
Sep 22 - Sep 23
Total with taxes and fees
Cottages at Siesta Key Inn
An outdoor patio with a grill, white chairs, and a red umbrella.
A spacious room with wicker furniture, a television, and a window with a view of parked cars.
A modern kitchen with a stainless steel refrigerator, a microwave, and a sink with a faucet.
A hotel room with a bed, a TV mounted on the wall, a bedside table with a lamp, and a wardrobe.

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
Sarasota
United States
Kat
$116 nightly
$131 total
Sep 7 - Sep 8
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.
A modern living room with a blue sofa, wooden coffee table, and a bookshelf.
A bedroom with a bed, two bedside tables, a ceiling fan, and a window with blinds.
An outdoor seating area with blue cushioned sofas and tables, a thatched roof, and a sign for Big Tiko Lounge.

9. Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites
Siesta Key Village
United States
Mark
$195 nightly
$220 total
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key Beach Resort and Suites
A hotel pool area with lounge chairs and a covered seating area.
A hotel room with two beds, a kitchenette, a TV, and a desk.
A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.
A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.

10. Carlisle Inn

Carlisle Inn
Pinecraft
United States
William
$138 nightly
$156 total
Sep 17 - Sep 18
Total with taxes and fees
Carlisle Inn
A pathway flanked by palm trees and a building with a covered patio area.
A resort with a pool, sun loungers, and a wooden deck.
A modern bedroom with two beds, a desk, a chair, a TV, and a balcony with a view of greenery.
A modern reception area with a wooden reception desk, a flat-screen TV, and a sign for Casey Key Resorts Mainland.

11. Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
Osprey
United States
Staci
$104 nightly
$118 total
Sep 3 - Sep 4
Total with taxes and fees
Casey Key Resorts - Mainland
A stone pathway leading through a tropical garden with palm trees and a signboard.
An aerial view of a uniquely shaped swimming pool surrounded by palm trees and lounge chairs.
An outdoor patio with wicker furniture and a thatched roof.
A couple walking on a beach with clear skies and ocean waves.

12. Tropical Breeze Resort

Tropical Breeze Resort
Siesta Key Village
United States
James
$156 nightly
$177 total
Sep 7 - Sep 8
Total with taxes and fees
Tropical Breeze Resort
An outdoor seating area with wicker furniture, a glass-top table, and a view of a lake and fountain.
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.
A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.
A hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

13. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
United States
Carol
$90 nightly
$101 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A tropical resort with a paved walkway, outdoor seating area, and a view of the beach.
A living room with a large window overlooking the sea, a flat-screen TV mounted on the wall, and a yellow armchair.
A hotel room with a large bed, a ceiling fan, a view of the ocean, and a window with curtains.
A beachfront hotel with multiple floors, palm trees, and a sandy beach.

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

The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
United States
Janell
The Residences at Siesta Key Beach by Hyatt Vacation Club
A spacious indoor area with a high ceiling, large windows, and a central bar area.
A modern hotel room with a large window, a flat-screen TV, a sofa, a small table, and a desk with a lamp.
A spacious indoor area with a bar, seating, and large windows offering a view of the sunset.
A modern indoor pool with clear views of the city skyline, large windows, and a spacious lounge area.

15. Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL
Central Sarasota
United States
Andrea
$163 nightly
$185 total
Sep 9 - Sep 10
Total with taxes and fees
Embassy Suites by Hilton Sarasota, FL
A modern hotel room with a large bed, a desk, and a view of the ocean.
A restaurant with round tables and chairs, large windows, and a view of palm trees.
A hotel room with two beds, a large mirror, a TV, and a balcony with curtains.
A modern hotel lobby with a curved orange sofa, green walls, and a large chandelier.

16. Cirque St. Armands Beachside

Cirque St. Armands Beachside
Lido Key
United States
Genea
$264 nightly
$298 total
Sep 3 - Sep 4
Total with taxes and fees
Cirque St. Armands Beachside
A beach with people sunbathing and swimming.
A modern kitchen with white cabinets, a dining area with a white table and chairs, a blue sofa with white cushions, and a ceiling fan.
A modern kitchen with white cabinetry, a white dining table, and a chandelier.
A tropical resort with a thatched-roof hut, a wooden bench, and a white fence.

17. Siesta Key Beachside Villas

Siesta Key Beachside Villas
Siesta Key Village
United States
Jeannie
$197 nightly
$223 total
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key Beachside Villas
A rooftop terrace with a fire feature, seating area, and a view of the city skyline.
A modern restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.
A modern lobby with a vertical garden, seating area, and a bar.
A modern lobby with a vertical garden, comfortable seating, and a geometric light fixture.

18. The Westin Sarasota

The Westin Sarasota
Central Sarasota
United States
Racheal
$166 nightly
$187 total
Sep 7 - Sep 8
Total with taxes and fees
The Westin Sarasota
A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.
A pathway leading to a white staircase surrounded by lush greenery and palm trees.
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A hotel with a palm tree entrance, a neon sign, and a tiled roof.

19. Inn at the Beach

Inn at the Beach
Venice Island
United States
Barney
$126 nightly
$143 total
Sep 7 - Sep 8
Total with taxes and fees
Inn at the Beach
A spacious restaurant with wooden ceilings and large windows offering a view of the ocean. Tables are set with white chairs and dining ware.
A beachfront hotel with multiple buildings, a swimming pool, and a beach with umbrellas.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A spacious lobby with a modern sofa set, a round coffee table, and a small seating area with stools.

20. Zota Beach Resort

Zota Beach Resort
Longboat Key
United States
Jason
$249 nightly
$281 total
Sep 3 - Sep 4
Total with taxes and fees
Zota Beach Resort
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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
A wooden pathway surrounded by dense greenery and trees.

Top Legacy Trail Hotel Reviews

More cheap stays in Legacy Trail

Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

12525 Front Beach Rd Panama City Beach FL
$52 nightly
$59 total
Sep 3 - Sep 4
Total with taxes and fees
7/10 Good! (2,089 reviews)
Chateau Beachfront Hotel, A By The Sea Resort
Baymont by Wyndham Orlando North Millenia

Baymont by Wyndham Orlando North Millenia

2500 33Rd Street Orlando FL
$55 nightly
$61 total
Sep 17 - Sep 18
Total with taxes and fees
7/10 Good! (2,232 reviews)
Baymont by Wyndham Orlando North Millenia
Ramada by Wyndham Miami Springs/Miami International Airport

Ramada by Wyndham Miami Springs/Miami International Airport

5001 NW 36th St. Miami Springs FL
$56 nightly
$64 total
Sep 8 - Sep 9
Total with taxes and fees
Ramada by Wyndham Miami Springs/Miami International Airport
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL
$66 nightly
$73 total
Sep 13 - Sep 14
Total with taxes and fees
6.8/10 (1,159 reviews)
Baymont by Wyndham Fort Myers Central
Best Western Aku Tiki Inn

Best Western Aku Tiki Inn

2225 S Atlantic Ave Daytona Beach Shores FL
$85 nightly
$95 total
Sep 9 - Sep 10
Total with taxes and fees
Best Western Aku Tiki Inn
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

715 1st St N Jacksonville Beach FL
$169 nightly
$192 total
Sep 3 - Sep 4
Total with taxes and fees
9/10 Wonderful! (4,421 reviews)
Margaritaville Jacksonville Beach

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