A wooden pathway surrounded by dense greenery and trees.

Find hotels in Legacy Trail, FL from $63

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Oct 19 - Oct 20
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Our top choices for Legacy Trail hotels

A pool area with a waterfall feature, lounge chairs, and palm trees.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
A covered patio with a brick floor, wicker furniture, and tropical plants.
A beach with white sand, clear blue water, and a few beach umbrellas.

1. Tropical Beach Resorts

Tropical Beach Resorts
South Village
United States
Liliana
$162 nightly
$183 total
Oct 21 - Oct 22
Total with taxes and fees
Tropical Beach Resorts
A spacious indoor area with wooden tables and chairs, large windows, and hanging plants.
A modern interior with a central white table, a glass display case, and a sign indicating a market area.
A hotel corridor with wooden paneling, large windows, and a view of a pool area.
Two lounge chairs with striped cushions, a wooden bench, and a decorative metal plant structure.

2. Kompose Boutique Hotel

Kompose Boutique Hotel
Sarasota
United States
Natalia
$68 nightly
$76 total
Oct 29 - Oct 30
Total with taxes and fees
Kompose Boutique Hotel
A spacious restaurant with high ceilings, hanging wicker chandeliers, and a view of the sea through large windows.
A pool area with umbrellas, lounge chairs, and a view of the marina.
A reception area with a wooden counter, tropical plants, and a sign reading "Mi Casa Es Su Casa".
A marina at night with boats docked and a distant city skyline.

3. Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound
Bradenton
United States
Christina
$153 nightly
$173 total
Nov 1 - Nov 2
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 swimming pool with lounge chairs and palm trees, surrounded by string lights.
A bedroom with a bed, bedside tables, a desk, and a chair.
A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.

4. Siesta Key Palms Resort

Siesta Key Palms Resort
Sarasota
United States
Jonathan
$111 nightly
$125 total
Nov 18 - Nov 19
Total with taxes and fees
Siesta Key Palms Resort
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 modern restaurant with a long counter, multiple dining tables, and large windows offering a view of the sea.
A bar area with wooden furniture and hanging lights, overlooking a pool and beach area.

5. Lido Beach Resort

Lido Beach Resort
Lido Key
United States
Debra
$365 nightly
$412 total
Oct 25 - Oct 26
Total with taxes and fees
Lido Beach Resort
Beach
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.
A modern bathroom with a large mirror, a wooden cabinet, and a television mounted on the wall.
A room with a blue patterned wall, a wooden floor, a blue sofa, a wooden bench, and a bed with a white headboard.

6. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
South Village
United States
Richard
$122 nightly
$138 total
Oct 20 - Oct 21
Total with taxes and fees
Cottages at Siesta Key Inn
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.
A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.
An outdoor patio with a fire feature, seating, and a bar area.

7. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
United States
Gaeliel
$97 nightly
$109 total
Oct 27 - Oct 28
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
A hotel pool area with lounge chairs and a covered seating area.
A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.
A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.
A hotel room with two beds, a kitchenette, a TV, and a desk.

8. Carlisle Inn

Carlisle Inn
Pinecraft
United States
Rachel
$149 nightly
$168 total
Oct 20 - Oct 21
Total with taxes and fees
Carlisle Inn
A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.
A swimming pool with blue lounge chairs and palm trees.
An outdoor seating area with blue cushioned sofas and tables, a thatched roof, and a sign for Big Tiko Lounge.
A modern living room with a blue sofa, wooden coffee table, and a bookshelf.

9. Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites
Siesta Key Village
United States
Matthew
$232 nightly
$262 total
Nov 1 - Nov 2
Total with taxes and fees
Siesta Key Beach Resort and Suites
A modern hotel room with a large bed, a desk, and a view of the ocean.
A modern hotel lobby with a curved orange sofa, green walls, and a large chandelier.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear blue sky.
A hotel room with two beds, a large mirror, a TV, and a balcony with curtains.

10. Cirque St. Armands Beachside

Cirque St. Armands Beachside
Lido Key
United States
Yuliesvy
$284 nightly
$321 total
Oct 20 - Oct 21
Total with taxes and fees
Cirque St. Armands Beachside
A pathway flanked by palm trees and a building with a covered patio area.
A modern bedroom with two beds, a desk, a chair, a TV, and a balcony with a view of greenery.
A resort with a pool, sun loungers, and a wooden deck.
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
Alecssandre
$131 nightly
$148 total
Oct 25 - Oct 26
Total with taxes and fees
Casey Key Resorts - Mainland
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 hotel room with a bed, a TV mounted on the wall, a bedside table with a lamp, and a wardrobe.
A modern apartment with a living room, a dining area, a kitchen, and a TV mounted on the wall.

12. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
Sarasota
United States
Kat
$123 nightly
$139 total
Oct 20 - Oct 21
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
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.
A modern living room with a large flat-screen TV, a sofa, and a dining area with a table and chairs.
A couple walking on a beach with clear skies and ocean waves.

13. Tropical Breeze Resort

Tropical Breeze Resort
Siesta Key Village
United States
Mileidys
$127 nightly
$144 total
Nov 18 - Nov 19
Total with taxes and fees
Tropical Breeze Resort
A tropical resort with a paved walkway, outdoor seating area, and a view of the beach.
A beachfront hotel with multiple floors, palm trees, and a sandy beach.
A pool area with lounge chairs, palm trees, and a view of the beach.
A hotel room with a large bed, a ceiling fan, a view of the ocean, and a window with curtains.

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
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.

15. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
United States
Jymieka
$101 nightly
$114 total
Oct 29 - Oct 30
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A rooftop terrace with a fire feature, seating area, and a view of the city skyline.
A modern lobby with a vertical garden, seating area, and a bar.
A modern restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.
A modern hotel with multiple floors, large windows, and a prominent entrance.

16. The Westin Sarasota

The Westin Sarasota
Central Sarasota
United States
mike
$281 nightly
$318 total
Oct 29 - Oct 30
Total with taxes and fees
The Westin Sarasota
A pool area with lounge chairs and palm trees, overlooking the ocean at sunset.
A beach with a thatched-roof structure, lounge chairs, and umbrellas.
A spacious lobby with a grand chandelier, elegant seating, and a reflective floor.
A resort with a pool, palm trees, and a view of the ocean.

17. The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota
Central Sarasota
United States
Rene
$618 nightly
$698 total
Nov 18 - Nov 19
Total with taxes and fees
The Ritz-Carlton, Sarasota
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.
A sandy beach path with wooden posts and ropes, leading towards the ocean.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a marble island.
A wooden deck with chairs and a table overlooking a body of water.

18. Turtle Beach Resort

Turtle Beach Resort
Siesta Key
United Kingdom
Susan
$287 nightly
$321 total
Nov 1 - Nov 2
Total with taxes and fees
Turtle Beach Resort
A wide beach with a clear sky and distant buildings.
A palm tree-lined pathway with a bench and a flag in the background.
A hotel room with a bed, a sofa, a dining table, wicker chairs, a ceiling fan, and a potted plant.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

19. The Capri at Siesta

The Capri at Siesta
South Village
United States
Elijah
The Capri at Siesta
A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A pathway leading to a white staircase surrounded by lush greenery and palm trees.
A round table with two green placemats, a yellow napkin, and a glass vase with a pink flower.

20. Inn at the Beach

Inn at the Beach
Venice Island
United States
Florence
$175 nightly
$198 total
Nov 16 - Nov 17
Total with taxes and fees
Inn at the Beach
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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 paved road flanked by dense tropical vegetation.

Top Legacy Trail Hotel Reviews

More cheap stays in Legacy Trail

Red Roof Inn PLUS+ Miami Airport

Red Roof Inn PLUS+ Miami Airport

3401 NW Lejeune Road Miami FL
$56 nightly
$63 total
Oct 26 - Oct 27
Total with taxes and fees
Red Roof Inn PLUS+ Miami Airport
Red Carpet Inn Airport and Cruise Port Hotel Fort Lauderdale

Red Carpet Inn Airport and Cruise Port Hotel Fort Lauderdale

2460 W State Road 84 Fort Lauderdale FL
$57 nightly
$64 total
Oct 21 - Oct 22
Total with taxes and fees
Red Carpet Inn Airport and Cruise Port Hotel Fort Lauderdale
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

12525 Front Beach Rd Panama City Beach FL
$57 nightly
$65 total
Nov 19 - Nov 20
Total with taxes and fees
7/10 Good! (2,315 reviews)
Chateau Beachfront Hotel, A By The Sea Resort
Clarion Inn & Suites Miami International Airport

Clarion Inn & Suites Miami International Airport

5325 NW 36th Street Miami Springs FL
$64 nightly
$73 total
Oct 20 - Oct 21
Total with taxes and fees
Clarion Inn & Suites Miami International Airport
Ramada by Wyndham Miami Springs/Miami International Airport

Ramada by Wyndham Miami Springs/Miami International Airport

5001 NW 36th St. Miami Springs FL
$69 nightly
$78 total
Oct 27 - Oct 28
Total with taxes and fees
Ramada by Wyndham Miami Springs/Miami International Airport
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

715 1st St N Jacksonville Beach FL
$151 nightly
$171 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (4,609 reviews)
Margaritaville Jacksonville Beach

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