A wooden pathway surrounded by dense greenery and trees.

Find hotels in Legacy Trail, FL from $63

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Filter by

Star rating

Guest rating

Our top choices for Legacy Trail hotels

A pool area with a waterfall feature, lounge chairs, and palm trees.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.
A beach with white sand, clear blue water, and a few beach umbrellas.
A covered patio with a brick floor, wicker furniture, and tropical plants.

1. Tropical Beach Resorts

Tropical Beach Resorts
South Village
United States
kurt
$150 nightly
$170 total
Oct 12 - Oct 13
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 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.

2. Kompose Boutique Hotel

Kompose Boutique Hotel
Sarasota
United States
Natalia
$56 nightly
$63 total
Oct 19 - Oct 20
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 poolside area with multiple blue umbrellas, lounge chairs, and palm trees.
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
$174 nightly
$197 total
Oct 20 - Oct 21
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 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.
A bar area with a wooden ceiling, bar stools, and a neon sign.

4. Siesta Key Palms Resort

Siesta Key Palms Resort
Sarasota
United States
Jonathan
$111 nightly
$125 total
Oct 18 - Oct 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 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.
A coastal hotel with multiple buildings, a beach with sun loungers, and clear blue waters.

5. Lido Beach Resort

Lido Beach Resort
Lido Key
United States
Faris
$357 nightly
$403 total
Oct 12 - Oct 13
Total with taxes and fees
Lido Beach Resort
Beach
A modern bathroom with a large mirror, a wooden cabinet, and a television mounted on the wall.
A bedroom with a bed, a TV, a wooden dresser, and a bathroom visible through an open door.
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
Cassie
$140 nightly
$159 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 hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.
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.

7. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
United States
Gaeliel
$106 nightly
$120 total
Oct 11 - Oct 12
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 lobby with a reception desk, seating area, and decorative wall art.
A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.

8. Carlisle Inn

Carlisle Inn
Pinecraft
United States
Darrel
$148 nightly
$167 total
Oct 11 - Oct 12
Total with taxes and fees
Carlisle Inn
A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.
A bedroom with a bed, two bedside tables, a ceiling fan, and a window with blinds.
A modern living room with a blue sofa, wooden coffee table, and a bookshelf.
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
Vanessa
$266 nightly
$301 total
Oct 11 - Oct 12
Total with taxes and fees
Siesta Key Beach Resort and Suites
A closet with a poster of Barnum & Bailey Greatest Show on Earth, a bench, and hanging clothes.
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.

10. Cirque St. Armands Beachside

Cirque St. Armands Beachside
Lido Key
United States
Yuliesvy
$294 nightly
$332 total
Oct 18 - Oct 19
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 modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views 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
Alecssandre
$99 nightly
$111 total
Oct 9 - Oct 10
Total with taxes and fees
Casey Key Resorts - Mainland
An outdoor patio with a grill, white chairs, and a red umbrella.
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.
A spacious room with wicker furniture, a television, and a window with a view of parked cars.

12. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
Sarasota
United States
Kat
$127 nightly
$144 total
Oct 12 - Oct 13
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.
A modern living room with a large flat-screen TV, a sofa, and a dining area with a table and chairs.
An outdoor patio with wicker furniture and a thatched roof.
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
$199 nightly
$225 total
Oct 25 - Oct 26
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 pool area with lounge chairs, palm trees, and a view of the beach.
A beachfront hotel with multiple floors, palm trees, and a sandy 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 hotel room with two beds, a nightstand, and a desk.
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
$95 nightly
$108 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 lobby with a vertical garden, comfortable seating, and a geometric light fixture.
A modern restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

16. The Westin Sarasota

The Westin Sarasota
Central Sarasota
United States
THANG
$281 nightly
$318 total
Oct 25 - Oct 26
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 resort with a pool, palm trees, and a view of the ocean.
A spacious lobby with a grand chandelier, elegant seating, and a reflective floor.

17. The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota
Central Sarasota
United States
Glenn
$618 nightly
$698 total
Nov 8 - Nov 9
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 wooden deck with chairs and a table overlooking a body of water.
A narrow stone pathway flanked by lush green plants and a wooden pergola structure.

18. Turtle Beach Resort

Turtle Beach Resort
Siesta Key
United Kingdom
Susan
$294 nightly
$328 total
Nov 1 - Nov 2
Total with taxes and fees
Turtle Beach Resort
A wide beach with a clear sky and distant buildings.
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.
A palm tree-lined pathway with a bench and a flag in the background.

19. The Capri at Siesta

The Capri at Siesta
South Village
United States
Yalennis Almaguer
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 hotel with a palm tree entrance, a neon sign, and a tiled roof.

20. Inn at the Beach

Inn at the Beach
Venice Island
United States
Christina
$178 nightly
$201 total
Oct 20 - Oct 21
Total with taxes and fees
Inn at the Beach
View all properties
Save an average of 15% on thousands of hotels when you're signed in

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 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
$56 nightly
$63 total
Oct 13 - Oct 14
Total with taxes and fees
Red Carpet Inn Airport and Cruise Port Hotel Fort Lauderdale
Red Roof Inn PLUS+ Miami Airport

Red Roof Inn PLUS+ Miami Airport

3401 NW Lejeune Road Miami FL
$59 nightly
$66 total
Oct 12 - Oct 13
Total with taxes and fees
7/10 Good! (2,910 reviews)
Red Roof Inn PLUS+ Miami Airport
Ramada by Wyndham Miami Springs/Miami International Airport

Ramada by Wyndham Miami Springs/Miami International Airport

5001 NW 36th St. Miami Springs FL
$59 nightly
$67 total
Oct 12 - Oct 13
Total with taxes and fees
Ramada by Wyndham Miami Springs/Miami International Airport
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

12525 Front Beach Rd Panama City Beach FL
$60 nightly
$67 total
Oct 18 - Oct 19
Total with taxes and fees
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
$63 nightly
$71 total
Oct 12 - Oct 13
Total with taxes and fees
Clarion Inn & Suites Miami International Airport
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

715 1st St N Jacksonville Beach FL
$184 nightly
$209 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (4,575 reviews)
Margaritaville Jacksonville Beach

Explore a world of travel with Expedia