4 Stars Hotels in Legacy Trail, Florida from CA $116

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Legacy Trail 4-star hotels

A rooftop swimming pool with a clear blue water surface, surrounded by lounge chairs and a row of palm trees.

1. Kompose Boutique Hotel

Kompose Boutique Hotel
3.0 star property
Sarasota
9.2 out of 10, Wonderful, (6,246 reviews)
"Friendly staf., good breakfast ."
United States
Antonio
The price is CA $50
CA $87 total
includes taxes & fees
Dec 1 - Dec 2
Kompose Boutique Hotel
Beach

2. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
3.0 star property
South Village
8.8 out of 10, Excellent, (296 reviews)
"Basic no frills place to stay."
United States
Richard
The price is CA $152
CA $172 total
includes taxes & fees
Dec 11 - Dec 12
Cottages at Siesta Key Inn
A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.

3. Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites
2.5 star property
Siesta Key Village
9.2 out of 10, Wonderful, (1,200 reviews)
"Awesome place. Beach was steps away and the hotel had wagons , beach chairs and coolers to use. I would definitely stay here again."
United States
Brandon
The price is CA $180
CA $282 total
includes taxes & fees
Nov 16 - Nov 17
Siesta Key Beach Resort and Suites
A beach with white sand, clear blue sky, and colorful beach chairs.

4. Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort
3.0 star property
St. Pete Beach
9.0 out of 10, Wonderful, (1,006 reviews)
"This is our third year in spending our vacation at this beautiful, quaint little resort. The location is fantastic, the customer service is unmatched, and all the amenities are top-notch. We will definitely be back again!"
United States
Elizabeth
The price is CA $132
CA $219 total
includes taxes & fees
Nov 18 - Nov 19
Plaza Beach Hotel Beachfront Resort
A hotel room with a bed, a television, a desk, and a chair.

5. The Beachcomber

The Beachcomber
2.5 star property
St. Pete Beach
8.2 out of 10, Very good, (1,021 reviews)
"Restaurant behind the hotel was great"
United States
Gregory
The price is CA $142
CA $222 total
includes taxes & fees
Nov 15 - Nov 16
The Beachcomber
A narrow pathway flanked by palm trees and tropical plants, leading to a gated area with a pool visible in the distance.

6. The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn
2.0 star property
Bradenton Beach
8.6 out of 10, Excellent, (251 reviews)
"Great location!! Close to the beach and the bay!!! Staff was so friendly and helpful! Can't wait to come back!"
United States
Richard
The price is CA $188
CA $238 total
includes taxes & fees
Nov 16 - Nov 17
The Retreat at Anna Maria Island Inn
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the water.

7. Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound
4.0 star property
Bradenton
9.4 out of 10, Exceptional, (2,641 reviews)
"Very nice hotel, great breakfast and great happy hour."
United States
Grisel
The price is CA $205
CA $272 total
includes taxes & fees
Nov 22 - Nov 23
Compass Hotel by Margaritaville Anna Maria Sound
A beach scene with two striped beach chairs and a striped umbrella labeled "SIRATA" on a sandy beach at sunset.

8. Sirata St. Pete Beach Resort, Tapestry Collection by Hilton

Sirata St. Pete Beach Resort, Tapestry Collection by Hilton
3.5 star property
St. Pete Beach
8.4 out of 10, Very good, (761 reviews)
"Nice hotel, helpful and friendly staff, beautiful beach."
United States
Carol
The price is CA $240
CA $328 total
includes taxes & fees
Nov 24 - Nov 25
Sirata St. Pete Beach Resort, Tapestry Collection by Hilton
A beachside hotel with a view of the ocean, outdoor seating, and a mural on the building.

9. RumFish Beach at TradeWinds

RumFish Beach at TradeWinds
4.0 star property
St. Pete Beach
8.2 out of 10, Very good, (2,397 reviews)
"Staff and resort were amazing! We loved our stay there was a lot to do with beautiful views. All the staff were very friendly and the drinks were delicious!"
United States
Nathan
The price is CA $214
CA $330 total
includes taxes & fees
Dec 13 - Dec 14
RumFish Beach at TradeWinds
A beach view with a hotel building, palm trees, and beach umbrellas.

10. St Pete Shores Hotel

St Pete Shores Hotel
3.0 star property
St. Pete Beach
7.4 out of 10, Good, (1,718 reviews)
"Staff was extremely friendly and helpful"
United States
Pamela
The price is CA $235
CA $330 total
includes taxes & fees
Dec 13 - Dec 14
St Pete Shores Hotel
A resort with a large central pool, multiple smaller pools, and a view of the ocean.

11. Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
4.0 star property
Punta Gorda
9.2 out of 10, Wonderful, (3,550 reviews)
"Great place to stay and relax no need to go anywhere out of the resort."
United States
Aaron
The price is CA $233
CA $332 total
includes taxes & fees
Nov 22 - Nov 23
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
A large resort with multiple buildings, a pool area, and a beach with sun loungers.

12. The Don CeSar

The Don CeSar
4.0 star property
St. Pete Beach
9.0 out of 10, Wonderful, (1,370 reviews)
"What a beautiful property and staff went above and beyond to make sure that our stay was wonderful."
United States
Kim
The price is CA $408
CA $526 total
includes taxes & fees
Dec 13 - Dec 14
The Don CeSar
A modern hotel room with a large bed, a desk, and a view of the ocean.

13. Cirque St. Armands Beachside

Cirque St. Armands Beachside
4.0 star property
Lido Key
9.0 out of 10, Wonderful, (1,000 reviews)
"Great stay"
United States
Christopher
The price is CA $353
CA $455 total
includes taxes & fees
Nov 15 - Nov 16
Cirque St. Armands Beachside
A modern hotel with a curved facade, multiple balconies, and a mix of glass and wood paneling.

14. GALAXY HOTEL

GALAXY HOTEL
2.0 star property
Downtown St. Petersburg
8.6 out of 10, Excellent, (1,164 reviews)
"Great location near shops and a short walk to the pier."
United States
Maria
The price is CA $196
CA $222 total
includes taxes & fees
Dec 2 - Dec 3
GALAXY HOTEL
A covered outdoor area with a pool, lounge chairs, and a wooden deck.

15. Siesta Key Palms Resort

Siesta Key Palms Resort
3.5 star property
Sarasota
9.2 out of 10, Wonderful, (1,002 reviews)
"Loved this resort, friendly staff, large rooms, close to beach and to Sarasota, nice pool, fully equipped kitchen. Would definitely recommend"
Canada
CATHERINE
The price is CA $77
CA $159 total
includes taxes & fees
Dec 3 - Dec 4
Siesta Key Palms Resort
A bar with wooden decor, shelves of bottles, and a hanging light fixture.

16. Golden Host Resort - Sarasota

Golden Host Resort - Sarasota
3.0 star property
North Trail
8.6 out of 10, Excellent, (2,685 reviews)
"Great price, very clean, beds were so comfy, and pool was very refreshing, will definitely be back and highly recommend"
United States
britnee
The price is CA $102
CA $115 total
includes taxes & fees
Dec 13 - Dec 14
Golden Host Resort - Sarasota
A resort with multiple swimming pools, palm trees, and a beach view.

17. The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort
5.0 star property
Longboat Key
9.8 out of 10, Exceptional, (110 reviews)
"This is an outstanding property with an incredible staff! One of our favorite locations!"
United States
Austin
The price is CA $1,124
CA $1,375 total
includes taxes & fees
Nov 17 - Nov 18
The St. Regis Longboat Key Resort
A beach with clear turquoise water and white sand.

18. Anna Maria Beach Resort

Anna Maria Beach Resort
3.5 star property
Holmes Beach
9.4 out of 10, Exceptional, (436 reviews)
"Quiet, relaxing place with great beach access"
United States
Nathan
The price is CA $441
CA $558 total
includes taxes & fees
Dec 13 - Dec 14
Anna Maria Beach Resort
A beach path leading to thatched-roof huts with a clear blue sky.

19. Silver Surf Gulf Beach Resort

Silver Surf Gulf Beach Resort
3.0 star property
Bradenton Beach
9.6 out of 10, Exceptional, (1,002 reviews)
"Amazing place and the hotel was excellent"
United States
Roberto
The price is CA $461
CA $562 total
includes taxes & fees
Dec 7 - Dec 8
Silver Surf Gulf Beach Resort
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

20. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
3.0 star property
Sarasota
8.2 out of 10, Very good, (2,526 reviews)
"Will stay there again."
United States
kathryn
The price is CA $128
CA $145 total
includes taxes & fees
Nov 18 - Nov 19
Spark by Hilton Sarasota Siesta Key Gateway

Top Legacy Trail Hotel Reviews

A rooftop bar with outdoor seating, a pool, and a view of the sea.
Art Ovation Hotel, Autograph Collection

Art Ovation Hotel, Autograph Collection

Art Ovation Hotel, Autograph Collection
Central Sarasota

10/10 Excellent

Nicely located, beautiful property
Canada
Yassir
Reviewed October 29, 2026
Art Ovation Hotel, Autograph Collection

Find out more about Legacy Trail

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Legacy Trail are calling your name. Known for providing first-rate service in amazing locations, each of the Legacy Trail 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Legacy Trail. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Legacy Trail, Florida, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Legacy Trail hotels with 4 Stars provide everything you need to unwind in style.

Explore a world of travel with Expedia