Name: The St. Regis Longboat Key Resort
Price range: CA $1,878
Rating: 9.8

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Your Longboat Key Vacation

With a reputation for its laid-back lifestyle and spectacular views, Longboat Key is an ideal getaway destination. Lock in one of our Longboat Key vacation packages and experience all that this fascinating city has to offer. IMG Academy, Coquina Beach and Cortez Beach are just a few of the attractions worth checking out during your trip to Longboat Key. Expedia will help you escape your daily routine. Tailor your vacation to Longboat Key to suit your travel style, whatever that may be.

Top Longboat Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Plaza Beach Hotel Beachfront Resort

CA $1,375

per person

May 23 - May 30

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Everything was wonderful!! Walls a little thin as we could hear neighbor's all hours of the night. Otherwise i had a wonderful experience.

Reviewed on Mar 14, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,554

per person

May 23 - May 30

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (838 reviews)

Amazing property. Clean comfortable and beautiful condo.

Reviewed on Mar 15, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

CA $2,558

per person

May 3 - May 9

found 5 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Sarasota (SRQ)

9.8/10 Exceptional! (320 reviews)

Room was beautiful and clean. Well kept and high end detail.

Reviewed on Mar 10, 2026

The Avalon Club

CA $2,435

per person

Apr 20 - Apr 27

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9.4/10 Exceptional! (515 reviews)

Our family had a wonderful 4-night stay at this well kept hotel. The apartment was spacious, very clean, had nice amenities, and the hotel is conveniently located just steps from the beach. We recommend and would be happy to stay there again.

Reviewed on Mar 13, 2026

FUSION Resort Waterfront Suites

CA $1,619

per person

Apr 20 - Apr 27

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9.2/10 Wonderful! (1,135 reviews)

Rooms were big and the views are gorgeous. We brought our boat but had issues with finding a place to unload boat and store our trailer.

Reviewed on Mar 15, 2026

Ready to book your vacation to Longboat Key?

Choose your dates

Longboat Key Hotel Deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

CA $1,878

CA $2,223 total

Apr 6 - Apr 7

includes taxes & fees

9.8/10 Exceptional! (64 reviews)

great property great service expensive but worth it in my opinion

Reviewed on Feb 20, 2026

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Fully refundableReserve now, pay when you stay

CA $418

CA $535 total

Apr 12 - Apr 13

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Great spot for a getaway.

Reviewed on Mar 13, 2026

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Fully refundableReserve now, pay when you stay

CA $753

CA $929 total

Apr 12 - Apr 13

includes taxes & fees

9/10 Wonderful! (699 reviews)

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Reviewed on Mar 9, 2026

See all 886 properties in Longboat Key

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.