Name: The St. Regis Longboat Key Resort
Price range: CA $1,236
Rating: 9.8

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.

ChartHouse Clearwater Beach Marina Hotel

CA $1,072

per person

Jul 25 - Jul 31

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,005 reviews)

Overall, a good place for the vacation

Reviewed on May 15, 2026

The BC Resort on the Water

CA $1,103

per person

Jun 29 - Jul 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

7.8/10 Good! (18 reviews)

We had a great stay at this condo during our trip to Florida. Everything was very clean and well maintained, which made it easy to relax right away. Communication was excellent—clear, prompt, and the instructions were simple to follow from check-in to check-out. The accommodations were comfortable and nicely set up, with everything we needed for our stay. The location was a big highlight—perfect for easy beach access and close to plenty of activities. We would definitely stay here again.

Reviewed on Apr 24, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,882

per person

Jun 29 - Jul 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (932 reviews)

Nice location Easy check in and out Great ocean view and walkable to beach Nice pool Easy to park vehicle on property Some of the staff were super friendly. Room was lovely but beds need to be replaced. In room washer and dryer did not work properly.

Reviewed on May 17, 2026

Cedar Cove Resort and Cottages

CA $1,588

per person

Jul 27 - Aug 3

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.2/10 Wonderful! (506 reviews)

Property was great! I would definitely recommend people to stay here great place parking is a bit of an issue if you have more than one car coming in but that comes with the island pretty typical but overall great

Reviewed on May 17, 2026

Wyndham Grand Clearwater Beach

CA $1,613

per person

Jul 25 - Jul 31

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (3,219 reviews)

All good ..customer service was great

Reviewed on May 17, 2026

Ready to book your vacation to Longboat Key?

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Longboat Key Hotel Deals

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Fully refundableReserve now, pay when you stay

CA $342

CA $449 total

May 31 - Jun 1

includes taxes & fees

9/10 Wonderful! (1,007 reviews)

"A great place to stay with very convenient amenities. The pool area and beach access are very clean, accessible, and accommodating to all guests."

Reviewed on May 15, 2026

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

Fully refundableReserve now, pay when you stay

CA $1,236

CA $1,498 total

Jun 9 - Jun 10

includes taxes & fees

9.8/10 Exceptional! (73 reviews)

"Lovely new five star resort, great room designs w ocean views and great pools. Only issue was getting reservations at the steak restaurant so make sure you book before you arrive."

Reviewed on May 14, 2026

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Fully refundableReserve now, pay when you stay

CA $659

CA $822 total

May 26 - May 27

includes taxes & fees

9/10 Wonderful! (708 reviews)

"I received a pedicure while a guest there. My pedicurist was a lot of fun. I relaxed, & we laughed a lot. SHe was professional, positive, and fun. The pedicure was pretty good, but the experience was excellent."

Reviewed on Apr 30, 2026

See all 876 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.