Longboat Key Vacations 2026 from CA $693

Longboat Key flight + hotel packages

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

Saddlebrook Resort

Wesley Chapel South

CA $693

per person

Feb 19 - Feb 22

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.

FUSION Resort Waterfront Suites

CA $1,260

per person

Feb 15 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

CA $3,199

per person

Feb 28 - Mar 7

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Sarasota (SRQ)

Book a stay at this beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Plaza Beach Hotel Beachfront Resort

CA $2,666

per person

Mar 7 - Mar 14

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

Bayview Plaza Waterfront Resort

Belle Vista

CA $1,325

per person

Mar 7 - Mar 14

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

Top Longboat Key hotels deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

CA $1,018

CA $1,251 total

Dec 17 - Dec 18

includes taxes & fees

Book a stay at this luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions Lido Beach and St. Armands Circle are located nearby.

On private beach

Pool

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Free cancellation

Reserve now, pay when you stay

CA $315

CA $419 total

Jan 5 - Jan 6, 2026

includes taxes & fees

Book a stay at this beach resort in Longboat Key. Enjoy free WiFi, a private beach, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Coquina Beach and Longboat Key Beaches are located nearby.

On private beach

Pool

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Free cancellation

Reserve now, pay when you stay

CA $618

CA $761 total

Dec 15 - Dec 16

includes taxes & fees

Book a stay at this beach resort in Longboat Key. Enjoy free WiFi, free valet parking, and a full-service spa. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

On private beach

Pool

Sea Club I Beach Resort

4141 Gulf of Mexico Drive Longboat Key FL

Get rates

Book a stay at this beach apartment in Longboat Key. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Longboat Key Beaches are located nearby.

Pool

Kitchen

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key FL

CA $274

CA $539 total

Dec 19 - Dec 20

includes taxes & fees

Book a stay at this beach apartment in Longboat Key. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Lido Beach and St. Armands Circle are located nearby.

Pool

Kitchen

Longboat Bay Club

3200 Gulf of Mexico Dr Longboat Key FL

Get rates

Stay at this condo in Longboat Key. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Lido Beach and St. Armands Circle are located nearby.

Pool

Kitchen

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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.

Popular places to visit

Jewfish Key

Commune with nature and explore the great outdoors at Jewfish Key during your travels in Longboat Key. Wander the beautiful beaches in this relaxing area.

Islandside Golf Course at Longboat Key Club

Enjoy a round of golf in Longboat Key at Islandside Golf Course at Longboat Key Club. Wander the beautiful beaches or discover the area's beautiful sunsets.

Harborside Golf Course at Longboat Key Club

Enjoy a round of golf in Longboat Key at Harborside Golf Course at Longboat Key Club. Wander the beautiful beaches or discover the area's beautiful sunsets.

Frequently asked questions

How much are vacation packages to Longboat Key?

Enjoy an unforgettable experience in Longboat Key with a vacation package starting at just CA $693. Organizing your hotels, flights and tours with Travelocity is so simple. And even better, our great deals will leave you with more savings in your pocket for fun, fun, fun!

Where can I get the best vacation package deals for Longboat Key?

Travelocity will be able to help you lock in an unbeatable Longboat Key package deal. With as many as 400 air carriers and 1,000,000 properties across the globe, we know you'll find the perfect mix.

Why should I book my Longboat Key vacation package via Travelocity?

We've got destinations to suit every type of globetrotter, top-notch service and 24/7 support. And the icing on the cake is we'll match any lower price you discover with our Price Match Guarantee.

Can I save money on my Longboat Key car rental if I book it with hotels and flights?

You certainly can with our Longboat Key vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Combine any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With your own set of wheels, all the main sights around Longboat Key are within your reach.