Longboat Key Vacations 2025 from CA $550

Longboat Key flight + hotel packages

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

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Wesley Chapel South

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

Book a stay at this golf 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

May 18 - May 25

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

Stay at this 4-star beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. 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 Avalon Club

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Legacy Vacation Resorts - Indian Shores

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

Stay at this 3-star beach aparthotel in Indian Shores. Enjoy free WiFi, free parking, 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 St. Petersburg - Clearwater Beaches are located nearby.

FUSION Resort Waterfront Suites

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

Stay at this 3.5-star 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 Upham Beach are located nearby.

Top Longboat Key hotels deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive, Longboat Key, FL

CA $1,558

CA $1,849 total

includes taxes & fees

22 Apr - 23 Apr

Stay at this 5-star luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions St. Armands Circle and Lido Beach 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 $471

CA $597 total

includes taxes & fees

27 Apr - 28 Apr

Stay at this 4-star 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 Cortez Beach 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 $943

CA $1,130 total

includes taxes & fees

1 Apr - 2 Apr

Stay at this 4-star beach resort in Longboat Key. Enjoy free WiFi, free valet parking, and a full-service spa. Popular attractions St. Armands Circle and Lido Beach are located nearby.

On private beach

Pool

Sea Club I Beach Resort

4141 Gulf of Mexico Drive, Longboat Key, FL

Get rates

Stay at this 3-star 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 John and Mable Ringling Museum of Art and Coquina Beach are located nearby.

Pool

Kitchen

The Beach on Longboat Key #104 Resort by RVA

CA $223

CA $478 total

includes taxes & fees

30 Mar - 31 Mar

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

Pool

Kitchen

THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW

CA $408

CA $709 total

includes taxes & fees

5 Apr - 6 Apr

Stay at this apartment in Longboat Key. Enjoy free WiFi, a picnic area, and patios. Popular attractions St. Armands Circle and Lido Beach are located nearby.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Longboat Key

View all properties

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.

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.

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.

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 $550. 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.