Longboat Key Vacations 2026 from CA $888

Longboat Key flight + hotel packages

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

Family Home Tampa

Forest Hills

CA $888

per person

Mar 3 - Mar 9

found 17 hours ago

Roundtrip flight included

Toronto (YYZ) to Sarasota (SRQ)

Stay at this guesthouse in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Busch Gardens Tampa Bay and Raymond James Stadium are located nearby.

Saddlebrook Resort

Wesley Chapel South

CA $958

per person

Feb 14 - Feb 20

found 1 day ago

Roundtrip 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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

CA $2,071

per person

Feb 27 - Mar 3

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.

voco Sarasota by IHG

Central Sarasota

CA $2,155

per person

Mar 4 - Mar 11

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Hotel Tampa Riverwalk

Downtown Tampa

CA $1,562

per person

Feb 6 - Feb 11

found 13 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Sarasota (SRQ)

Book a stay at this business-friendly hotel in Tampa. Enjoy 2 bars/lounges, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa 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 $1,252 total

Dec 14 - Dec 15

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 6 - Jan 7, 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 $619

CA $761 total

Dec 14 - Dec 15

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

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key FL

CA $274

CA $536 total

Dec 13 - Dec 14

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

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

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Longboat Key FL

Get rates

Book a stay at this beach condo in Longboat Key. Enjoy free WiFi, private pools, and a beach locale. 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 $888. 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.