Longboat Key Vacations 2025/2026 from CA $763

Longboat Key flight + hotel packages

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

EVEN Hotel Sarasota-Lakewood Ranch by IHG

CA $763

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Sarasota (SRQ)

Stay at this 3.5-star hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mall at University Town Center and Nathan Benderson Park are located nearby.

voco Sarasota by IHG

Central Sarasota

CA $907

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 3.5-star 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.

FUSION Resort Waterfront Suites

CA $1,007

per person

Dec 1 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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 St. Petersburg - Clearwater Beaches are located nearby.

The Residences at Siesta Key Beach by Hyatt Vacation Club

CA $2,282

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Sarasota (SRQ)

Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free valet parking, and a beach locale. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

The Westin Sarasota

Central Sarasota

CA $1,187

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Top Longboat Key hotels deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive, Longboat Key, FL

Free cancellation

Reserve now, pay when you stay

CA $968

CA $1,180 total

Sep 15 - Sep 16

includes taxes & fees

Stay at this 5-star 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 $353

CA $461 total

Sep 15 - Sep 16

includes taxes & fees

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 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 $555

CA $690 total

Sep 23 - Sep 24

includes taxes & fees

Stay at this 4-star 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.

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 Coquina Beach and Longboat Key Beaches are located nearby.

Pool

Kitchen

THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

CA $276

CA $532 total

Sep 21 - Sep 22

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 3.5-star 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.

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 $763. 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.