Longboat Key Vacation Packages

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
per person
May 3 - May 8
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.4/10 Very Good! (46 reviews)
The lady in attendance was very helpful. I would stay here again when in the Tampa area.

Reviewed on Mar. 25, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun. 12 - Jun. 16
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (393 reviews)
I will definitely try to stay here while in the area. Perfect location and the property is amazing

Reviewed on Mar. 21, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
May 8 - May 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
This was a last minute find for and day stay for our family vacation, everyone was so friendly!

Reviewed on Jan. 19, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun. 2 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,050 reviews)
Elevator wait time and small area around the pool were the only negatives.. very clean and nice staff. I liked the water fill up by the ice machines. Great location and access to beach!

Reviewed on Mar. 28, 2025

Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jun. 20 - Jun. 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.2/10 Wonderful! (880 reviews)
Property very clean, employees are very professional, plenty of space in my room. You can hang by pool or just chill out on back deck. Firepit at nite was nice also. One thing they need to add is a shower bar(something to hold on while showering)…other then that i would book at legacy again.

Reviewed on Mar. 9, 2025

Ready to book your vacation to Longboat Key?

 

Choose your dates

Longboat Key Hotel Deals

The St. Regis Longboat Key Resort
The St. Regis Longboat Key Resort
5 out of 5
1601 Gulf Of Mexico Drive, Longboat Key, FL
The price is CA $1,559 per night from Apr. 22 to Apr. 23
CA $1,559
CA $1,850 total
includes taxes & fees
Apr 22 - Apr 23
9.8/10 Exceptional! (16 reviews)
"Need a better system for assigning chairs around adult pool...also beach lounger experience needs to be upgraded to be more luxurious probably sun beds with shade...also first day adult pool too warm waterfall was offsecond day waterfall on but was ice cold soadult pool was a bit cool must do better ..."

Reviewed on Mar. 23, 2025

The St. Regis Longboat Key Resort
Zota Beach Resort
Zota Beach Resort
4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $471 per night from Apr. 27 to Apr. 28
CA $471
CA $597 total
includes taxes & fees
Apr 27 - Apr 28
8.8/10 Excellent! (1,003 reviews)
"We stayed an extra day in Sarasota, and decided to stay here. So glad we did. The beach and pool were amazing. The staff is great, and the room was perfect as well. My only regret was not staying here from the very beginning"

Reviewed on Mar. 27, 2025

Zota Beach Resort
The Resort at Longboat Key Club
The Resort at Longboat Key Club
4 out of 5
220 Sands Point Road, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $771 per night from Apr. 28 to Apr. 29
CA $771
CA $936 total
includes taxes & fees
Apr 28 - Apr 29
8.8/10 Excellent! (639 reviews)
"Absolutely beautiful clean rooms and great service staff. Dean is the man to talk to. He went above and beyond to make sure we were taken care of."

Reviewed on Mar. 27, 2025

The Resort at Longboat Key Club
See all 869 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Longboat Key vacation package cost?
Offering excellent value package deals from CA $748 on Expedia, you’ll be surprised at how little a vacation to Longboat Key costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Longboat Key?
January, August and December are the best times to search for cheap Longboat Key vacation packages. Choosing to travel in less busy periods means you’ll typically find better prices on hotels and flights.
How many days is enough for Longboat Key?
With a well-planned itinerary, you can easily hit the top Longboat Key attractions in a few days. But if you’d like to discover hidden gems or take day trips, consider booking your Longboat Key vacation for longer.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has everything you need for a fantastic trip — coastal beaches, views and watersports are just the start. Whether you’d like to check out attractions such as Jewfish Key and Cannons Marina, or venture off the beaten track, there’s plenty to experience on your Longboat Key vacation.
How to find the best Longboat Key package deals?
Use Expedia’s handy filters to help you find some tempting Longboat Key package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Longboat Key package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it’s usually best to book your vacation package well in advance.
Is it cheaper to book a Longboat Key vacation as a package?
You can enjoy significant savings on your next Longboat Key retreat by booking a personalized vacation package. Click on the “Package” heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Longboat Key?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Longboat Key trip.
How to plan a trip to Longboat Key?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favorite season and the available activities will also help you decide when to visit Longboat Key.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Longboat Key.
  3. Decide how many days away: Start by listing all the activities and attractions you want to get to in Longboat Key. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Longboat Key vacation package.

What to do in Longboat Key

Fly Above The Sea on a Flite Scooter

Fly Above Ocean Adventure in Sarasota!

CA $359
per adult
Fly Above Ocean Adventure in Sarasota!
Fly Above Water, eFoil Adventure in Sarasota

Fly Above Water, eFoil Adventure in Sarasota

CA $359
per adult
Fly Above Water, eFoil Adventure in Sarasota
Girls on the bow watching sunset at longboat pass

Sunset Boat Tour Around Anna Maria Island

CA $573
per traveller
Sunset Boat Tour Around Anna Maria Island
See all activities in Longboat Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.