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.
The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,415, price is now CA $845 per person
CA $845
per person
Oct 6 - Oct 10
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (443 reviews)
Excellent place no word to explain how perfect everything was. We definitely go there from now on

Reviewed on Aug. 24, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $2,252, price is now CA $1,149 per person
CA $1,149
per person
Oct 6 - Oct 13
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (598 reviews)
I love it, all staff super nice Beautiful place, clean, awesome beach Thanks

Reviewed on Aug. 24, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $1,895, price is now CA $1,035 per person
CA $1,035
per person
Oct 6 - Oct 13
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,053 reviews)
The room was fantastic with a big wrap around balcony. Even though the weather did not cooperate, we all enjoyed chilling on the balcony with many trips to the pool. Beach was great. My only disappointment was they did not have any type of grill anywhere. I brought some really expensive steaks, burgers,hot dogs, which we had to cook in a pan. The staff was fantastic and made sure we had everything we needed

Reviewed on Aug. 24, 2025

Inn on the Beach

Inn on the Beach

2.5 out of 5
Pass-a-Grille
Price was CA $2,584, price is now CA $1,464 per person
CA $1,464
per person
Oct 6 - Oct 13
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (330 reviews)
Our go-to location in St. Pete! Steps from the beach. Very well maintained property and great staff. Highest recommendations!

Reviewed on Aug. 25, 2025

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,897, price is now CA $1,142 per person
CA $1,142
per person
Oct 6 - Oct 13
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (467 reviews)
The staff were the best part of the property. It wasn't super convenient to go to the main office for anything because of having to cross a busy road and walking a block and parking was limited so we couldn't park there to use the pool or amenities. The room itself was clean and we appreciated the view on the bay but the bed wasn't comfortable at all. Overall, it was a decent value but the office being so far offsite with the better pool, beach access and bar but no parking for guests of the other hotels was a real detractor for us.

Reviewed on Aug. 27, 2025

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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
Fully refundableReserve now, pay when you stay
The price is CA $961 per night from Sep 1 to Sep 2
CA $961
CA $1,172 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (39 reviews)
"Amazing"

Reviewed on Jul. 22, 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 $342 per night from Sep 1 to Sep 2
CA $342
CA $449 total
Sep 1 - Sep 2
includes taxes & fees
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 $551 per night from Sep 1 to Sep 2
CA $551
CA $685 total
Sep 1 - Sep 2
includes taxes & fees
The Resort at Longboat Key Club
See all 858 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
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What to do in Longboat Key

Fly Above The Sea on a Flite Scooter

Fly Above Ocean Adventure on a Flite Scooter!

CA $344
per adult
Fly Above Ocean Adventure on a Flite Scooter!
Picture 1 for Activity Fly Above Water, eFoil Adventure in Sarasota

Fly Above Water, eFoil Adventure in Sarasota

CA $344
per adult
Fly Above Water, eFoil Adventure in Sarasota
Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

CA $76
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
See all activities in Longboat Key

Frequently asked questions

How much does a Longboat Key vacation package cost?
You'll find cheap prices from CA $845 on Expedia for your Longboat Key getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Longboat Key costs.
What are the cheapest months to go to Longboat Key?
If you'd like to book a cheap Longboat Key vacation package, consider planning a trip in January, August and December. You'll usually find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Longboat Key?
To get the most out of a Longboat Key vacation, we suggest booking for 3 days. Split your time between discovering Jewfish Key, Anna Maria Sound and other must-see attractions, in addition to exploring neighbourhoods like Bayshore Gardens and South Bradenton. If you've got some time to spare, include a day trip or tour in your Longboat Key vacation itinerary.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has all the ingredients you need for a fantastic break — coastal beaches, views and watersports are just the start. Whether you want to visit attractions like Jewfish Key and Cannons Marina, or take the path less travelled, there's plenty to see and do on your Longboat Key vacation.
How to find the best Longboat Key package deals?
Bagging a cheap Longboat Key package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Longboat Key package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Longboat Key vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Longboat Key trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Longboat Key?
If you're considering an impromptu Longboat Key vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Longboat Key?

  1. Choose your dates: The things you plan to do in Longboat Key and your favourite season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will probably be the largest expense during your trip to Longboat Key.
  3. Decide how long to go for: Now that you're up to speed on Longboat Key, you can work out the ideal length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Longboat Key vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.