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.
CW Hotel

CW Hotel

4 out of 5
Price was CA $1,537, price is now CA $1,068 per person
CA $1,068
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,981, price is now CA $1,195 per person
CA $1,195
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
The location was convenient, just a short walk to the beach and there are plenty of options for good food. The hotel was beautiful!

Reviewed on Jul 6, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,509, price is now CA $1,554 per person
CA $1,554
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,057 reviews)
It’s a very small lobby when you check in with only one person checking people in and it can take a very long time. In addition to that there are only two elevators that are also in the lobby so it can become a tight squeeze with everybody, trying to get their belongings in and out and people trying to check in. Overall, we had a good time and I can’t complain too much.

Reviewed on Jul 5, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,810, price is now CA $1,891 per person
CA $1,891
per person
Sep 26 - Oct 3
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (561 reviews)
10/10 would recommend this property. Clean, freindly staff, complimentary coffee bar, and great location are just some of the perks of staying here. The rooftop bar and pool is a nice way the wind down your day that included a comp glass of champagne amd views of awesome sunsets. The property also offered access to free beach chairs and umbrellas for use on the beach which is a huge plus in my book. Numerous stores and restaurants well within walking distance of the hotel. So if your looking for a nice hotel while visiting CWB, look no further. You will not be disappointed. We will definitely be returning on our next beach vacation.

Reviewed on Jul 1, 2026

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Price was CA $1,847, price is now CA $1,293 per person
CA $1,293
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (794 reviews)
Wrong room category was sold to me…property blamed Expedia for that…my anniversary surprise gift was ruined and neither front desk nor General Manager cared to address our situation and never responded to our call…will never go back!!!!

Reviewed on Jul 5, 2026

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Longboat Key Hotel Deals

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 $354 per night from Jul 13 to Jul 14
CA $354
CA $464 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"We really enjoyed our stay here. We traveled with our 80 year old family member and everyone went out of their way to make her comfortable. The food was spectacular, and the cocktails were delicious. The walk to the beach is very easy and the pool was wonderful."

Reviewed on Jul 5, 2026

Zota Beach Resort
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 $1,177 per night from Aug 5 to Aug 6
CA $1,177
CA $1,435 total
Aug 5 - Aug 6
includes taxes & fees
9.8/10 Exceptional! (83 reviews)
"Staff in restaurants were somewhat accommodating. We asked to change our reservation from 2 to 4 people in the Riva restaurant. We were informed they could only take us at 8:10. We said ok, then the manager of Riva said no, not until 9:00 is there an open table. Then the concierge informed me he ..."

Reviewed on Jul 5, 2026

The St. Regis Longboat Key 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 $677 per night from Jul 25 to Jul 26
CA $677
CA $846 total
Jul 25 - Jul 26
includes taxes & fees
9/10 Wonderful! (724 reviews)
"The hotel was clean and the staff was friendly. The problem we had was that the resort had 7 buildings and one pool. So unless you got there early you were forced to go to the beach. Also the lounge chairs at the pool were on top of each other with other people right next to you so there was no privacy. ..."

Reviewed on Jun 29, 2026

The Resort at Longboat Key Club
See all 880 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.
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Stay near popular Longboat Key attractions

A lake with clear water, surrounded by dense green trees and a partly cloudy sky.
Photo by throwingsofas
Open Photo by throwingsofas

Jewfish Key

9.0/10 (34 reviews)
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.
See properties

What to do in Longboat Key

Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $82
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
Sarasota Guided Mangrove Tunnel Kayak Tour

Sarasota Guided Mangrove Tunnel Kayak Tour

CA $84
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $76
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee 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 $1,068 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.

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