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.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 18
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,034 reviews)
The property was quiet, clean and comfortable. The customer service was professional and above average. I would not hesitate to book again. Two bedrooms and two bathrooms, living room and full kitchen was plenty room for husband and I. Only stayed one night but wished it was longer.

Reviewed on Jun. 26, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
We enjoyed our stay here and definitely will come again in the future Clean, well maintained, staffs are nice. Easy access to beach.

Reviewed on Jul. 6, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 18
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (421 reviews)
Clean nice I am use to big hotels Very nice staff and helpful pool is little small besides that good

Reviewed on Jul. 6, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
7.8/10 Good! (9 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun. 10, 2025

The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Port Tampa City
Save 100% on your flight
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sarasota (SRQ)
9/10 Wonderful! (149 reviews)
The insulation was awful. We could hear everything going on above us. It sounded like they were stomping and moving furniture. When the air conditioner kicked on you had to turn the tv up quite a bit to hear it

Reviewed on Jun. 10, 2025

Ready to book your vacation to Longboat Key?

 

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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 $1,073 per night from Jul 13 to Jul 14
CA $1,073
CA $1,297 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"Amazing that's the only thing anyone needs to know about spending time here"

Reviewed on Jun. 29, 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 $333 per night from Aug 3 to Aug 4
CA $333
CA $438 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"I loved how clean and quiet this place is. Being a small building complex helps control the amount of people. The beaches are beautiful. Love how pet friendly it is, but also keep all the rooms neat and clean and not smelling like animals."

Reviewed on Jul. 3, 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 $551 per night from Jul 8 to Jul 9
CA $551
CA $684 total
Jul 8 - Jul 9
includes taxes & fees
8.8/10 Excellent! (646 reviews)
"Great experience."

Reviewed on Jun. 21, 2025

The Resort at Longboat Key Club
See all 861 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

What to do in Longboat Key

Picture 1 for Activity Fly Above Water, eFoil Adventure in Sarasota

Fly Above Water, eFoil Adventure in Sarasota

CA $343
per adult
Fly Above Water, eFoil Adventure in Sarasota
Efoil Watersport Experience in Sarsota

Fly Above Water Adventure in Sarasota. A Must Experience!

CA $343
per adult
Fly Above Water Adventure in Sarasota. A Must Experience!
Fly Above The Sea on a Flite Scooter

Fly Above Ocean Adventure on a Flite Scooter!

CA $343
per adult
Fly Above Ocean Adventure on a Flite Scooter!
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 $773 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.