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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (9 reviews)
Very conveniently located. Great room size and comfortable bed.

Reviewed on Aug. 5, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
per person
Oct 26 - Oct 31
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (274 reviews)
Beachfront location is great!!

Reviewed on Jul. 22, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (557 reviews)
Everything was great. Beautiful view from our room. Surer clean. For sure will stay again.

Reviewed on Aug. 4, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,046 reviews)
Everything is great. Lacking food on the property and roof top bar doesn’t exist anymore

Reviewed on Aug. 1, 2025

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (859 reviews)
It is difficult to get the bill at the end of your stay emailed to you, but the stay and property was really nice. The young waitress was absolutely amazing with impeccable customer service. Loved the atmosphere and the beds are really spacious and not like other hotels that claim they gave you a queen and it looks like a double. I just wished room service gave the room a proper cleaning while we were there at least once or twice for the 8 nights we stayed and not just straightening up the room.

Reviewed on Aug. 5, 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 $963 per night from Aug 25 to Aug 26
CA $963
CA $1,173 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (35 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 $343 per night from Sep 1 to Sep 2
CA $343
CA $450 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Beautiful hotel very good services bed comfort"

Reviewed on Aug. 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 $552 per night from Sep 1 to Sep 2
CA $552
CA $686 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (661 reviews)
Great exclusive place
"At $500 / night the place had better be 5* and more !! Service was great !!"

Reviewed on Aug. 2, 2025

The Resort at Longboat Key Club
See all 846 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

Robinson Preserve Mangrove Tour

Robinson Preserve Mangrove Tour

CA $75
per adult
Robinson Preserve Mangrove Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

CA $89
per adult
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

CA $82
per adult
90% of travellers recommend
Anna Maria Island and Bradenton: Sunset Kayak Dolphin 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 $575 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.