Longboat Key Vacations

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Find the Best Longboat Key Vacation Packages

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 ￥38,840 per night from Aug 9 to Aug 10
￥38,840
￥51,234 total
Aug 9 - Aug 10
includes taxes & fees
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 ￥121,720 per night from Aug 10 to Aug 11
￥121,720
￥149,480 total
Aug 10 - Aug 11
includes taxes & fees
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 ￥76,166 per night from Aug 13 to Aug 14
￥76,166
￥95,244 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (731 reviews)
"Beautiful property and very helpful staff. I checked in early and they were able to accommodate me."

Reviewed on Jul 20, 2026

The Resort at Longboat Key Club
See all 881 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.

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)
This secluded island off Longboat Key is only accessible by boat, offering pristine sandbars and crystal-clear waters. Bring snorkeling gear to discover abundant marine life in this tranquil Gulf Coast retreat.
See properties

What to do in Longboat Key

Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

￥9,590
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

￥17,717
per adult
100% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

￥8,940
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?
Offering excellent value package deals 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.

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