Longboat Key Vacations

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Find the Best Longboat Key Vacation Packages

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
The price is SAR 3,147 per night from May 4 to May 5
SAR 3,147
SAR 3,790 total
includes taxes & fees
4 May - 5 May
9.8/10 Exceptional! (17 reviews)
"Need a better system for assigning chairs around adult pool...also beach lounger experience needs to be upgraded to be more luxurious probably sun beds with shade...also first day adult pool too warm waterfall was offsecond day waterfall on but was ice cold soadult pool was a bit cool must do better ..."

Reviewed on 23 March 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 SAR 1,122 per night from May 4 to May 5
SAR 1,122
SAR 1,437 total
includes taxes & fees
4 May - 5 May
8.8/10 Excellent! (1,000 reviews)
"Nice"

Reviewed on 31 March 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 SAR 2,022 per night from Apr 27 to Apr 28
SAR 2,022
SAR 2,454 total
includes taxes & fees
27 Apr - 28 Apr
8.8/10 Excellent! (639 reviews)
"Absolutely beautiful clean rooms and great service staff. Dean is the man to talk to. He went above and beyond to make sure we were taken care of."

Reviewed on 27 March 2025

The Resort at Longboat Key Club
See all 869 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.

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 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.

Discover the most popular places to visit in Longboat Key

Jewfish Key is a private island that we kayaked around. We saw a couple dolphins playing nearby too, but the main attraction to the public is large sandbar nearby. We rented our kayaks from a place called Kayak Jack's. They were great! You pick a drop-off location and specify a time and your kayaks will be awaiting you, ready for launch! http://www.kayak-jacks.com “You choose the location, We bring the Fun!”

Jewfish Key

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.

Jewfish Key

Harborside Golf Course at Longboat Key Club

Enjoy a round of golf in Longboat Key at Harborside Golf Course at Longboat Key Club. Wander the beautiful beaches or discover the area's beautiful sunsets.

Harborside Golf Course at Longboat Key Club

Islandside Golf Course at Longboat Key Club

Enjoy a round of golf in Longboat Key at Islandside Golf Course at Longboat Key Club. Wander the beautiful beaches or discover the area's beautiful sunsets.

Islandside Golf Course at Longboat Key Club