Longboat Key Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Longboat Key

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 19.691.210 ₫ per night from 10 Aug to 11 Aug
19.691.210 ₫
24.182.069 ₫ total
10 Aug - 11 Aug
includes taxes & fees
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 6.283.310 ₫ per night from 9 Aug to 10 Aug
6.283.310 ₫
8.288.448 ₫ total
9 Aug - 10 Aug
includes taxes & fees
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 12.312.657 ₫ per night from 23 Jul to 24 Jul
12.312.657 ₫
15.396.597 ₫ total
23 Jul - 24 Jul
includes taxes & fees
9/10 Wonderful! (727 reviews)
"Todo excelente , tanto las instalaciones como el personal de servicio, la playa bastante buena, para el año que viene volvere"

Reviewed on 17 Jul 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 snorkelling gear to discover abundant marine life in this tranquil Gulf Coast retreat.
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Frequently asked questions

How much does a Longboat Key holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday 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 holiday for longer.
Is it worth booking a holiday 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 holiday.
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 holiday package well in advance.
Is it cheaper to book a Longboat Key holiday as a package?
You can enjoy significant savings on your next Longboat Key retreat by booking a personalised holiday 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 holiday 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 favourite 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 customised Longboat Key holiday package.

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