Longboat Key Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

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 S$1,223 per night from 24 Jun to 25 Jun
S$1,223
24 Jun - 25 Jun
includes taxes & fees
9.6/10 Exceptional! (24 reviews)
"This property is breathtakingly beautiful!"

Reviewed on 10 Jun, 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 S$433 per night from 30 Jun to 1 Jul
S$433
30 Jun - 1 Jul
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Very nice property, we loved walking down to the beautiful beach. It was very quiet and peaceful even though there were many people there. Great staff - super friendly and efficient - had a great stay. Would highly recommend!"

Reviewed on 9 Jun, 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 S$687 per night from 23 Jun to 24 Jun
S$687
23 Jun - 24 Jun
includes taxes & fees
8.8/10 Excellent! (644 reviews)
"From the moment we arrived we were greeted with respect and enthusiasm to make sure our time here was great. Staff was awesome."

Reviewed on 12 Jun, 2025

The Resort at Longboat Key Club
See all 860 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 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.

What to do in Longboat Key

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

Fly Above Water, eFoil Adventure in Sarasota

S$321
per adult
Fly Above Water, eFoil Adventure in Sarasota
Half Day Eco and Dolphin Boat Tour in Siesta Key

Half Day Eco and Dolphin Boat Tour in Siesta Key

S$1,003
per traveller
Half Day Eco and Dolphin Boat Tour in Siesta Key
Fly Above The Sea on a Flite Scooter

Fly Above Ocean Adventure on a Flite Scooter!

S$321
per adult
Fly Above Ocean Adventure on a Flite Scooter!
See all activities in Longboat Key

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.