Longboat Key Vacations from $305

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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.

The Latest Longboat Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 21
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
Staff was very friendly. Property was clean and well taken care . Right on the beach, volleyball court and a nice bar near pool.

Reviewed on Jul 2, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
7.8/10 Good! (9 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun 10, 2025

The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
9.2/10 Wonderful! (901 reviews)
Beautiful and close to Beach and bay Staff was amazing

Reviewed on Jun 29, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 14
found 19 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
We had a room with a balcony facing the ocean. The staff were excellent and the room and facilities were good. This hotel is a more affordable option if you want easy beach access on Gulf Blvd. in St. Pete. Make arrangements if you are checking in late. The front office closes at 7pm and doesn't reopen until 8am. Overall, this was good value for the money.

Reviewed on Jun 25, 2025

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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

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

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

What to do in Longboat Key

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

Fly Above Water, eFoil Adventure in Sarasota

$250
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

$780
per traveler
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!

$250
per adult
Fly Above Ocean Adventure on a Flite Scooter!
See all activities in Longboat Key

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
$844 nightly
The price is $954 total per night from Jul 13 to Jul 14
$954 total
Jul 13 - Jul 14
Total includes taxes and fees
9.6/10 Exceptional! (27 reviews)
"Amazing that's the only thing anyone needs to know about spending time here"

Reviewed on Jun 29, 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
$285 nightly
The price is $322 total per night from Aug 3 to Aug 4
$322 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Very sleek modern hotel. Nice and quiet - good breakfast option. Beautiful beach"

Reviewed on Jul 2, 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
$445 nightly
The price is $503 total per night from Jul 6 to Jul 7
$503 total
Jul 6 - Jul 7
Total includes taxes and fees
8.8/10 Excellent! (646 reviews)
"Great experience."

Reviewed on Jun 21, 2025

The Resort at Longboat Key Club
See all 862 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.

Find the Best Longboat Key Vacation Packages

Longboat Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sarasota-Bradenton Intl. Airport (SRQ)
Population
7,300
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Coquina Beach, Anna Maria Beach and Cortez Beach

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Frequently asked questions

How much does a Longboat Key vacation package cost?
Offering excellent value package deals from $305 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?
If you're looking to book a cheap Longboat Key vacation package, consider traveling in September, October and November. You'll generally find lower prices on flights and hotels during these quieter months --- ideal for travelers wishing to save money.
How many days is enough for Longboat Key?
The ideal length of your Longboat Key vacation depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has everything you need for an awesome trip --- coastal beaches, views and watersports are just the start. Whether you'd like to check out sights such as Jewfish Key and Cannons Marina, or venture off the beaten track, there's plenty to do 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 preferred time of year and the activities on offer will also help you decide when to visit Longboat Key.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Longboat Key. Then, choose a property that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Use Expedia's trip planning tool to explore Longboat Key: Research every aspect of your trip to Longboat Key with this handy planner. Invite friends or family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Work out your trip length: Think about how long you'd like to spend discovering Longboat Key. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Longboat Key vacation package.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some incredible things to do in Longboat Key in Longboat Key. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Longboat Key vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Longboat Key vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.