Longboat Key Vacations from $440

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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.
Saddlebrook Resort
Hotel Tampa Riverwalk
The Residences at Siesta Key Beach by Hyatt Vacation Club
Legacy Hotel at IMG Academy
Kompose Boutique Hotel
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Discover the most popular places to visit in Longboat Key

What to do 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
$1,154 nightly
The price is $1,304 total per night from Jan 18 to Jan 19
$1,304 total
Jan 18 - Jan 19
Total with taxes and fees
9.8/10 Exceptional! (60 reviews)
Best of the best ! it was incredible! i want to go back again🙌♥️

Reviewed on Jan 12, 2026

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
$269 nightly
The price is $304 total per night from Jan 19 to Jan 20
$304 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Staff was great

Reviewed on Jan 5, 2026

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
$549 nightly
The price is $620 total per night from Jan 19 to Jan 20
$620 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (688 reviews)
Everything Perfect!

Reviewed on Dec 11, 2025

The Resort at Longboat Key Club
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

Things to do in and around Longboat Key

Longboat Key is perfect for beach and family vacations, offering a mix of outdoor adventures and quiet beaches. Visitors can explore local shopping centers and resorts while enjoying various entertainment attractions. Whether you're looking to relax on the sand or engage in fun activities, Longboat Key provides a charming getaway with something for everyone.

Shopping

For a charming shopping experience, visit Bridge Street, just 4 miles away, offering a mix of local businesses and family-friendly vibes. West Coast Surf Shop, 7 miles from Longboat Key, is perfect for surf enthusiasts. If you're up for a drive, check out the Red Barn Flea Market Plaza, 8 miles away, for unique finds.

Recreation

At Aluna Wellness Center & Spa, indulge in rejuvenating body treatments that promote relaxation and wellness, just 5 miles from Longboat Key. For a cultural experience, enjoy performances at Van Wezel Performing Arts Hall, located 8 miles away, offering a blend of entertainment and romance.

Adventure

Experience thrilling underwater adventures with Blue Water Explorers, located 4 miles from Longboat Key, where you can explore vibrant marine life. For a fun-filled day on the water, AMI Paddleboard Adventures, 7 miles away, offers paddleboarding in a stunning outdoor setting. Enjoy tennis at the Longboat Key Public Tennis Center, right in the area.

Nightlife

Longboat Key offers a relaxed nightlife with stunning beach views. Enjoy cocktails at the charming Beach House Restaurant, or unwind at the lively Mar Vista Dockside Restaurant and Pub. For a more upscale vibe, check out the elegant dining at the Chart House, perfect for a memorable evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Longboat Key

Longboat Key, Florida, is a fantastic destination for beach lovers and families, offering a blend of outdoor activities and cultural experiences. Visitors can enjoy attractions like Lido Key Beach, local gyms, and marina access. With its beautiful beaches and nearby modern amenities, Longboat Key is perfect for those seeking relaxation or adventure. Explore the scenic landscapes and enjoy the vibrant community, making it an ideal getaway for travelers of all types.

  • IMG Academy: A premier sports training destination, IMG Academy offers a unique opportunity to witness elite athletes in action. With state-of-the-art facilities, you can enjoy a range of sports events or even participate in youth camps, making it a hub for sports enthusiasts and aspiring athletes alike.
  • Lido Beach: This stunning beach boasts soft, white sands and vibrant beach vibes, making it perfect for sunbathing, swimming, or beachcombing. With its picturesque sunsets and inviting waters, Lido Beach is an ideal spot for relaxation and family fun.
  • St. Armands Circle: A bustling hub of shopping and dining, St. Armands Circle offers a chic urban atmosphere. Explore unique boutiques, indulge in gourmet cuisine, and enjoy live entertainment, all within a vibrant, walkable environment that captures the essence of coastal city life.

Best time to go to Longboat Key

The best time to visit Longboat Key can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Longboat Key falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature in Longboat Key falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
February65.5°F (18.6°C)No RainMostly SunnyAverageSlightly High
March68.4°F (20.2°C)Light RainMostly SunnyModerately HighSlightly High
April73.8°F (23.2°C)Light RainMostly SunnyModerately HighSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Moderate RainMostly SunnyModerately HighAverage
August83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Moderate RainMostly SunnyAverageSlightly Low
October77.0°F (25.0°C)Light RainMostly SunnyModerately LowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately LowSlightly Low
December66.4°F (19.1°C)Light RainMostly SunnyModerately LowAverage

Tips to save on your trip to Longboat Key

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Longboat Key during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $440 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.

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