How much does a Longboat Key vacation package cost?

Offering excellent value package deals from $355 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?

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. 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. 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. 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. 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. 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.

Longboat Key Vacation Packages 2025/2026 from $365

Name: The St. Regis Longboat Key Resort
Price range: $852 total
Rating: 9.6

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.

Clearwater Suites

Save 100% on your flight

$355

per person

Nov 15 - Nov 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (12 reviews)

The property is spacious, beds are comfortable, staff are friendly. Located just a block away from the beach. Guest service desk provided a welcome snack basket. The one downside is that the bathroom could be cleaned better. Overall it’s a great place to stay in.

Reviewed on Aug 16, 2025

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$593

per person

Oct 9 - Oct 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,000 reviews)

The staff was very nice and helpful. The shuttle would take you anywhere within 3 miles. Pool was nice and the hotel was quiet.

Reviewed on Aug 12, 2025

FUSION Resort Waterfront Suites

Save 100% on your flight

$707

per person

Oct 2 - Oct 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,049 reviews)

Rooms are 2 bedroom suites. Full size kitchen makes an extended stay more affordable. Extremely pet friendly environment.

Reviewed on Aug 8, 2025

Ocean Club Treasure Island Hotel

Save 100% on your flight

$737

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (598 reviews)

Love this place! Rooms are excellent. Please note the lobby is a tiny check in area but the rooms are amazing.

Reviewed on Aug 20, 2025

Wyndham Grand Clearwater Beach

Save 100% on your flight

$907

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (2,549 reviews)

Fourth time here and it still is the best. Great location close to beach and walk to many restaurants and shops. Pool is fun and the service was impeccable by everyone. Get the grouper bites with remoulade sauce at the pool you won't be disappointed. My favorite place in Florida.

Reviewed on Aug 23, 2025

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Longboat Key Hotel Deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive, Longboat Key, FL

Fully refundableReserve now, pay when you stay

$754 nightly

$852 total

Aug 24 - Aug 25

Total with taxes and fees

9.6/10 Exceptional! (39 reviews)

"Amazing"

Reviewed on Jul 22, 2025

Zota Beach Resort

4711 Gulf of Mexico Dr, Longboat Key, FL

Fully refundableReserve now, pay when you stay

$289 nightly

$327 total

Aug 24 - Aug 25

Total with taxes and fees

8.8/10 Excellent! (1,001 reviews)

"Very friendly staff. Clean and well kept. High value for the price."

Reviewed on Aug 17, 2025

The Resort at Longboat Key Club

220 Sands Point Road, Longboat Key, FL

Fully refundableReserve now, pay when you stay

$441 nightly

$498 total

Sep 1 - Sep 2

Total with taxes and fees

8.8/10 Excellent! (664 reviews)

"Excellent customer service. Gorgeous property and beach. Will stay here again."

Reviewed on Aug 8, 2025

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.

Things to do near Longboat Key

Longboat Key is an ideal destination for beach lovers and families, offering a mix of shopping centers and recreational areas. Visitors can enjoy outdoor adventures, explore the tranquil surroundings, and unwind on the quiet beaches. With a variety of entertainment attractions, Longboat Key provides a perfect blend of relaxation and fun for everyone.

Shopping

For a delightful shopping experience in Longboat Key, visit Bridge Street, only 4 miles away, offering a charming atmosphere. West Coast Surf Shop, located 7 miles away, caters to surf enthusiasts. If you're up for a drive, check out the Red Barn Flea Market Plaza, 8 miles away, for unique finds.

Recreation

LECOM Park offers an energetic atmosphere for sports enthusiasts, perfect for catching a game or enjoying outdoor activities. Aluna Wellness Center & Spa provides a tranquil retreat with rejuvenating treatments designed for ultimate relaxation. For culture and entertainment, the Van Wezel Performing Arts Hall showcases captivating performances in a charming setting.

Adventure

At H2O Watersportz, located 4 miles from Longboat Key, you can dive into thrilling water sports, soaking up the sun and adrenaline. Blue Water Explorers, also 4 miles away, offers a unique underwater adventure, perfect for exploring marine life. AMI Paddleboard Adventures, 7 miles away, allows you to paddle through scenic waters.

Nightlife

For a relaxed nightlife experience in Longboat Key, explore local favorites like the Longboat Key Club and the Mar Vista Dockside Restaurant. Enjoy live music at the Beach House or sip cocktails at the nearby bars, all while soaking in the stunning waterfront views.

*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 an ideal destination for beach, family, and city-themed vacations. Visitors can enjoy stunning beaches, explore marinas, and discover modern attractions, all while experiencing the local culture and outdoor activities. Nearby, Lido Key offers additional beach access, and there are gyms and patios in Longboat Key for fitness and dining. With its perfect blend of leisure and adventure, Longboat Key promises a memorable getaway for every traveler.

IMG Academy: Located 4 miles from Longboat Key, IMG Academy offers a unique experience for sports enthusiasts and aspiring athletes. This renowned sports training facility features state-of-the-art facilities and professional coaching, making it an ideal place to train or watch elite athletes in action.
Lido Beach: Just 9 miles away, Lido Beach is perfect for sunbathing, swimming, and enjoying beach vibes. With its soft sand and crystal-clear waters, it's a relaxing spot to soak up the sun or partake in water sports.
St. Armands Circle: About 8 miles from Longboat Key, St. Armands Circle is a vibrant shopping and dining destination. Enjoy the city vibes as you explore boutique shops, art galleries, and a variety of restaurants, making it a great place for a leisurely stroll.

Best time to go to Longboat Key

The best time to visit Longboat Key is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Average	Average
February	65.5°F (18.6°C)	No Rain	Mostly Sunny	Average	Slightly High
March	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
April	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
May	78.1°F (25.6°C)	Light Rain	Mostly Sunny	Average	Average
June	82.0°F (27.8°C)	Light Rain	Mostly Sunny	Average	Average
July	83.1°F (28.4°C)	Moderate Rain	Mostly Sunny	Moderately High	Average
August	83.5°F (28.6°C)	Moderate Rain	Mostly Sunny	Average	Average
September	81.5°F (27.5°C)	Moderate Rain	Mostly Sunny	Average	Slightly Low
October	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	70.5°F (21.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	66.4°F (19.1°C)	Light Rain	Mostly Sunny	Moderately Low	Average

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 during the off-peak season (typically September to November) for more affordable package holidays to Longboat Key.
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.