Longboat Key Vacation Packages
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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.
Top Longboat Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,055
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (1,190 reviews)
Amazing g
Place great bar and staff
Horrible fiod menu all frozen and processed no fruits yogurts or salads for sale
Reviewed on Sep 12, 2026
Ready to book your vacation to Longboat Key?
Longboat Key Hotel Deals
Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
Fully refundableReserve now, pay when you stay
CA $290
CA $390 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Perfect get away. Quiet relaxing"
Reviewed on Sep 12, 2026
The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive Longboat Key FL
Fully refundableReserve now, pay when you stay
CA $1,039
CA $1,276 total
Sep 14 - Sep 15
includes taxes & fees
9.8/10 Exceptional! (93 reviews)
"Perfecto"
Reviewed on Sep 4, 2026
The Resort at Longboat Key Club
220 Sands Point Road Longboat Key FL
Fully refundableReserve now, pay when you stay
CA $609
CA $766 total
Sep 14 - Sep 15
includes taxes & fees
9/10 Wonderful! (763 reviews)
"Very nice upscale place. Just a little pricey."
Reviewed on Sep 9, 2026
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
Longboat Key Beaches
9.6/10 (394 reviews)
Why not spend a lazy afternoon at Longboat Key Beaches during your trip to Longboat Key? Wander the beautiful beaches in this relaxing area.
Photo by throwingsofas
Jewfish Key
9.0/10 (34 reviews)
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.
Cannons Marina
8.6/10 (47 reviews)
Explore the waterfront in Longboat Key with a trip to Cannons Marina. Wander the beautiful beaches and seaside in the area.
Quick Point Nature Reserve
8.4/10 (43 reviews)
Enjoy the beautiful sunsets and explore Quick Point Nature Reserve, a lovely green space in Longboat Key. While you're in the area, stroll along the beautiful beaches.
Harborside Golf Course at Longboat Key Club
9.0/10 (40 reviews)
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.
Links on Longboat
8.6/10 (62 reviews)
Enjoy a round of golf in Longboat Key at Links on Longboat. Wander the beautiful beaches or discover the area's beautiful sunsets.
Longboat Key Public Tennis Center
Catch an event at Longboat Key Public Tennis Center during your trip to Longboat Key.
Shoppes of Bay Isles
8.4/10 (8 reviews)
You can search for that perfect souvenir at Shoppes of Bay Isles during your trip to Longboat Key. Stroll along the marina or discover the area's beautiful sunsets.
What to do in Longboat Key
Sarasota - Clear Kayak LED Night Glass Bottom Tour
CA $90
per adult
78% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
CA $76
per adult
100% of travellers recommend
Frequently asked questions
How much does a Longboat Key vacation package cost?
You'll find cheap prices from CA $802 on Expedia for your Longboat Key getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Longboat Key costs.
What are the cheapest months to go to Longboat Key?
If you'd like to book a cheap Longboat Key vacation package, consider planning a trip in January, August and December. You'll usually find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Longboat Key?
To get the most out of a Longboat Key vacation, we suggest booking for 3 days. Split your time between discovering Jewfish Key, Anna Maria Sound and other must-see attractions, in addition to exploring neighbourhoods like Bayshore Gardens and South Bradenton. If you've got some time to spare, include a day trip or tour in your Longboat Key vacation itinerary.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has all the ingredients you need for a fantastic break — coastal beaches, views and watersports are just the start. Whether you want to visit attractions like Jewfish Key and Cannons Marina, or take the path less travelled, there's plenty to see and do on your Longboat Key vacation.
How to find the best Longboat Key package deals?
Bagging a cheap Longboat Key package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Longboat Key package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Longboat Key vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Longboat Key trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Longboat Key?
If you're considering an impromptu Longboat Key vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Longboat Key?
- Choose your dates: The things you plan to do in Longboat Key and your favourite season will help you decide when to get away.
- Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will probably be the largest expense during your trip to Longboat Key.
- Decide how long to go for: Now that you're up to speed on Longboat Key, you can work out the ideal length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Longboat Key vacation package that brings all your bookings together.
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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.
