Longboat Key Vacations
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Find the Best Longboat Key Vacation Packages
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
￥117,039
￥143,732 total
Sep 8 - Sep 9
includes taxes & fees
9.8/10 Exceptional! (93 reviews)
"Perfecto"
Reviewed on Sep 4, 2026
Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
Fully refundableReserve now, pay when you stay
￥32,658
￥43,967 total
Sep 8 - Sep 9
includes taxes & fees
The Resort at Longboat Key Club
220 Sands Point Road Longboat Key FL
Fully refundableReserve now, pay when you stay
￥70,161
￥88,111 total
Sep 8 - Sep 9
includes taxes & fees
9/10 Wonderful! (762 reviews)
"Children crying was annoying but everything else was something a cut above and will never forget"
Reviewed on Aug 29, 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
Photo by throwingsofas
Jewfish Key
9.0/10 (34 reviews)
This secluded island off Longboat Key is only accessible by boat, offering pristine sandbars and crystal-clear waters. Bring snorkeling gear to discover abundant marine life in this tranquil Gulf Coast retreat.
Quick Point Nature Reserve
8.4/10 (43 reviews)
This 34-acre coastal preserve showcases Florida's natural beauty through mangrove forests and tidal lagoons. Stroll the scenic boardwalks at low tide for prime birdwatching and wildlife observation opportunities.
Harborside Golf Course at Longboat Key Club
9.0/10 (40 reviews)
Bordered by Sarasota Bay, this 27-hole golf course challenges players with tight fairways and strategic water hazards. Reserve a morning tee time to experience the pristine Platinum Paspalum greens at their best.
Links on Longboat
8.6/10 (62 reviews)
This seaside links-style course challenges golfers with ocean breezes and water hazards on most holes. Enjoy the panoramic views of palm-lined fairways while egrets and herons add to the serene atmosphere.
Longboat Key Public Tennis Center
This well-maintained tennis center offers pristine courts in a picturesque Florida setting. Reserve your morning court time and bring equipment for a perfect match under the gentle winter sunshine.
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
Anna Maria Island & Bradenton Beach Parasailing Tour
￥17,450
per adult
100% of travellers recommend
Siesta Key Electric Bike Sunset Tour
￥11,435
per adult
96% of travellers recommend
Clear Kayak Glass Bottom Day Tour - Anna Maria Island
￥10,406
per adult
Frequently asked questions
How much does a Longboat Key vacation package cost?
Offering excellent value package deals 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?
January, August and December are the best times to search for cheap Longboat Key vacation 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 vacation for longer.
Is it worth booking a vacation 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 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 favorite season and the available activities will also help you decide when to visit Longboat Key.
- 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.
- 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.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Longboat Key vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
