Longboat Key Holidays & Package Deals

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Longboat Key Holiday

Our pick of the best Longboat Key Hotel Deals

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Fully refundableReserve now, pay when you stay

NZ$491

21 Sept - 22 Sept

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

"AC was blasting us. We slept on the couch in rm# 224. Shower floor was not in good shape. Looked dirty and quickly prepared. Staff was first class. Duncan Boynton"

Reviewed on 17 Sept 2026

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

Fully refundableReserve now, pay when you stay

NZ$1,605

30 Sept - 1 Oct

includes taxes & fees

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Fully refundableReserve now, pay when you stay

NZ$964

21 Sept - 22 Sept

includes taxes & fees

9/10 Wonderful! (765 reviews)

"Wonderful beach place to stay"

Reviewed on 18 Sept 2026

See all 899 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.

Stay near popular Longboat Key attractions

A coastal cityscape with a bridge, marina, and lush greenery.

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.

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A lake with clear water, surrounded by dense green trees and a partly cloudy sky.

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 snorkelling gear to discover abundant marine life in this tranquil Gulf Coast retreat.

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A white heron standing on a tree branch with Spanish moss.

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.

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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.

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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.

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Longboat Key Public Tennis Center

This well-maintained tennis centre 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.

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Shoppes of Bay Isles

8.4/10 (8 reviews)

You can browse for the perfect souvenirs at Shoppes of Bay Isles during your visit to Longboat Key. Stroll along the marina or discover the area's beautiful sunsets.

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What to do in Longboat Key

Manatee Discovery Anna Maria Island

NZ$92

per adult

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

NZ$92

per adult

100% of travellers recommend

Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

NZ$119

per adult

96% of travellers recommend

See all activities in Longboat Key

Frequently asked questions

How much does a Longboat Key holiday package cost?

Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday 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 holiday for longer.

Is it worth booking a holiday 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 holiday.

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 holiday package well in advance.

Is it cheaper to book a Longboat Key holiday as a package?

You can enjoy significant savings on your next Longboat Key retreat by booking a personalised holiday 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 holiday 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 favourite 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 customised Longboat Key holiday package.

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Activities in Palmetto

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

Longboat Key Holidays

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