Longboat Key Vacation Packages 2026 from $444

Longboat Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$444

per person

Sep 17 - Sep 21

found 24 hours ago

Roundtrip flight included

Baltimore (BWI) to Tampa (TPA)

A golf course, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Family-friendly amenities include a children's pool and kid-friendly dining, along with hiking/biking trails. Enjoy the 15 outdoor tennis courts and perks like free WiFi.

BeachTrail Lodging

Save 100% on your flight

$719

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Pittsburgh (PIT) to Tampa (TPA)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace and laundry facilities are also provided.

Cedar Cove Resort and Cottages

Save 100% on your flight

$585

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Wyndham Grand Clearwater Beach

Save 100% on your flight

$695

per person

Aug 21 - Aug 25

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Tampa (TPA)

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$487

per person

Sep 3 - Sep 7

found 4 hours ago

Roundtrip flight included

Baltimore (BWI) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Top Longboat Key hotels deals

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$814 nightly

$920 total

Aug 10 - Aug 11

Total with taxes and fees

This luxury hotel features a private beach, a full-service spa, and 3 restaurants. There's fun for all ages with a lazy river and a children's club, and supervised childcare is an added bonus. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$279 nightly

$315 total

Aug 9 - Aug 10

Total with taxes and fees

A private beach and an outdoor pool are featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.

On private beach

Pool

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$519 nightly

$586 total

Jul 19 - Jul 20

Total with taxes and fees

This smoke-free resort features a private beach, a golf course, and a full-service spa. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a playground, and families will appreciate the onsite laundry facilities.

Sea Club I Beach Resort

4141 Gulf of Mexico Drive Longboat Key FL

Get rates

An outdoor pool, free self parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Breathtaking Beach Front Property Ground Floor Condo

Longboat Key FL

Get rates

This condo features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

The Beach on Longboat Key #227 Resort by RVA

Longboat Key FL

$338 nightly

$377 total

Aug 12 - Aug 13

Total with taxes and fees

This condo features free WiFi in public areas, laundry facilities, and barbecue grills.

Pool

Kitchen

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

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.

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Frequently asked questions

How much are vacation packages to Longboat Key?

Enjoy an unforgettable experience in Longboat Key with a vacation package starting at just $444. Organizing your hotels, flights and tours with Travelocity is so simple. And even better, our great deals will leave you with more savings in your pocket for fun, fun, fun!

Where can I get the best vacation package deals for Longboat Key?

Travelocity will be able to help you lock in an unbeatable Longboat Key package deal. With as many as 400 air carriers and 1,000,000 properties across the globe, we know you'll find the perfect mix.

Why should I book my Longboat Key vacation package via Travelocity?

We've got destinations to suit every type of globetrotter, top-notch service and 24/7 support. And the icing on the cake is we'll match any lower price you discover with our Price Match Guarantee.

Can I save money on my Longboat Key car rental if I book it with hotels and flights?

You certainly can with our Longboat Key vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Combine any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With your own set of wheels, all the main sights around Longboat Key are within your reach.