Longboat Key Vacation Packages 2025/2026 from $551

Longboat Key flight + hotel vacation packages

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

Hampton Inn Tampa Downtown Channel District

Downtown Tampa

Save 100% on your flight

$551

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features an outdoor pool, a gym, and a restaurant. Enjoy the a rooftop terrace and free perks like full breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a coffee shop are also offered.

Wyndham Grand Clearwater Beach

Save 100% on your flight

$735

per person

Nov 1 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Cedar Cove Resort and Cottages

Save 100% on your flight

$835

per person

Nov 1 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Free WiFi in public areas, a terrace, and a garden are available at this resort. A snack bar/deli, a picnic area, and luggage storage are also on offer.

The Avalon Club

Save 100% on your flight

$607

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

Save 100% on your flight

$781

per person

Dec 11 - Dec 14

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

This aparthotel features an outdoor pool and a 24-hour gym. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Guests will appreciate free perks like valet parking and WiFi in public areas.

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

$714 nightly

$807 total

Sep 22 - Sep 23

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.

On private beach

Pool

Zota Beach Resort

4711 Gulf of Mexico Dr, Longboat Key, FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$270 total

Sep 21 - Sep 22

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

$441 nightly

$498 total

Sep 23 - Sep 24

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.

On private beach

Pool

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.

Pool

Kitchen

THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

$342 nightly

$382 total

Sep 21 - Sep 22

Total with taxes and fees

An outdoor pool is featured at this apartment, along with free WiFi in public areas and a picnic area. Laundry facilities and barbecue grills are also provided.

Pool

Kitchen

Longboat Bay Club

3200 Gulf of Mexico Dr, Longboat Key, FL

Get rates

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.

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.

Popular places to visit

Jewfish Key

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.

Harborside Golf Course at Longboat Key Club

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.

Islandside Golf Course at Longboat Key Club

Enjoy a round of golf in Longboat Key at Islandside Golf Course at Longboat Key Club. Wander the beautiful beaches or discover the area's beautiful sunsets.

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 $551. 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.