Longboat Key Vacation Packages 2026 from $244

Longboat Key flight + hotel vacation packages

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

Lemon Bay Motel

Englewood Central

Save 100% on your flight

$244

per person

Mar 23 - Mar 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Cedar Cove Resort and Cottages

$1,999

per person

Apr 25 - May 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$2,094

per person

Apr 23 - Apr 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free hotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$542

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

Kompose Boutique Hotel

$674

per person

Apr 25 - May 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Top Longboat Key hotels deals

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$395 nightly

$446 total

Feb 4 - Feb 5

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 St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL

$1,344 nightly

$1,519 total

Feb 4 - Feb 5

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

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$749 nightly

$846 total

Feb 9 - Feb 10

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.

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.

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

Country Club Long Boat Key Beach Villa 2B 3BA Pool

Longboat Key FL

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This vacation home features a water park, a garden, and laundry facilities.

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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.

The Cannon near St. Thomas Island Marina

Cannons Marina

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

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.

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 $244. 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.