Longboat Key Vacation Packages 2026 from $500

Longboat Key flight + hotel vacation packages

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

Kompose Boutique Hotel

Save 100% on your flight

$500

per person

May 1 - May 4

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.

Captiva Beach Resort

South Village

Save 100% on your flight

$599

per person

May 3 - May 8

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 condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.

The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

Save 100% on your flight

$755

per person

May 16 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This smoke-free hotel features 3 outdoor pools, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A poolside bar, a 24-hour front desk, and a terrace are also provided.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$912

per person

Apr 10 - Apr 15

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$798

per person

Apr 30 - May 5

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Top Longboat Key hotels deals

Zota Beach Resort

4711 Gulf of Mexico Dr Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$435 nightly

$492 total

Mar 1 - Mar 2

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

$1,584 nightly

$1,790 total

Mar 25 - Mar 26

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.

The Resort at Longboat Key Club

220 Sands Point Road Longboat Key FL

Free Cancellation

Reserve now, pay when you stay

$929 nightly

$1,050 total

Mar 1 - Mar 2

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

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

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

Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

Longboat Key FL

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An outdoor pool is featured at this condo, along with laundry facilities and barbecue grills.

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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

4/5(6 reviews)

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 $500. 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.