Longboat Key Vacation Packages 2025/2026 from $299

Longboat Key flight + hotel vacation packages

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

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

per person

Sep 8 - Sep 12

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Sep 9 - Sep 12

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Twin Palms at Siesta

Save 100% on your flight

per person

Sep 8 - Sep 12

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Sarasota (SRQ)

An outdoor pool, free self parking, and barbecue grills are featured at this hotel. Guests will appreciate perks like free WiFi and a free beach shuttle. A terrace, a garden, and a picnic area are also on offer.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

per person

Sep 14 - Sep 19

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

The Avalon Club

Save 100% on your flight

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

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

$844 nightly

$954 total

Jul 13 - Jul 14

Total includes 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

$285 nightly

$322 total

Aug 3 - Aug 4

Total includes 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

$445 nightly

$503 total

Jul 6 - Jul 7

Total includes 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 CONDO #107. DIRECLY ON GULF FULL VIEW

$389 nightly

$433 total

Jul 8 - Jul 9

Total includes 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

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

$417 nightly

$464 total

Jul 9 - Jul 10

Total includes taxes and fees

A gym is featured at this condo, along with laundry facilities.

Washer

Dryer

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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.

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.

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.

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 $299. 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.