Longboat Key Vacation Packages 2025/2026 from $366

Longboat Key flight + hotel vacation packages

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

The Retreat at Anna Maria Island Inn

Save 100% on your flight

$366

per person

Nov 16 - Nov 19

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Sarasota (SRQ)

An outdoor pool is featured at this hotel, along with free self parking. Express check-out is also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$2,487

per person

Nov 22 - Nov 29

found 5 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Sarasota (SRQ)

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

The Avalon Club

Save 100% on your flight

$992

per person

Nov 13 - Nov 19

found 1 day ago

Roundtrip non-stop 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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$777

per person

Dec 22 - Dec 28

found 24 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Captiva Beach Resort

South Village

Save 100% on your flight

$978

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

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

Oct 5 - Oct 6

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

$259 nightly

$293 total

Oct 5 - Oct 6

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

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 Resort at Longboat Key Club

220 Sands Point Road, Longboat Key, FL

Free Cancellation

Reserve now, pay when you stay

$429 nightly

$485 total

Oct 26 - Oct 27

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

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

$387 nightly

$431 total

Oct 12 - Oct 13

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 $366. 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.