Deals on vacations and trips to Longboat Key

Save when you book Longboat Key package deals

Choose two or more items and save on your trip:

Longboat Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $655, price is now $415 per person
$415
per person
Apr 16 - Apr 20
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Save 100% on your flight
Price was $3,410, price is now $2,029 per person
$2,029
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,984, price is now $1,821 per person
$1,821
per person
Apr 20 - Apr 24
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.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,030, price is now $658 per person
$658
per person
May 2 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $859, price is now $578 per person
$578
per person
Apr 11 - Apr 14
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.

Top Longboat Key hotels deals

Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
$439 nightly
The price is $496 total per night
$496 total
Feb 16 - Feb 17
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

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive Longboat Key FL
$1,674 nightly
The price is $1,892 total per night
$1,892 total
Feb 16 - Feb 17
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

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
$929 nightly
The price is $1,050 total per night
$1,050 total
Feb 22 - Feb 23
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

Longboat Bay Club

3.5 out of 5
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

Sea Club I Beach Resort

3 out of 5
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 bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

Longboat Key FL
Get rates
An outdoor pool is featured at this condo, along with laundry facilities and barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Longboat Key
View all properties
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 is a private island that we kayaked around. We saw a couple dolphins playing nearby too, but the main attraction to the public is large sandbar nearby. We rented our kayaks from a place called Kayak Jack's. They were great! You pick a drop-off location and specify a time and your kayaks will be awaiting you, ready for launch! http://www.kayak-jacks.com “You choose the location, We bring the Fun!”

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.

Jewfish Key
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.

Cannons Marina
Wildlife reserve

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.

Quick Point Nature Reserve

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 $415. 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.

Photos of local treasures

Browse Longboat Key vacation photos for more inspiration

1_140312352
1_140312352
Jewfish Key is a private island that we kayaked around. We saw a couple dolphins playing nearby too, but the main attraction to the public is large sandbar nearby. We rented our kayaks from a place called Kayak Jack's. They were great! You pick a drop-off location and specify a time and your kayaks will be awaiting you, ready for launch! http://www.kayak-jacks.com “You choose the location, We bring the Fun!”
The Mote is such an interesting aquarium and research center. Thank you to my fellow Trovers for posting pics.
Sunset over the beach on Longboat Key.

Explore More Ways to Travel with Travelocity