Deals on vacations and trips to Longboat Key

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Longboat Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,033, price is now $618 per person
$618
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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, along with express check-out. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,515, price is now $824 per person
$824
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,299, price is now $744 per person
$744
per person
Oct 20 - Oct 27
found 1 day 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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,583, price is now $1,525 per person
$1,525
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
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.
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 $650 per person
$650
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip 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 self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Top Longboat Key hotels deals

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
$814 nightly
The price is $920 total per night
$920 total
Sep 1 - Sep 2
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
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
$249 nightly
The price is $281 total per night
$281 total
Sep 1 - Sep 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 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
$499 nightly
The price is $564 total per night
$564 total
Sep 1 - Sep 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
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
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key FL
$343 nightly
The price is $383 total per night
$383 total
Sep 1 - Sep 2
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
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Longboat Key FL
Get rates
An outdoor pool is featured at this condo, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
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.

Stay near popular Longboat Key attractions

A lake with clear water, surrounded by dense green trees and a partly cloudy sky.
Photo by throwingsofas
Open Photo by throwingsofas

Jewfish Key

9.0/10 (34 reviews)
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.
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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 $618. 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

A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.
A marina with boats docked, a bridge in the background, and high-rise buildings along the waterfront.
A coastal beach with clear turquoise waters, a long sandy shore, and a backdrop of trees and buildings.
A coastal cityscape with a golf course, residential areas, and a marina.
A beach at sunset with people walking along the shore.

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