Longboat Key Vacations from ₩350,332

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The Latest Longboat Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

2 out of 5
Terrace Park
per person
Oct 27 - Oct 29
found 15 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8.4/10 Very Good! (1,289 reviews)
Stayed for the weekend while visiting Busch Gardens. Hot breakfast. Clean, convenient & reasonably priced. Would definitely stay here again.

Reviewed on Aug 1, 2025

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

2.5 out of 5
per person
Oct 27 - Oct 29
found 15 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
9.4/10 Exceptional! (1,015 reviews)
My stay was excellent. The room was comfortable and clean, friendly hotel staff.

Reviewed on Aug 4, 2025

Hotel Haya

Hotel Haya

4 out of 5
Ybor City
per person
Oct 27 - Oct 29
found 15 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
9.2/10 Wonderful! (1,602 reviews)
This is a beautiful property located in a great area. It is half a block from a free trolly that runs every fifteen minutes and will take you all the way into town (11 stops total). The staff are excellent. I only deducted one start because our room, while cool enough, was quite humid.

Reviewed on Aug 4, 2025

Aloft Tampa Midtown

Aloft Tampa Midtown

3 out of 5
Midtown Tampa
per person
Oct 27 - Oct 29
found 15 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8/10 Very Good! (458 reviews)
Got it mixed up with the one Downtown but glad it turned into a running joke with the receptionist. So fun and different from hotels I’m accustomed too. Its in a great location 10/10 highly recommend. Very clean, all the staff were friendly and helped me out with any problems. A lot of great places surrounding it!

Reviewed on Jul 30, 2025

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Rocky Point
per person
Oct 27 - Oct 29
found 15 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8.4/10 Very Good! (1,001 reviews)
Check in was not a great experience. The receptionist was rude and not very informative. Our grievances were handled at check-out with a different receptionist and the manager. They were very apologetic. The toilet in our room had a broken handle. Overall, the hotel was great. Comfortable bed. Nice water pressure. Bellhop service was great. There’s a Starbucks inside of the hotel and it’s close to other convenient locations.

Reviewed on Aug 4, 2025

Find the Best Longboat Key Vacation Packages

Longboat Key Hotel 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
Fully refundableReserve now, pay when you stay
The price is ₩968,094 per night from Aug 19 to Aug 20
₩968,094
₩1,180,021 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (34 reviews)
"Amazing"

Reviewed on Jul 22, 2025

The St. Regis Longboat Key Resort
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is ₩344,858 per night from Sep 1 to Sep 2
₩344,858
₩452,290 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Beautiful hotel very good services bed comfort"

Reviewed on Aug 3, 2025

Zota Beach Resort
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is ₩555,373 per night from Sep 1 to Sep 2
₩555,373
₩690,172 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (661 reviews)
Great exclusive place
"At $500 / night the place had better be 5* and more !! Service was great !!"

Reviewed on Aug 2, 2025

The Resort at Longboat Key Club
See all 849 properties in Longboat Key
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.

Frequently asked questions

How much does a Longboat Key vacation package cost?
Offering excellent value package deals from ₩350,332 on Expedia, you'll be surprised at how little a vacation to Longboat Key costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Longboat Key?
January, August and December are the best times to search for cheap Longboat Key vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Longboat Key?
With a well-planned itinerary, you can easily hit the top Longboat Key attractions in a few days. But if you'd like to discover hidden gems or take day trips, consider booking your Longboat Key vacation for longer.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has everything you need for a fantastic trip — coastal beaches, views and watersports are just the start. Whether you'd like to check out attractions such as Jewfish Key and Cannons Marina, or venture off the beaten track, there's plenty to experience on your Longboat Key vacation.
How to find the best Longboat Key package deals?
Use Expedia's handy filters to help you find some tempting Longboat Key package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Longboat Key package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Longboat Key vacation as a package?
You can enjoy significant savings on your next Longboat Key retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Longboat Key?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Longboat Key trip.
How to plan a trip to Longboat Key?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favorite season and the available activities will also help you decide when to visit Longboat Key.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Longboat Key.
  3. Decide how many days away: Start by listing all the activities and attractions you want to get to in Longboat Key. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Longboat Key vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.