Longboat Key Holidays

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Top Flight + Hotel Deals in Longboat Key

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Providence (PVD) to Tampa (TPA)
8.6/10 Excellent! (2,157 reviews)
Bed comfort , great location, friendly staff.

Reviewed on 6 Aug 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Providence (PVD) to Sarasota (SRQ)
9/10 Wonderful! (1,122 reviews)
Everything was perfect with our stay. We will be back soon.

Reviewed on 4 Aug 2025

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Providence (PVD) to Sarasota (SRQ)
9.6/10 Exceptional! (548 reviews)
I come here year after year and it never disappoints!

Reviewed on 8 Aug 2025

The Capri at Siesta

The Capri at Siesta

3 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Providence (PVD) to Sarasota (SRQ)
9.6/10 Exceptional! (669 reviews)
Clean, comfortable accommodations and so conveniently located. We have stayed here many times and love the staff as well as the location.

Reviewed on 17 Jul 2025

Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Providence (PVD) to Tampa (TPA)
9.2/10 Wonderful! (1,004 reviews)
This was a great place to stay. Wonderful tropical vibe in a relaxed atmosphere. Helpful, friendly staff. Very clean room and many unexpected amenities. Lovely experience.

Reviewed on 10 Aug 2025

Top hotels in Longboat Key

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 €732 per night from 26 Aug to 27 Aug
€732
26 Aug - 27 Aug
includes taxes & fees
9.6/10 Exceptional! (35 reviews)
"Amazing"

Reviewed on 22 Jul 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 €281 per night from 1 Sept to 2 Sept
€281
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"The location was perfect. Centrally located, making trips north and south along the key easy. We were able to quickly go to Sarasota or Ana Maria. The private beach was great. It would have been better without the uncharges for umbrellas and additional lounge chairs. Only 2 lounge chairs per room ..."

Reviewed on 8 Aug 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 €428 per night from 1 Sept to 2 Sept
€428
1 Sept - 2 Sept
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 2 Aug 2025

The Resort at Longboat Key Club
See all 852 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.

What to do in Longboat Key

Picture 1 for Activity Fly Above Water, eFoil Adventure in Sarasota

Fly Above Water, eFoil Adventure in Sarasota

€215
per adult
Fly Above Water, eFoil Adventure in Sarasota
Fly Above The Sea on a Flite Scooter

Fly Above Ocean Adventure on a Flite Scooter!

€216
per adult
Fly Above Ocean Adventure on a Flite Scooter!
Efoil Watersport Experience in Sarsota

Fly Above Water Adventure in Sarasota. A Must Experience!

€215
per adult
Fly Above Water Adventure in Sarasota. A Must Experience!
See all activities in Longboat Key

Frequently asked questions

How much does a Longboat Key holiday package cost?
Offering excellent value package deals from €291 on Expedia, you'll be surprised at how little a holiday 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 holiday 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 holiday for longer.
Is it worth booking a holiday 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 holiday.
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 holiday package well in advance.
Is it cheaper to book a Longboat Key holiday as a package?
You can enjoy significant savings on your next Longboat Key retreat by booking a personalised holiday 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 holiday 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 favourite 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 customised Longboat Key holiday package.

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