Longboat Key Vacation Rentals from $325: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Longboat Key has to offer?

Siesta Key Island Rentals : This vacation home rental near Longboat Key comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

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Our top choices for Longboat Key vacation rentals

Sunset and beach view from your balcony Unit 403

Longboat Key

Anonymous traveler

Luxurious Beachfront Jr. Suite by FVC

Longboat Key

Debra J.

$678 nightly

Jun 20 - Jun 21

Total with taxes and fees

Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Longboat Key

Maria

$477 nightly

Jun 20 - Jun 21

Total with taxes and fees

The Beach on Longboat Key #227 Resort by RVA

Longboat Key

Mark H.

$423 nightly

Jul 15 - Jul 16

Total with taxes and fees

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Longboat Key

Rhonda V.

$275 nightly

Jun 21 - Jun 22

Total with taxes and fees

Island Time: Open July 7 - 10!

Longboat Key

Bonnie N.

$438 nightly

Jul 7 - Jul 8

Total with taxes and fees

Cabana Beach Club - Beachfront Stunning Ocean View Snow Bird Promo Winter 2027

Longboat Key

Tracey s.

$590 nightly

Jun 20 - Jun 21

Total with taxes and fees

On the beach, sun loungers, beach towels

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key

Linda D.

$412 nightly

Jun 24 - Jun 25

Total with taxes and fees

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Top Longboat Key Hotel Reviews

Zota Beach Resort

10/10 Excellent

"We had a wonderful stay at Zota Beach Resort and would absolutely recommend it to anyone visiting the area. The staff was outstanding throughout our entire stay—friendly, attentive, and always willing to help. The housekeeping team was especially impressive. They cleaned our room each morning and even made an additional round in the afternoon to check if we needed fresh towels, amenities, or anything else. That level of service really stood out and made our stay even more comfortable. We also loved dining at Viento Restaurant. The food was genuinely delicious from breakfast through dinner. Every meal was fresh, flavorful, and exceeded our expectations. The resort itself is beautiful, well-maintained, and very family-friendly. Traveling with kids can sometimes be challenging, but Zota Beach Resort made it easy and enjoyable for our whole family. Overall, we had a fantastic experience and would definitely stay here again. Highly recommended for families, couples, or anyone looking for a relaxing beach getaway! 🌴☀️🏖️"

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent

"We had a wonderful stay! The condo was perfect for a couple! The grounds were beautiful. I wish there were more laundry facilities and an elevator would be helpful for the handicapped! But otherwise I would recommend and stay again! We had an issue getting into the room but come find out my husband was using an incorrect code… However the owners and the staff were fabulous with helping us to get back into our room!"

Direct Beachfront Gulf with Amazing Views

10/10 Excellent

"We have stayed at Cabana for years, but this was the first time in this condo. I was concerned about the number of stairs but it wasn’t an issue at all. The beds were so comfortable and the kitchen so well stocked! You honestly can’t beat the view from this top floor condo. We love this end of the beach-literally steps away from the ocean."

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

10/10 Excellent

"Beachfront!! View and location is a PERFECT! Love that you have your own patio. Can take the lounge chairs to the beach and bring back. There is an umbrella as well that can be taken to the beach.Saw dolphins in the morning right outside the condo.Lots of wildlife to watch. Ocean is beautiful. Water is clear and beautiful. Non crowded beach. Amazing restaurants nearby.Host very communicative. We will definitely be back!"

Country Club Long Boat Key Beach Villa 2B 3BA Pool

10/10 Excellent

"Absolutely all that we hoped for and more. I didn’t want to leave! This place will be our family go to for years to come. Elicia and Mike are superior hosts and communicators. If anything was not “to their expectation” or was rusty, broke or missing Elicia asked to let them know and it would be replaced. Nothing was wrong at all! It was clean, beautiful and exceeded expectation in every way. So many options for beaches, gorgeous pool, interesting wild life. We saw manatees two days in the gulf. I thank you for everything Elicia and Mike! Can’t wait to return."

Price trends for vacation rentals in Longboat Key

Less expensive	More expensive	Next month
October	February	$458

Month	Price
January	$430
February	$539
March	$484
April	$441
May	$409
June	$463
July	$458
August	$384
September	$374
October	$371
November	$394
December	$429

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Longboat Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Longboat Key

Everything you need to know about Longboat Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Longboat Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Longboat Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Longboat Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Longboat Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $325 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Longboat Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Longboat Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Longboat Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Longboat Key has to offer?

Siesta Key Island Rentals: This vacation home rental near Longboat Key comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Longboat Key?

Choose from 23 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Jewfish Key and Longboat Key Beaches are a couple of lovely local spots to get outside and enjoy nature. Siesta Key Beach and Coquina Beach are other popular places to visit in the area.

What are vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Room 1

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Our top choices for Longboat Key vacation rentals