The Best Longboat Key, FL Chalets from $634

A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Longboat Key chalets

A balcony with a blue sofa, a lantern, and a pergola with umbrellas.

1. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

Siesta Key Village

$564 nightly

Sep 30 - Oct 1

Total with taxes and fees

A balcony with wicker furniture, a small table, and a potted plant.

2. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

Bobbi M.

$1,353 nightly

Oct 6 - Oct 7

Total with taxes and fees

A table with a bottle and glass, surrounded by wicker chairs, set against a backdrop of tall green plants.

3. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

View all properties

Find vacation rentals that suit your style

Private vacation homes

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Island Time: Open Next Week!

10/10 Excellent

"If you are looking for a great experience at Longboat Key. This is it. Heidi, the host was great. She was easy and quick to respond to any and all questions. She even sent cake for my birthday (Thanks again). The condo location is outstanding, right on the beach and our view was phenomenal. We had the best sunsets each night. The condo was well maintained and equipped with all your basic needs. Would highly recommend and hope to stay again."

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

10/10 Excellent

"After an anniversary trip last year and then again in May with our family, my husband and I returned again for our Anniversary! Everything was superb, especially the water pressure from the shower head!! That felt so good after our 14 hour drive!! Right on the beach and not too crowded! Our kids were jealous they couldn’t come back this time. We can’t wait to come back again with the family!"

End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,

10/10 Excellent

"It was the best experience we have had with a vacation rental! The host was incredibly helpful and responsive. The penthouse was immaculate and the view was perfect. We will rent again and I am so grateful for this vacation!"

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent

"This beachfront condo is wonderful! The kitchen was well equipped, the unit very clean and very comfortable. The host was very responsive and easy to work with. Longboat Key is a beautiful area and we loved the location of this unit-quiet beach with an amazing view! I will book again, and highly recommend!"

End of summer sale Take a peek awesome reviews 50 feet from sand

10/10 Excellent

"What a view! It was just breathtaking! Jim is wonderful to work with and communicates very efficiently and promptly. We arrived a little early, and I checked to see if the condo would possibly be cleaned and ready. Since it was we were we were able to check right in. Big thank you for that! We would definitely stay here again!"

Oceanfront Oasis – Longboat Key 226 by RVA

8/10 Good

"Great location and enough space for a couple and kids. I was on a studio with a king bed and a sofa bed. Kitchen had enough stuff. Bathroom doesn’t have shampoo and conditioner. It was ok but i didn’t take mine so i had to go buy it. Publix is very close so that’s also very convenient"

Find out more about Longboat Key

Longboat Key Chalets information

Number of reviews	2
Accommodation	0 Chalets
Lowest Price	$634
Highest Price	$1,519

Explore a world of travel with Expedia

Things to do in Bradenton

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Longboat Key chalets

1. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

2. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

3. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Find vacation rentals that suit your style

Top Longboat Key Hotel Reviews

Island Time: Open Next Week!

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

Step from the Beach.Renovated ground Floor unit 63

The Resort at Longboat Key Club

End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

End of summer sale Take a peek awesome reviews 50 feet from sand

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

Oceanfront Oasis – Longboat Key 226 by RVA

Find out more about Longboat Key

Longboat Key Chalets information

Explore a world of travel with Expedia