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

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Longboat Key cottages

Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is ฿16,679
฿27,719 total
includes taxes & fees
11 Aug - 12 Aug
Siesta Heron 6 / Sunset
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is ฿11,186
฿22,856 total
includes taxes & fees
5 Aug - 6 Aug
Unwind Poolside + Walk to Beach! Sarasota Retreat
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
The price is ฿25,362
฿34,287 total
includes taxes & fees
15 Aug - 16 Aug
Beach Road
House (3 Bedrooms) | Front of property

Pool, Dock & Kayaks: Waterfront Palmetto Home

Pool, Dock & Kayaks: Waterfront Palmetto Home
3.0 star property
Palmetto
10.0 out of 10, Exceptional, (1 review)
"This house was absolutely stunning. The kitchen is fully loaded with double appliances. The pool is warm, clean, and salt water! The view is stunning. The area is safe and quiet. We walked 20 min to hit up a cute coffee shop, paddled the kayaks, and took Uber to the Moat Marine and Planetarium. Great for a family. Better if you have a car. "
United States
Carley
The price is ฿9,171
฿24,293 total
includes taxes & fees
31 Jul - 1 Aug
Pool, Dock & Kayaks: Waterfront Palmetto Home
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.
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Top Longboat Key Hotel Reviews

The Resort at Longboat Key Club

The Resort at Longboat Key Club

10/10 Excellent
"Todo excelente , tanto las instalaciones como el personal de servicio, la playa bastante buena, para el año que viene volvere"
Blanca 3-night trip
Posted 21 hours ago
The Resort at Longboat Key Club
Sea Club I Beach Resort

Sea Club I Beach Resort

10/10 Excellent
"Todo magnífico. Lugar espectacular y la anfitriona no pudo ser mejor. Repetire en otra oportunidad."
Pablo 3-night trip
Posted 11 days ago
Sea Club I Beach Resort

Find out more about Longboat Key

Longboat Key Cottages information

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Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Put your feet up at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and WiFi. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a guest favourite. After checking in and chilling in your comfortable new digs, it's time to head out and start exploring. Coquina Beach and Cortez Beach are among the best family-friendly attractions in Longboat Key.
Why book your cottage in Longboat Key with Expedia?
Booking a cottage in Longboat Key is as easy as deciding on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From high-end retreats to affordable properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveller tastes. As for the best deals around? We've got them too!
How can I find cheap cottages in Longboat Key?
Expedia is here to help you track down cheap cottages in Longboat Key. To find a fantastic stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.