Longboat Key Rentals

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Make Longboat Key your next getaway—choose from 8 great vacation rentals

More than 11 miles of glistening white sand await on the shores of Longboat Key, the narrow barrier island that sits between downtown Sarasota and the open Gulf of Mexico. You'll spend tranquil days swimming and fishing, you'll practice your forehand in the endless Florida sun, and you'll find everything from fine dining to blissful relaxation at our Longboat Key vacation rentals.

Explore Longboat Key condo rentals, house rentals, and more


Condo rentals

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House rentals

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Longboat Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Whitney Beach View 332 3D Tour
1 Bed | 2 Bath | Sleeps 2

Whitney Beach View 332 - Longboat Key, FL

From $136
"All Decked Out" on the Key 3D Tour
2 Bed | 3 Bath | Sleeps 7

"All Decked Out" on the Key - Longboat Key, FL

From $282
Key Gulf View 302 3D Tour
2 Bed | 2 Bath | Sleeps 4

Key Gulf View 302 - Longboat Key, FL

From $132
Beach Place Vista 504 3D Tour
2 Bed | 2 Bath | Sleeps 4

Beach Place Vista 504 - Longboat Key, FL

From $327
Treetops 3D Tour
3 Bed | 2 Bath | Sleeps 7

Treetops - Longboat Key, FL

From $151

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Recent Longboat Key vacation rental reviews

Every morning it is a different scene. So unbelievably beautiful! My husband and I loved it.
Mary J. | May 2021
Honestly you will wake up every morning and look at the emerald green water in your backyard and wonder why you got so lucky to stay at this home on LBK. The kitchen has plenty of pans to cook! The master bath/shower is terrific. The king bed is super comfortable as well as the pillows. At the end of this condo is your own beach, which was never too crowded. Come back after a day in the surf and relax in the beautiful pool. A close drive to St. Armand Circle! Anna Maria Island! and downtown Sarasota. What an amazing stay. Thank you!!!!
Mary J. | May 2021
Just absolutely love this house , very spacious. Beautiful pool & private beach right there. We stayed 6 weeks & noticed there was not a grill . Vasca contacted owners & had one delivered & set up when we got there .The house had everything we needed , The only disappointed is that it was already for next .
Pam O. | Mar 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Longboat Key, FL?

Eleven miles long and less than a mile wide, Longboat Key is a barrier island that forms the western boundary of Sarasota Bay in Southwest Florida. The west side of the island is known for its sparkling Gulf beaches and the east for its marinas and mangroves. Longboat Key is also just five miles south of charming Bradenton Beach on the tip of Anna Maria Island, and 13 miles northwest of downtown Sarasota.

Things to do on Longboat Key, FL

Whether you're a beach-goer, an angler, or a snowbird flying south for the winter, you'll find plenty to keep you occupied at our Longboat Key vacation homes.

Use 11 different access points to spend an unforgettable day on the sand, whether you choose the simplicity of Whitney Beach or a low-tide excursion out to Beer Can Island. Keep in mind that sailfish, flounder, redfish, and sheepshead also populate these waters, creating a haven for inshore and offshore anglers.

Schedule a morning match at the Longboat Key Public Tennis Center, which maintains 10 clay courts that are available for reservation. You could also rent a boat at Cannons Marina for the day and spend an afternoon birding near Longboat Pass, still making it home in time to catch a spectacular sunset over the Gulf.

Make yourself at home on the sunny shores of Southwest Florida - book your stay at one of our Longboat Key vacation rentals today.