Longboat Key Rentals

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Make Longboat Key your next getaway—choose from 9 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, townhouses, and more


Condo rentals

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House rentals

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View 1 Townhouses

Longboat Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Villas of Avignon 105
3 Bedroom | 3 Bath | Sleeps 10

Villas of Avignon 105 - Longboat Key, FL

From $130
Whitney Beach View 332 3D Tour
1 Bedroom | 2 Bath | Sleeps 2

Whitney Beach View 332 - Longboat Key, FL

From $124
"All Decked Out" on the Key 3D Tour
2 Bedroom | 3 Bath | Sleeps 7

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

From $318
Key Gulf View 302 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Key Gulf View 302 - Longboat Key, FL

From $114
Gulfside Stroll on Longboat Key 3D Tour
3 Bedroom | 3 Bath | Sleeps 8

Gulfside Stroll on Longboat Key - Longboat Key, FL

From $275

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Recent Longboat Key vacation rental reviews

The house and the location were great! Vacasa’s local staff was friendly and efficient.
Pavel Z. | Jul 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
Great location right on the Gulf. Lanai with great views of the Gulf and beach. Nice quiet beach for morning/sunset walks.
Clint C. | 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.