Longboat Key Rentals

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USA > Florida > Longboat Key

Make Longboat Key your next getaway—choose from 14 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

View 8 Condo rentals

House rentals

View 5 House rentals


View 1 Townhouses

Longboat Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Gulfside Stroll on Longboat Key 3D Tour
3 Bedroom | 3 Bath | Sleeps 8

Gulfside Stroll on Longboat Key - Longboat Key, FL

From $275
Beach View Bliss 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Beach View Bliss - Longboat Key, FL

From $153
Beach Place Vista 504 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Beach Place Vista 504 - Longboat Key, FL

From $258
Key Gulf View 302 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Key Gulf View 302 - Longboat Key, FL

From $107
Starfish Palace 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Starfish Palace - Longboat Key, FL

From $300

View 9 more homes

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
Everything was well communicated in advance - how to access, etc. Place was totally clean when we got there. There are towels for the beach and for bathing. The beach is right out the door, downtown Longboat is about 10 minutes away. Be a little cramped for 4 people but great for 2. This review was submitted while the home was managed by a different property management company.
James D. | Jul 2021
Every morning it is a different scene. So unbelievably beautiful! My husband and I loved it.
Mary J. | May 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.