Longboat Key Rentals
Compare 11 vacation rentals.
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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.
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Yes, 75 of our Longboat Key homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).
Browse dog-friendly homes >Yes. 245 of our Longboat Key vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Longboat Key team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >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.
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.
