Longboat Key Rentals

Compare 9 vacation rentals.
USA > Florida > Longboat Key

Make Longboat Key your next getaway

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 5 Condo rentals

House rentals

View 3 House rentals


View 1 Townhouses

Popular amenities for Longboat Key vacation rentals

Dog-friendly Hot tub Internet
Whitney Beach View 332
1 Bedroom | 2 Bath | Sleeps 2

Whitney Beach View 332 - Longboat Key, FL

$137 avg / night (excludes fees and taxes)
Whitney Beach 149
1 Bedroom | 1 Bath | Sleeps 4

Whitney Beach 149 - Longboat Key, FL

$130 avg / night (excludes fees and taxes)
Beach to Bay View
3 Bedroom | 2 Bath | Sleeps 9

Beach to Bay View - Longboat Key, FL

$301 avg / night (excludes fees and taxes)
Freesia at Seaside Gardens
2 Bedroom | 2 Bath | Sleeps 6

Freesia at Seaside Gardens - Longboat Key, FL

$166 avg / night (excludes fees and taxes)
Gulf Front Paradise
3 Bedroom | 2.5 Bath | Sleeps 6

Gulf Front Paradise - Longboat Key, FL

$317 avg / night (excludes fees and taxes)

View 4 more homes

Recent Longboat Key guest reviews

Easy access to beach; Well maintained, attractive grounds; sunny apartment. Friendly community.
Neal S. | Feb 2024
Charming beach house literally two blocks from the beach. Plenty of room for 6. Great downstairs outdoor shower area to keep all your beach toys and sandy toes washed and separate from living area. Walkable to at least 6 places to eat from diners to high end dining. Dog-friendly neighborhood.
Kristen W. | Jul 2023
Cozy condo in fabulous location
Teresa O. | Mar 2023
Longboat Key vacation rental FAQ

Yes, 111 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. 326 of our Longboat Key vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Longboat Key vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

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 >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Longboat Key, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.