Longboat Key Vacation Homes for Sale

Looking for a beachfront home on Longboat Key with direct Gulf access? This 2-bedroom, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach.

Under contract-accepting backup offers. Discover the charm of Whitney Beach Condominiums, a beloved Gulf-front community on beautiful Longboat Key. This delightful upper floor, end-unit, 2-bedroom, 2-bathroom condominium offers unobstructed views of the Gulf of Mexico and the perfect blend of comfort, character, and coastal charm.

Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year-round or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay.

Welcome to Paradise Found at Harbour Villa Club, a waterfront luxury condo that is truly a slice of heaven on earth. This stunning property offers breathtaking views of the glistening water and is situated in a prime location that is peaceful, serene, and truly one-of-a-kind. A true Longboat Key gem.

Welcome to 2323 Harbour Oaks Drive, a light-filled villa with a wide-open layout and peaceful vistas overlooking the Longboat Key Club golf course and a serene pond. Positioned to capture gorgeous natural light throughout the day, this residence lives effortlessly with soaring ceilings, generous room sizes, and seamless indoor–outdoor connection.

Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club.

Welcome to your dream beachfront retreat at The Promenade. This sunny, south-facing seventh-floor residence offers an open, spacious interior encompassing 1585 sq. ft. of living space. It’s waiting for you to make it your own and embrace the captivating views of the Gulf, Sarasota Bay, and downtown Sarasota from its wraparound terrace.

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This 2 Bedroom, 2 Bath condo overlooking the Gulf has an open kitchen with breakfast bar. It also has a computer nook with a window overlooking the East terrace. The coveted great room design adds to the casual beachfront living experience. The split plan allows for great personal space.

WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you.

Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance.

Experience elevated coastal living in this beautifully renovated, second-floor beachfront condominium, offering sweeping Gulf views and the tranquility that comes with a higher vantage point. Nestled within the intimate, gated community of Sea Pines on the serene north end of Longboat Key, this end-unit residence effortlessly blends updated sophistication with the soothing rhythm of the sea.

One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key.