Longboat Key Vacation Homes for Sale

Welcome to the Islander Club situated directly on an amazing stretch of beach in fabulous Longboat Key! This meticulously kept 2 bedroom, 2 bath residence features an updated kitchen and baths, beautiful flooring throughout, and not one but two balconies, one off the living room overlooking the lush grounds and another very large balcony that has a view of the sparkling Gulf of Mexico! Enjoy peace

Ideal for area residents needing space for overflow guests, or for out-of-state owners who want unlimited use with the ability to still earn income! The most perfectly peaceful lagoon views are enjoyed from this first floor Junior Suite in Building 6. Unlike the other buildings, this building boasts 10' ceilings making it feel especially spacious while optimizing natural light and view.

Income-Producing Coastal Gem – This TURNKEY FURNISHED 2BR/2.5BA townhome in the exclusive Cedars East Tennis Resort isn’t just a slice of paradise—it’s a proven performer. With $80,000 in past annual rental income and future bookings already secured, this property offers immediate cash flow and long-term upside.

This property s a STEAL! Motivated seller has reduced this waterfront property far below any other property on Longboat Key. Don't miss the opportunity to build your dream home in this established neighborhood nestled next to Joan M. Durant Bayfront Park and beach access across the street.

Under contract-accepting backup offers. Welcome to coastal living! This beautifully renovated, fully furnished 2BD/2BA end-unit condo on Longboat Key, offering stunning bay views and bright, beachy vibes throughout. This home is being sold fully furnished, making it effortless to settle in and start enjoying the island lifestyle right away.

Discover the ideal blend of comfort, convenience and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key.

104 ft. x 29.5 ft. Boat Slip at Longboat Key Moorings Marina. This is a 104 ft. long T-dock/face dock ready to accommodate a large yacht; ample electrical service outlets. O-13 is 49.5 feet, and O-14 is 54.5 ft, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay.

This inviting residence at the Islander Club of Longboat Key offers a peaceful retreat with beautiful views of the landscaped grounds. Spanning 1,235 sq ft, the home features two bedrooms, two full bathrooms, and an open floor plan that provides a comfortable space for both living and entertaining.

Offered at $599,000! This stunning residence presents an incredible opportunity to experience the coveted Longboat Key lifestyle. Welcome to your completely renovated coastal retreat, bright, airy, and beautifully designed to capture breathtaking water views of Crane’s Bayou, Buttonwood Harbor, and Sarasota Bay.

Under contract-accepting backup offers.

BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed March 26, 2025 for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor plan boasting recessed lighting and an array of sleek finishes throughout the home.

This beauty is ready for a new owner! Enjoy island living nestled in the VIBRANT community of Longboat Harbour on beautiful Longboat Key.