Longboat Key Vacation Homes for Sale

Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key retreat on 26 bayfront acres, with half a mile of walking trails along the Bay. Pre-closing possession possible so you can begin your Longboat Key season on January 1, 2026.

This spacious waterfront villa lives like a single-family home yet offers the ease of maintenance-free living! Enjoy breathtaking Sarasota Bay and canal views from this 1,900 sq. ft. residence—the largest in the community.

Set in the sought-after Longboat Harbour community on Longboat Key, this beautifully updated 2BR/2BA walkout residence offers 1,152+/- sq. ft. of inviting waterfront living. Your breath will be taken away by the peaceful mangrove-lined views that shape a relaxed, effortless way of life.

Turnkey-Furnished Longboat Key Condo with Dock Access & Short-Term Rental Potential Experience the best of coastal living in this beautifully furnished turnkey condo on highly sought-after Longboat Key.

One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Welcome to coastal living at its finest! Located in the highly sought-after BeachPlace III community on Longboat Key, this rarely available sunny 2-bedroom, 2-bath corner condo offers the perfect blend of beachside tranquility and resort-style amenities.

Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures.

Coastal Elegance on Longboat Key – Beachfront Living Redefined! Welcome to an extraordinary beachfront retreat where the serene rhythm of the Gulf meets refined island living. This beautifully appointed two-bedroom, two-bath residence offers beautiful views of the common grounds, entrance and tennis courts.

Gorgeous coastal renovation, waterfront location, deeded beach, pet friendly and more. Enjoy this new, fully renovated two-bedroom, two-bath furnished bayfront condominium in Longboat's Pelican Harbour & Beach Club. Association amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, kayak launch and owner boat docks.

This desirable first-floor corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully refreshed with a neutral color palette and comes fully furnished, and is the lowest-priced unit in Grand Bay.

Under contract-accepting backup offers. Experience breathtaking Sarasota Bay views from every room in this beautifully customized Windward Bay condominium. This coastal retreat offers a seamless blend of elegance and comfort, featuring designer upgrades and thoughtful touches throughout.

Beautiful, custom 2024 renovated second floor two bedroom, two bathroom Pelican Harbour & Beach Club condo with panoramic Sarasota Bay views plus Deeded Beach access right across the street. Stunning water views across Sarasota Bay are yours from the Great Room, the Primary Bedroom & from your waterfront, covered & screened in Balcony.

Under contract-accepting backup offers. Sweeping bay views and refined comfort define this beautifully maintained 2BR/2BA residence in Fairway Bay on Longboat Key. A full wall of floor-to-ceiling sliders in the living room frames stunning views of the mangroves and open water, bringing the beauty of the bay into everyday living.