Longboat Key Vacation Homes for Sale

Escape to Elegance on Longboat Key Welcome to this fully renovated, fourth-floor residence at The Promenade, where luxury meets relaxation. This spacious two-bedroom, two-bathroom split floor plan condo boasts breathtaking northwest sunset views.

PENTHOUSE. Delight in scenic views of Sarasota Bay in this custom-designed, rare 4 bedroom, 4.5 bathroom in the gated resort-style Tangerine Bay community on the southernmost tip of Longboat Key. The residence is only minutes from St. Armand's Circle, across the street from the Longboat Key Club, and a short driving distance to the Bay Isles Beach Club and vibrant downtown Sarasota.

BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work.

Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota Bay, white sandy beaches, and the sparkling city skyline. This beautifully designed 2,100 sq. ft. “E” floor plan features three bedrooms and three baths, with a spacious split layout that captures natural light and breathtaking vistas from every room.

Under contract-accepting backup offers. Welcome to this exceptional penthouse residence at Tangerine Bay on Longboat Key. This three-bedroom, three-and-a-half-bath home is one of the largest floor plans in the community and was originally designed and built as the builder’s personal residence, offering features and scale not found in other units.

Your semi-private elevator provides access to the beautiful 7th floor condo with sweeping wide water views of Sarasota Bay and the Gulf of Mexico. At night, the views of the lights of downtown Sarasota and the Ringling Bridge are nothing short of spectacular. Floor to ceiling windows and wrap around terraces provide unparalleled views of the sunrise and sunset over the bay and gulf.

Welcome to this elevated retreat in the sought-after Bayou section of Bay Isles—a seamless blend of sophisticated design and relaxed coastal elegance. Encompassing nearly 2,100 sq. ft. of sunlit interiors, this residence offers an open-concept floor plan with soaring vaulted ceilings, creating an airy, inviting ambiance ideal for both everyday living and effortless entertaining.

One or more photo(s) has been virtually staged. Don’t miss your chance to own a slice of paradise in the highly sought-after Sea Gate Club on historic Longboat Key! Step into unit #7D, where you’ll be captivated by breathtaking, unobstructed views of the Gulf and beach that seem to stretch on forever.

Welcome to Bougain Villa, your Tropical Island Oasis on a deep water canal leading to secluded sandbars, the turquoise waters of the Gulf of Mexico, and several nearby waterfront restaurants. From the moment you arrive at this magical property, Zen Vibes will calm the mind and put it's whimsical spell on you.

Set above the sparkling waters of Sarasota Bay, this beautifully updated 3BR/3.5BA, 2,550 sq. ft. residence in Grand Bay on Longboat Key offers refined living with a seamless, well-planned layout.

Beautifully renovated and offered turnkey furnished, this 3BR/3.5BA residence is perfectly positioned on the 5th floor of Building I in Grand Bay on Longboat Key. A private elevator opens to an elegant, open layout with new wood floors, architectural details, and recessed lighting. Walls of glass frame sweeping views of Sarasota Bay and the Harbourside golf course.

Experience Gulf-front living at its best from this residence perched on a high floor in the coveted Aquarius Club on Longboat Key. This South-facing 2-bedroom, 2-bath split plan offers a bright, open layout with impact-rated floor-to-ceiling windows, doors, and sliders that frame Gulf, beach and tropical views.