Longboat Key Vacation Homes for Sale

Under contract-accepting backup offers. Set in the sought-after Longbeach community on the northern end of Longboat Key, this beautifully updated, Turnkey Furnished 2BR/2BA residence blends comfort, elegance and effortless Gulfside living. Poised on the second floor, it enjoys picturesque views over the community’s manicured landscape and out toward the shimmering waters of the Gulf.

BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend.

Attention Investors! This is a rare opportunity to own on the beach on LBK and collect rent. The GROSS INCOME from 1/1/25-10/12/2025 is $62,469. This intimate, unique beachfront resort has only 8 condos and is available for daily, weekly or monthly rentals. All condos are beautifully appointed and smoke free. You will enjoy many relaxing hours on the beach where chairs are provided for you.

Located in the quiet, gated community of Bay Isles on Longboat Key, this beautifully renovated – 2nd-floor residence in Harbour Oaks offers over 2,000 square feet of comfortable, thoughtfully designed living space. The entryway has built-in shelves and cubbies that make it easy to keep jackets, shoes, and bags organized.

This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a small, waterfront, boutique midrise building containing only 9 residences: this is island living at its best! It features two bedrooms and 2 and a half b

Where can you get an exquisite 3 BEDROOM Waterfront Condo on the Coveted South End of Longboat Key under 800,000? Discover the ultimate island lifestyle in this END unit beautifully furnished condo located in the highly sought-after Bay Harbour community with a desired southern exposure.

Under contract-accepting backup offers. Beautifully decorated and renovated, furnished 2 bed 2 bath condo with direct Full Gulf of Mexico views. Breathtaking views from the doorway throughout the kitchen, dining and bedroom. The well-appointed kitchen has an open view of the azure blue waters, a breakfast bar, private washer and dryer.

NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Unit 208 | Corner End Unit • Bay & Harbour Views. Welcome to an exquisite, newly remodeled second-floor corner residence in the highly sought-after Longboat Harbour community.

Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace.

Under contract-accepting backup offers. This Atrium unit in Building Five of Fairway Bay built in 1988 is behind the gates of and walking distance to the Longboat Key Club & Resort Bayside. It is a three/bedroom, two/bathroom turnkey-furnished unit on the second floor but on the third level of the building and has direct Sarasota Bay views from the living area and the primary bedroom suite.

REDUCED PRICE! Are you looking for a RESORT home with spacious rooms, fine finishes, vaulted ceilings and the convenience of a condo community with bay and beach access? Look no further. Luxury and style await in this beautifully updated townhouse, located behind the gates of the exclusive Bay Isles resort. With 1,590 sq. ft.

Nestled in the sought-after Fairway Bay community on Longboat Key, this 2BR, 2BA residence offers the perfect blend of serene bayfront living and luxurious amenities, all behind the exclusive gates of Bay Isles.