Longboat Key Vacation Homes for Sale

Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views.

Whether you choose resort style living or just want to enjoy vacationing at the beach while earning income when you are not using your condo then this is the place for you! This unit is consistently booked and 2026 is already filling up fast! The entrance to this unit is via beautiful pergolas and lush landscaping, which immediately sets the vibe for a tropical getaway.

Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis is A Perfect Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space, this condo combines comfort, convenience, and a balcony help you unwind and enjoy the fresh coastal air.

Step back in time and experience the “Old Florida Lifestyle” in the heart of Longboat Key’s historic Longbeach Village! Tucked away on the northernmost end of the island, this rare property features two charming Key West–style beach cottages on one lot, surrounded by lush tropical landscaping for a truly private island retreat.

Experience true Bay-to-Gulf living with exclusive access to Sarasota Bay and the Gulf of Mexico through the private gated beach club just steps away! This beautifully fully renovated 2-bedroom, 2-bathroom top-floor end-unit condo in the highly desirable Longboat Harbour community combines modern updates, comfortable living spaces, and stunning water views from almost every room.

Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access.

Top 11 things that make this property special...1) Dog Lovers wait for years for this community..

Modern Waterfront Living in the Heart of Longboat Key-Experience the best of coastal living in this beautifully renovated 2-bedroom, 2-bathroom condo, perfectly situated on the water in one of Longboat Key’s most desirable communities.

Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar.

Exceptional full Bay views, private beach access and kayak launch and incredible value! This fully furnished 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping.

A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seaplace with no shared walls, offering unparalleled privacy and tranquility. Fully remodeled in 2019, the home features a designer kitchen with quartz countertops, custom cabinetry and premium appliances, seamlessly complemented by elegant soft grey laminate hardwood flooring throughout.

Luxury Coastal Living at Longboat Harbour: Experience stunning canal views and modern elegance in this impeccably renovated 3rd-floor condo, ideally situated in the desirable all-age community of Longboat Harbour. Offered turnkey furnished, this beautifully curated residence is ready for your immediate enjoyment, whether you're seeking a winter retreat or full-time coastal living.