Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

Christina Vescovo LPT REALTY, LLC

Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances

Christina Vescovo LPT REALTY, LLC

NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL ($4,600/MONTH). LEASE -3 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

Norma Mladineo COLDWELL BANKER REALTY

Charming Cortez Coastal Cottage – Minutes from Anna Maria Island! Located in the sought-after Cortez area in the Sunny Shores Community, just moments from the sugar-sand beaches of Anna Maria Island. Enjoy the charm of Old Florida fishing villages, nearby marinas, fresh seafood dining, and the laid-back island lifestyle—all just minutes from your doorstep. 3BR/2BA unfurnished single family home 8

Stephanie Bell FRAN MAXON REAL ESTATE

Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

Teresa Ribaudo JENNETTE PROPERTIES INC

Lovely home in Perico Isles just minutes from Anna Maria Island and its wonderful beaches. This home has three bedrooms, two baths, two car garage, laundry room and swimming pool. Robinson's Preserve is just beyond the property line and the pool area is very private. First, last and security.

Lisa Varano WAGNER REALTY

Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows

Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle.Key Features:-Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the

Miranda Platt, PA RELAX REALTY GROUP INC

Welcome to your new Beach House Sanctuary!! Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot! Coveted lifestyle and location on a deep water canal in the heart of Longboat Key! This waterfront home has 125ft of seawall docking for a boat up to 30 ft. plus a jet ski lift and room for other water toys. Catch bait and start fishing in less than 30 minutes!

Ian Greenberg BRISTA REALTY LLC

AVAILABLE STARTING MAY 1, 2026. WITH 3 MONTH MINUMUM RENTAL. FULL WATERFRONT NEWLY RENOVATED (internal new photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main Yacht

Norma Mladineo COLDWELL BANKER REALTY

Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room

Rinat Sikdar COLDWELL BANKER REALTY

Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost 2500 Sq. Ft. of Interior Living, The Home Offers 4 Bedrooms, 3 Full Washrooms, 2 Balconies and

Ian Greenberg BRISTA REALTY LLC

Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step

Andy Moore GULF COAST REALTY & MANAGEMENT

Welcome to Mangrove Escape, Professionally managed by Gulf Coast Vacation Rentals, your slice of paradise in the highly sought-after Perico Bay Club! This beautiful 2-bedroom, 2-bathroom waterfront home offers a light and bright coastal vibe paired with stunning views of the mangroves and direct water access just steps from your back door.Perico Bay Club means enjoying a vibrant,

Andy Moore GULF COAST REALTY & MANAGEMENT

Beachside Luxury Rental – 3BR, 2.5BA with PoolLive just steps from the sand at 4808 Gulf Drive Unit B, an upscale and fully furnished 3-bedroom, 2.5-bath home located in the heart of Holmes Beach. Available for starting July 19th, this multi-level coastal retreat blends modern comfort with laid-back island living—perfect for a long vacation or seasonal stay.Step into a bright,

Nataliya Fillers FUTURE HOME REALTY INC

Located Approximately 10 minutes from IMG academy (shuttle to IMG provided), and just a stone's throw away from Bradenton Beach bridge, this turnkey, utility free, fully furnished, brand-new residence is the pinnacle of coastal living that offers both luxury and sustainability located just a short walk on the Cortez bridge from the sun-drenched beaches of Anna Maria Island. This home is an

Liz Andricks MICHAEL SAUNDERS & COMPANY

Welcome to Saltwater Serenity at Hunters Point! *Community is currently under construction*Available for monthly lease starting at $12k/month. For season rates, Dec-April inquire for more info! Utilities included with rent.The perfect location for those who are looking to not only travel to the wonderful sandy beaches of the Gulf Coast but also would like the option to bring a

Benjamin Dietrich ANCHOR DOWN REAL ESTATE

Canal Front, Swimming pool with recently added cage and replaced pool surface, small boat dock where a boat may be secured (Lift not included).This is a three bedroom home and two full bath the third bedroom is part of additional suite including twin beds, sofas, TV plus a private office. An additional toilet is in the laundry room which is situated between the kitchen and

T. Dolly Young T DOLLY YOUNG REAL ESTATE

Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

Jaime Barcelo GULF COAST REALTY & MANAGEMENT

Welcome to Vitamin Sea! This exquisite 3-bedroom, 3-bath private pool home sits at the end of the cul-de-sac overlooking the stunning canal, with mature landscaping all around the home. This home offers the perfect location to it all! You are just 2.5 miles away from the gorgeous white sands of Bradenton Beach and just 2.8 miles from magnificent Bridge Street, where you will find restaurants and

Andy Moore GULF COAST REALTY & MANAGEMENT