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SPANISH MAIN YACHT CLUB CONDO - A4687894 - 914 SPANISH DR S #76, LONGBOAT KEY, FL 34228 Just Added on 04/03/2026 10:49AM
$6,750 | Condo 2 bedrooms, 2.0 bathroom , 1 car carport
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises, with Gulf-side sunsets just a short stroll away. Thoughtfully designed and tastefully furnished, the home offers high-end mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. Residents enjoy access to a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, shuffleboard courts, and wonderful neighbors. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a short drive to Anna Maria Island, this property offers the perfect blend of tranquility and accessibility. Whether you're boating, fishing, or simply relaxing in the bright Florida room, this is a rare opportunity to experience the Longboat Key lifestyle at its finest. Seasonal rental rates are $6,750/ month in-season and $4,450/ month off-season. One tenant must be age 55 or older in accordance with community requirements. Apply now!
This listing is courtesy of: AUM FLORIDA REAL ESTATE LLC
SPANISH MAIN YACHT CLUB CONDO - A4687895 - 730 SPANISH DR S #99, LONGBOAT KEY, FL 34228 Just Added on 04/03/2026 9:36AM
$2,800 | Condo 2 bedrooms, 2.0 bathroom , 1 car carport
Experience the pinnacle of coastal living in this beautifully updated, ground-floor condominium in the highly desirable Spanish Main Yacht Club on Longboat Key. This 2-bed, 2-bath residence offers 1,255 sq. ft. of bright, air-conditioned space featuring elegant engineered hardwood floors, modern stone kitchen countertops, and a welcoming living/dining room combination ideal for entertaining. The thoughtful layout includes built-ins, ceiling fans, and a serene primary suite with a spacious walk-in closet. Life at Spanish Main Yacht Club feels like a year-round vacation. This active 55+ community provides premium amenities including deeded beach access just steps away, a sparkling community pool, shuffleboard courts, and a clubhouse with a library and social rooms. Boating enthusiasts will appreciate the bay and harbor access along with an on-site marina. Practical conveniences include inside laundry, an attached carport, **a personal charging station for your electric car**, and maintenance-free living with grounds care and management included. One small pet (up to 35 lbs) is welcome. Ideally situated just minutes from the upscale dining and shopping of St. Armands Circle and a short drive to Anna Maria Island, this home is perfect for those seeking a tranquil waterfront lifestyle. Whether you're boating, fishing, or relaxing in the Florida room, this property offers a rare opportunity in one of the area’s most desirable locations. Available for annual lease beginning April 1, 2026, at **$2,800 per month**, this unfurnished coastal retreat invites you to embrace the best of Longboat Key living.
SLEEPY LAGOON PARK 2 - TB8491342 - 616 LYONS LN, LONGBOAT KEY, FL 34228 6 Days on yellowkey
$4,800 | Single Family Home 2 bedrooms, 2.5 bathroom
Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a tranquil beach lifestyle. Recently impacted by Hurricane Helene, the home has undergone professional remediation and renovation including kitchen, bathrooms and pool. The living area boasts an open floor plan with a cozy corner wood-burning fireplace that adds a warm touch, creating the perfect setting for snug evenings during the cooler winter months. The kitchen has been completely remodeled and equipped with all new cabinets, quartz countertops and appliances, offering plenty of space for culinary adventures. The master suite includes a cedar walk-in closet, an extra linen closet, and direct access to the pool area. In addition to the 2 bedrooms, there is a bonus room that could be made into a bunk room perfect for the little ones or teenagers to make their own retreat. Lyons Lane is renowned for its tranquility and privacy, with lush mangroves lining the opposite side of the street, creating a natural, peaceful ambiance. This unique setting offers the best of both worlds: a serene retreat just moments away from the pristine beaches, boutique shopping, and fine dining that Longboat Key is famous for.
This listing is courtesy of: ROOST REALTY INC.
TANGERINE BAY CLUB - A4687695 - 360 GULF OF MEXICO DR #312, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$6,500 | Condo 3 bedrooms, 2.5 bathroom, 2 car garage
Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your culinary desires an features; European cabinetry, lavish corian counters, Ge Profile Stainless steel appliances, Gas cooktop including an 18-bottle wine cooler and double oven. The chef's kitchen desk space will help you plan your extravagant meals. It is conveniently located near the breakfast nook and view of your courtyard. The open floor is illuminated by natural direct and indirect sunlight. Catch breathtaking sunrises over Sarasota Bay or relax by the gas fireplace during the winter. Hang out on the patio enjoying your favorite beverage and enjoy the lush exotic view. Mahogany doors through the residence give the condo a splendid feel. Stay cool all summer long with the brand- new Comfort Maker A/C unit that was just installed. Cleanses and refresh in your spa-like remodeled master bathroom with a new vanity, separate sinks, new toilet, new jacuzzi tub, tile quartz counters, and spacious neutral tile shower. Come enjoy the outrageous serenity of a LBK sunset. Maybe you will be lucky enough to witness a Flash of Green or Bioluminescence lights. Tangerine Bay offers resort-style amenities centered around one of the luxurious private pools on all of Longboat Key. The amenities include a cabana, fitness center, library, hot tub, and pool surrounded by tropical landscape. The resort also features tennis courts, pickleball courts, and a clubhouse. Organized social including group happy hours in the Cabana, scheduled group pickleball games, and planned excursions to local cultural happenings. Come hang out at Your Private Beach Access at Bay Isles Beach Club for only $250 per year. The privacy and island feel of Tangerine Bay is highlighted by its Bay front living enjoy the recently renovated boat dock which is a secret fishing spot or slip into your kayak and launch out for some peace and serene calm. Longboat key is one of the top destinations for enthusiasts of golf, tennis, fine dining, world-class fishing, and boating. In addition, Tangerine Bay Club is positioned at the southernmost point of the island , walking distance to Quick Point Nature Preserve located on the New Pass and Sarasota Bay. Come check out all the tropical birds and enjoy a stroll through the nature path. Bring your fishing pole or picnic lunch. Tangerine Bay is located across from the famous Longboat Key Club Golf Course . Come enjoy fine dining in downtown Sarasota, St Armands Cir, or many highly rated island restaurants. Just over the bridge is City Island, Mote Aquarium, Ken Thompson Park, and Sarasota Sailing Squadron marina. The St. Armand's Circle shopping district and Lido Key Beach are just a few minutes drive.
This listing is courtesy of: SUNREAL ESTATE INC
PRIVATEER NORTH - A4687317 - 1050 LONGBOAT CLUB RD #506, LONGBOAT KEY, FL 34228 10 Days on yellowkey
$5,000 | Condo 2 bedrooms, 1.5 bathroom
Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights *Direct Gulf-front setting** with dramatic water and sunset views *Renovated interior** designed for relaxation and peace of mind *Primary suite** with a king-size adjustable bed *Guest bedroom** featuring a twin that converts to a king Resort-Style Amenities - Beachfront **pool & spa** with private beach access - Tennis courts**, fitness center, and sauna - Gated entry and secured building access - Library, grill area, and firepit for gathering and unwinding - Assigned **carport parking** plus guest spaces Experience the best of the **Florida coastal lifestyle**—sun, sand, and serenity wrapped in luxury.
This listing is courtesy of: WAGNER REALTY
LONGBOAT KEY TOWERS - A4686763 - 603 LONGBOAT CLUB RD #204N, LONGBOAT KEY, FL 34228 14 Days on yellowkey
$15,000 | Condo 2 bedrooms, 2.0 bathroom
LONGBOAT KEY CLUB – GULF FRONT LUXURY RENTAL Enter the private, gated community of Longboat Key Club and experience true coastal paradise with breathtaking Gulf-front views. This completely remodeled 2-bedroom, 2-bath condominium showcases elegant, high-end finishes throughout. The bright and open living area features stunning marble flooring and walls, with expansive windows and a large private balcony that perfectly frame the panoramic ocean views. The modern kitchen has been thoughtfully redesigned with a sleek style, offering a large island and seamless flow into the living and dining areas—ideal for entertaining. The dining room also enjoys beautiful water views, creating the perfect backdrop for every meal. The spacious primary suite is a private retreat, while the luxurious primary bathroom makes a bold statement with striking black marble finishes. The second bedroom is generously sized and comfortably accommodates double beds. Residents enjoy resort-style amenities including a heated beachfront pool and spa, a state-of-the-art fitness center, sauna, steam room, and 24-hour security. Available for 3- to 6-month stays.
This listing is courtesy of: RE/MAX ALLIANCE GROUP
SANCTUARY I - A4686482 - 575 SANCTUARY DR #A504, LONGBOAT KEY, FL 34228 17 Days on yellowkey
$10,000 | Condo 3 bedrooms, 3.0 bathroom
Welcome to The Sanctuary on Longboat Key, where beachfront living meets effortless comfort. Available as either a 4-month short-term rental for $25,000/month or a 1-year lease at $10,000/month, this southwest corner penthouse offers a rare opportunity to wake up to sweeping Gulf views and end every day with unforgettable sunset skies. From the moment you step through the double-door foyer, floor-to-ceiling sliding glass doors frame endless turquoise water and natural light that fills the living spaces, creating a bright and inviting coastal retreat. Located on the 5th floor, this beautifully updated Essex corner residence offers over 1,800 square feet of living space with 3 bedrooms and 3 bathrooms. Cherry hardwood floors and crown molding elevate the main living areas while large windows and sliding doors keep the Gulf as the star of the show from nearly every room. The kitchen is both functional and stylish, featuring granite countertops, quality cabinetry, top-of-the-line appliances, and a charming breakfast area overlooking Longboat Key’s famous white sand beaches. The owner’s suite is designed as a private retreat with floor-to-ceiling water views, plush carpeting, and an expansive layout. The ensuite bathroom is thoughtfully designed with a dedicated LED-lit vanity and grooming area, separate from the main dual-sink bathroom space which offers plenty of storage. A large jetted soaking tub and seamless glass walk-in shower with a rainhead fixture complete the spa-like feel, while a spacious walk-in closet with a custom closet system provides excellent organization. The thoughtful floor plan also offers a rare feature for a three-bedroom layout: the third bedroom includes its own ensuite bathroom, providing added privacy for guests or family. Additional features include electric storm shutters, newer windows and doors, and a generous utility room. Step outside to the wraparound terrace where the Gulf serves as your everyday backdrop, making it the perfect place to enjoy morning coffee, coastal breezes, or those unforgettable sunset views. Residents of The Sanctuary enjoy 18 acres of beautifully maintained beachfront grounds along with exceptional resort-style amenities including walking trails, covered grilling areas, a clubhouse with social events, a fitness center, spa, Olympic-size Gulf-front pool with cabanas, a children’s pool, and two lighted Har-Tru tennis courts. The community also features a 24-hour staffed guard gate and on-site management. Ideally located on the south end of Longboat Key, you are just minutes from St. Armands Circle, world-class dining, shopping, downtown Sarasota, and a variety of cultural attractions. A small pet is welcome. If you’re looking for a waterfront rental that combines space, privacy, and the best of the Gulf Coast lifestyle, this penthouse at The Sanctuary delivers it all. Schedule your private showing today.
This listing is courtesy of: COLDWELL BANKER REALTY
SPANISH MAIN YACHT CLUB CONDO - A4683730 - 676 EL CENTRO, LONGBOAT KEY, FL 34228 37 Days on yellowkey
$3,250 | Villa 2 bedrooms, 2.0 bathroom , 1 car carport
Experience the best of island living at this luxurious, completely remodeled Longboat Key villa retreat. Renovated from top to bottom, this stunning 2-bedroom, 2-bath residence blends modern elegance with relaxed coastal charm just steps from the Gulf beach. Inside, you’ll find a bright, open layout with high-end finishes throughout. The home features two luxurious full bathrooms, thoughtfully designed with upscale details and a spa-like feel. The brand-new kitchen is bright and open, complete with all-new cabinetry, countertops, and top-of-the-line appliances perfect for entertaining or enjoying quiet evenings at home. A large bright and open living room that blends the dining area and kitchen into an inviting open space. This home has been updated with major improvements for comfort and peace of mind, including a brand new roof and new central air conditioning system. Every detail has been carefully renovated, and the property can be offered fully furnished with beautiful, brand-new furniture, making it truly move-in ready. Plenty of storage space with an outdoor access utility room and separate locked closet with shelves, plus an entire attic with walk-up stairs. The community features a large inground pool with patio tables and chairs, a huge marina with boat slips and great spots to view the manatees and dolphins that swim by. Located directly across the street from private beach access, you’re just a few steps away from the white sands and turquoise waters of Longboat Key. Enjoy morning walks along the shore, breathtaking sunsets, and the peaceful rhythm of island life all right outside your door. Available immediately for annual or seasonal rental, this exceptional property offers a rare opportunity to enjoy luxurious coastal living in one of Florida’s most desirable beach communities. Age requirement of 50+ to rent Annual Rental: $3250/mo Season Rental: $5500/mo (Dec-Mar)
This listing is courtesy of: SAVVY AVENUE, LLC
- A4677888 - 1591 GULF OF MEXICO DR #619, LONGBOAT KEY, FL 34228 81 Days on yellowkey
$78,000 | Condo 4 bedrooms, 4.5 bathroom
There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the tone for an experience that feels both personal and rare. The layout is thoughtful and fluid. Each of the four bedrooms is ensuite, designed with intention, privacy, and comfort in mind. The residence has been fully personalized with a bespoke interior design, every detail chosen, never duplicated. Water views surround you from every angle, sunrise over the bay, sunsets over the Gulf, framed by floor-to-ceiling windows and expansive wraparound terraces. Outdoor dining flows effortlessly into the living spaces, where a private balcony pool becomes an extension of the view rather than a feature competing with it. Inside, the home offers a generous walk-in closet, a custom hidden wine cellar, automated electric blinds, and a fully integrated surround sound system. The residence is offered fully furnished, with all new furnishings curated to complement the space rather than overwhelm it. Beyond the walls of the home, the lifestyle is unmistakably St. Regis with signature amenities, service, and effortless elegance.
This listing is courtesy of: DOUGLAS ELLIMAN
ST. REGIS - A4676510 - 1591 GULF OF MEXICO DR #410, LONGBOAT KEY, FL 34228 94 Days on yellowkey
$40,000 | Condo 2 bedrooms, 2.5 bathroom
An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and relaxation, featuring a custom bar and beverage refrigerator. The chef’s kitchen is beautifully appointed with Poggenpohl cabinetry and top-of-the-line Wolf and Sub-Zero appliances, including double ovens, a gas cooktop, refrigerator, microwave, and dishwasher. An outdoor Wolf gas grill on the terrace allows for seamless indoor-outdoor dining. The owner’s suite serves as a private coastal retreat, highlighted by floor-to-ceiling glass with breathtaking Gulf views. A morning bar adds convenience, while a custom Closet Envy wardrobe provides generous storage. The spa-inspired bath features dual vanities, two private water closets, a walk-in shower, and a luxurious soaking tub with stone surround. The ensuite guest bedroom, complete with custom built-ins, opens directly to the terrace, offering effortless indoor-outdoor living for guests. Designer finishes throughout, curated by Marc Michaels Interior Design, deliver timeless elegance. Residents enjoy exclusive access to St. Regis Longboat Key’s world-class amenities, including a private clubhouse with fitness center, pool and spa, and the signature St. Regis Butler and Concierge services. Additional resort offerings include an oceanfront spa, beachfront cabanas, multiple dining venues, a lazy river, and a saltwater lagoon featuring tropical fish, stingrays, and resident tortoises. Set on 17 acres of pristine beachfront and just 3.5 miles from the renowned shopping and dining of St. Armands Circle, this residence offers a rare opportunity to experience the iconic St. Regis lifestyle—where luxury, comfort, and legendary service define every stay. Rental rates vary according to month, please call agent for details.
This listing is courtesy of: GULF COAST REALTY & MANAGEMENT
LONGBOAT KEY TOWERS - A4674604 - 601 LONGBOAT CLUB RD #902S, LONGBOAT KEY, FL 34228 114 Days on yellowkey
$9,000 | Condo 2 bedrooms, 2.0 bathroom
Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2027. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course from the bedrooms, while evenings wind down with glowing sunsets over the Gulf from the main living spaces. The primary suite offers walk-in closets and a peaceful retreat, and the open layout creates an effortless flow for entertaining or quiet nights at home. Residents enjoy resort-style amenities including a heated beachfront pool and spa, fitness center, sauna, steam room, and around the clock gated security. Water, cable, Wi Fi, and parking are included, making your stay truly effortless. Located within the Longboat Key Club community, Longboat Key Towers offers a serene beachfront escape while keeping you just minutes from the dining, culture, and lifestyle that make Sarasota so special.
This listing is courtesy of: COMPASS FLORIDA LLC
ST. REGIS - A4671506 - 1581 GULF OF MEXICO DR #307, LONGBOAT KEY, FL 34228 145 Days on yellowkey
$20,000 | Condo 1 bedrooms, 1.5 bathroom
The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully designed interiors featuring soaring ceilings and expansive floor-to-ceiling sliding glass doors that wrap around the living, dining, and kitchen spaces — framing breathtaking sunrise and sunset views. The gourmet kitchen is a chef’s dream, appointed with Wolf and Sub-Zero appliances, including a six-burner gas cooktop, double ovens, and a paneled side-by-side refrigerator and freezer. The elegant owner’s suite offers a private sanctuary with a spacious walk-in closet featuring custom wardrobe cabinetry, a frameless walk-in shower, and a secluded water closet. A private elevator with keyless entry provides direct access from your private two-car garage into your residence for ultimate convenience and privacy. Nestled within 17 acres of pristine beachfront, The Residences are part of Sarasota’s most exclusive resort enclave. Enjoy unparalleled amenities, including access to St. Regis Butler and Concierge services, a residents-only pool and spa, a private clubhouse, a state-of-the-art fitness center, and beachside cabanas. Just steps away, immerse yourself in the world-class offerings of The St. Regis Longboat Key Resort — from the pristine private beach and family-friendly pools to the unique saltwater lagoon wildlife experience, home to resident Aldabra tortoises. Indulge in rejuvenation at the oceanfront spa featuring vitality pools or delight in one of the resort’s vibrant, chef-driven dining destinations. Experience coastal luxury redefined — The Residences at The St. Regis Longboat Key invite you to live where timeless elegance meets the serenity of the sea. Inquire about 6 and 9 month pricing.
PRIVATEER SOUTH - A4666443 - 1000 LONGBOAT CLUB RD #1001, LONGBOAT KEY, FL 34228 189 Days on yellowkey
$10,000 | Condo 2 bedrooms, 2.0 bathroom
Available for 2027 Season. Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each offering a front-row seat to breathtaking sunsets, gentle sea breezes, and the soothing sound of waves meeting the shore. Offered fully furnished, this home is designed for both style and comfort, making it the perfect seasonal escape or extended retreat. The residence features a spacious and thoughtfully designed floor plan that emphasizes relaxation and entertaining. The living and dining spaces flow effortlessly toward the water, creating a serene atmosphere for hosting guests or enjoying quiet evenings by the Gulf. The well-equipped kitchen, comfortable bedrooms, and elegant furnishings reflect a refined coastal aesthetic, allowing you to settle in with ease from the very first day. Life at The Privateer is defined by its unparalleled amenities and direct beachfront setting. Residents enjoy a heated beachfront pool and jacuzzi overlooking the Gulf, a fully equipped fitness center, tennis courts, and beautifully maintained grounds. Outdoor grilling areas, shaded dining spaces, and gathering lounges provide endless opportunities for entertaining or enjoying the company of neighbors. For days spent on the sand, beach chairs and umbrellas are thoughtfully provided, ensuring every day feels like a private resort experience. Located on the southern end of Longboat Key, The Privateer combines the peace and privacy of a gated beachfront community with convenient access to world-class dining, shopping, and cultural attractions in nearby St. Armands Circle and downtown Sarasota. Available seasonally beginning October 15, 2025, with owners open to discussing longer lease terms, this residence is the perfect opportunity to experience the best of Longboat Key living—where luxury, comfort, and the beauty of the Gulf of Mexico meet. 3D walkthrough available!!
This listing is courtesy of: KELLER WILLIAMS ON THE WATER S
LONGBOAT KEY - A4663797 - 825 TARAWITT DR, LONGBOAT KEY, FL 34228 213 Days on yellowkey
$10,000 | Single Family Home 3 bedrooms, 2.5 bathroom
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! Intracoastal waterway 50 yards from the point of the canal. Direct access to Sarasota Bay with no bridges! This meticulously maintained home has three bedrooms, two full baths and one half bath plus a one car garage. Open floor plan with spectacular views of Sarasota Bay. Large master bedroom includes a seating area, tv, a large walk-in-closet and a bath with a double vanity and a large walk-in shower. The kitchen and living room open onto a porch with Bay views. The residence was renovated in 2022 and has a new roof and new windows and doors. Other upgrades include granite countertops and new appliances, updated bathrooms, new flooring, freshly painted interior and exterior plus a hot tub. Deeded beach access is directly across Tarawitt Dr for enjoying the beautiful beach and warm Gulf waters on the shores of Longboat Key. The location is walking distance to Harry's Restaurant, Euphemia Haye, The Lazy Lobster, and biking distance to The Shore or Mar Vista. Plus it's an easy drive to Anna Maria, St. Armands Circle and Sarasota.
This listing is courtesy of: BRISTA REALTY LLC
LONGBOAT SHORES REV - A4655401 - 613 BUTTONWOOD DR, LONGBOAT KEY, FL 34228 267 Days on yellowkey
$17,500 | Single Family Home 3 bedrooms, 2.0 bathroom
Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into the crystal clear deep end. Plenty of new stone pool deck on the offered lounge chairs to bask in the Florida sun. Welcome to peaceful Buttonwood Harbour, composed of 50 homes in one of Longboat Key's oldest and sought-after communities. Situated in the middle of Longboat Key, it is walking distance for most, to Publix, the Shoppes of Bay Isles, Tennis, post office, and CVS. Full of friendly neighbors and a favorite place for nature lovers. Boaters and fisherman will be happy with accessibility to the BHA boat ramp for launching and ability to dock your boat at the house during your stay, even utilize the kayak storage if you decide to rent them. No bridges from Buttonwood Harbour out to Sarasota Bay's open waters. Enjoy the day at Bayfront Park, 1.4 miles from the house. Amenities found at Bayfront Park include a 1,350 square foot indoor Recreation Center, a playground, a basketball court, shuffleboard courts, a multi-purpose open field, 3 dedicated pickleball courts, a tennis court, picnic tables, restrooms, and parking for a Town public beach access located across the street. The Bayfront Park Recreation Center is a public recreation facility run by the Town of Longboat Key. You will also find a dog park for your fur babies.
This listing is courtesy of: PRECISE REALTY CORP
PROMENADE - A4658115 - 1211 GULF OF MEXICO DR #1005, LONGBOAT KEY, FL 34228 269 Days on yellowkey
$15,000 | Condo 2 bedrooms, 2.5 bathroom
Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a gourmet kitchen featuring quartz countertops, a breakfast bar, custom glass front cabinets, a glass front refrigerator and custom light fixtures. The flooring is luxury vinyl throughout, the main living area has a wet bar, electric fireplace, flat screen TV and lots of comfortable seating. The primary bedroom has a king bed, wall-mounted flat screen TV, built-in vanity and two walk-in closets, and the primary bath has a spacious shower with built-in seating and dual sinks. The guest bedroom and bath can be closed off for privacy and have a queen bed, wall-mounted flat screen TV and gorgeous water views! The Promenade is an upscale community with recently updated amenities, they have two areas to grill, a wonderful pool and spa, fitness, tennis and private beach access. The property is just five minutes to Publix, CVS and St Armands Circle. Booked from November 1, 2026 to May 1, 2027.
This listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
ST. REGIS LONGBOAT KEY - A4644494 - 1591 GULF OF MEXICO DR #313, LONGBOAT KEY, FL 34228 382 Days on yellowkey
$18,000 | Condo 2 bedrooms, 2.5 bathroom
2027 Season Rental Rate will be $24,000. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero appliances, a six-burner gas cooktop, double ovens, and a panel-ready side-by-side refrigerator/freezer. The owner's suite includes a spacious walk-in closet with custom cabinetry, a frameless walk-in shower, and a private water closet. A semi-private elevator with keyless entry provides direct access from the private garage. Residents enjoy access to The St. Regis Resort's legendary Butler and Concierge services, a private clubhouse, resident-only pool and spa, a state-of-the-art fitness center, and beachside cabanas. Just steps away, the resort offers a private Gulf-front beach, multiple pools with cabanas, a family-friendly waterway, an exclusive saltwater lagoon with Aldabra tortoises, and a world-class oceanfront spa. Experience the pinnacle of coastal elegance at The Residences at The St. Regis Longboat Key.
This listing is courtesy of: MICHAEL SAUNDERS & COMPANY
ST REGIS LONGBOAT KEY - A4642934 - 1581 GULF OF MEXICO DR #507, LONGBOAT KEY, FL 34228 395 Days on yellowkey
$30,000 Reduced | Condo 1 bedrooms, 1.5 bathroom, 2 car garage
Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a modern, chic design, featuring plush seating, rich textures, and sophisticated décor. The gourmet kitchen is fully equipped with top-of-the-line stone countertops, custom cabinetry, and state-of-the-art appliances. The elegant bedroom includes a king-sized bed with luxurious linens, soft lighting, and unique, custom-made furniture. 2 modern bathrooms- one half bathroom for guests and a full bathroom off of the master bedroom that includes high-end finishes, a freestanding soaking tub, a spacious walk-in shower, double vanities, and a calming color palette. The unit also offers a sound system, parking in the private garage and full laundry room. The Resort has plenty of amenities for everyone to enjoy. Enjoy first class dining, an underwater sea lagoon or a lazy river float after drinks at the Monkey Bar. The Resort also offers a spa, coffee shops, butler service, event planning, fitness center, private cabanas and much, much more.
This listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP
TIFFANY PLAZA - A4608766 - 4325 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228 707 Days on yellowkey
$12,000 | Condo 2 bedrooms, 2.0 bathroom
Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel appliances. The dining area offers seating for four, there is a wet bar with beverage chiller for convenience. The living room offers comfortable seating, a flat screen TV and amazing water views! The primary bedroom has a king bed, amazing views, a flat screen TV, and a walk-in closet. The primary bath offers dual sinks and a walk-in shower. The guest bedroom has a King bed and Flat screen TV for streaming. You will love this wonderful location, with shopping and dining close by, and Historic St. Armands Circle is just a short drive away. Welcome to Paradise! (All rates are plus taxes and fees, available February through April 2026
This listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL
TIFFANY PLAZA - A4580185 - 4325 GULF OF MEXICO DR #208, LONGBOAT KEY, FL 34228 956 Days on yellowkey
$5,500 | Condo 2 bedrooms, 2.0 bathroom
Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk in closet and dual sinks and a spacious shower. The second bedroom has a Queen bed, and there is a lovely guest bath. This wonderful end-unit condo has all you need for your perfect vacation! This boutique community offers a sparkling heated pool and private beach, grill area, club room and sauna. All rates are plus taxes and fees. Rates vary by month, call for availability. Booked February through end of April 2026, and July 2026. Also booked January through April 2027.
SEA GATE CLUB - A4561428 - 2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228 1133 Days on yellowkey
$11,950 | Condo 2 bedrooms, 2.0 bathroom
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath condominium boasts a stylishly designed interior that is sure to impress. Experience tranquility in the master bedroom, which offers exquisite bedding and a sitting area with a stunning view of the azure waters. The ensuite master bath provides the perfect sanctuary for relaxation. The gourmet kitchen with stainless steel appliances is perfect for entertaining and the light and bright living room features exquisite seating and state-of-the-art digital components, including a 75-inch TV and DVR. Stay connected with dedicated desk space, a washer and dryer, and Wi-Fi. Large-screen smart TVs are also available for your added enjoyment. Take advantage of resort-style amenities including a gulf-side heated pool, har-tru tennis court, updated social room, state-of-the-art fitness area, and storage for kayaks, paddleboards, and bikes. Conveniently located to shopping, dining, St. Armand’s Circle, downtown Sarasota, and the Arts, this vacation rental has everything you need for a truly unforgettable stay. Don't miss out on this opportunity to live the life you've always imagined! Minimum 4 months stay!
This listing is courtesy of: ANMARK REALTY LLC
PORTOBELLO - A4208788 - 3235 GULF OF MEXICO DR #A302, LONGBOAT KEY, FL 34228 2984 Days on yellowkey
Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes and HD Extreme channel lineup, king size Master bed and guest bedroom provides two double beds, in unit washer and dryer for convenience. One assigned parking space and guest parking available for second car. Wi-Fi and cable package are provided. Heated swimming pool, tennis court and boat dock located conveniently across the street on the bayside of the complex. Only 1/2 mile to Publix shopping and dining center and approximately 5 miles from fabulous St. Armand's Circle. Sorry no pets permitted (no exceptions). No smoking permitted. 13% sales and tourism taxes apply for any rental less than 6 months. Property is available Apr 2025-Dec 2026 and Apr 2027 and after.
This listing is courtesy of: LINDSAY LEASING LLC
SUNSET BEACH - A4194846 - 2109 GULF OF MEXICO DR #1402, LONGBOAT KEY, FL 34228 3145 Days on yellowkey
$8,000 | Condo 2 bedrooms, 2.0 bathroom
LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. This property is available for January & February 2027. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.
This listing is courtesy of: Jennette Properties Inc
LONGBOAT ARMS - A4683575 - 3330 GULF OF MEXICO DR #104D, LONGBOAT KEY, FL 34228
$4,000 | Condo 2 bedrooms, 2.0 bathroom
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.
LONGBEACH ON LONGBOAT KEY - A4679347 - 730 FOX ST, LONGBOAT KEY, FL 34228
$6,500 | Single Family Home 3 bedrooms, 3.0 bathroom
Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room with dining are and spacious kitchen will make you feel at home right away. The kitchen is fully equipped for your convenience. Outdoors of this home is even more welcoming and paradise-life. Lush and tropical garden around the beautiful swimming pool, cabana with comfortable seating or other seating areas are there just for our guests. There is plentiful parking spaces in front of the house or next to it. And - the beaches..yes that is what matters. Whitney Beach on Longboat Key, couple minutes of walk. Or you can visit the Beer Can Island, popular place for boats to hang out. Coquina Beach on Anna Maria Island is not far also. La Paloma just has it all! Sweet home with good vibe close to all you need on vacation!
This listing is courtesy of: ENVISION REALTY PARTNERS LLC
PIERRE - A4431350 - 455 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$10,000 | Condo 3 bedrooms, 3.5 bathroom
Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the sparkling blue waters of the Gulf of Mexico from rear balcony with access from master bedroom and living room. Master bedroom includes king size bed, walk in shower, & dual sinks. Guest bedroom with two twin beds & a King Bed in the 3rd bedroom. Kitchen includes stainless steel appliances & granite countertops. Side balcony access is from dining room and kitchen with a golf course view! Enjoy the amenities of this luxury condo resort, which includes a fitness center, a tennis court, private beach access, heated pool/spa, a gazebo with complimentary grills, 24 concierge/security, and within a golf course community. Rent includes water, sewer, basic cable, and internet. Electric will be a shared expense. Call now for more details!
This listing is courtesy of: ROSSI & COMPANY INC
BEACH HARBOR CLUB - A4685515 - 3806 GULF OF MEXICO DR #C211, LONGBOAT KEY, FL 34228
$2,500 | Condo 2 bedrooms, 2.0 bathroom
2 bed, 2 bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with neighbors in the expansive clubhouse, and get your daily work out in the fitness center! This turnkey, corner unit offers gulf views from the living room and primary bedroom. On-site community laundry and covered parking is available for your convenience. Ideally located in the middle of the key, with easy access to Publix, the chic St Armands Circle, Downtown Sarasota, and the charming Anna Maria Island. Your dream residence awaits! Off season price: $2,500 per month, Seasonal price: $5,000 per month.
This listing is courtesy of: FLORIDA GALLERY REAL ESTATE
COUNTRY CLUB SHORES - A4561269 - 500 SCHOONER LN, LONGBOAT KEY, FL 34228
$11,550 | Single Family Home 2 bedrooms, 2.0 bathroom
Booked January, May, October, and Dec 2026 through February 2027, There is 2 week minimum stay required. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for the gourmet chef in you all. Outdoor living could be your everyday enjoyment while sipping wine by your private heated pool and on cool nights curl up at the fire pit. Sit back and relax with many seating areas and full outdoor dining table in this cozy beach themed oasis in Country Club Shores. Quiet sought out neighborhood on south end of Longboat Key with beach access between LBK Club and Beach Place. It is fully equipped with everything you will need to feel at home while enjoying the sights and comforts that Longboat Key has to offer. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.