Longboat Key Condos For Rent - 73 condos

Remarks: Annual Furnished Rental Available at 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.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)

Remarks: Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous outdoor terrace—ideal for entertaining or simply enjoying the serene waterfront setting. Inside, the chef-inspired kitchen showcases sleek Poggenpohl cabinetry and a full suite of premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, full-size refrigerator, and beverage center. Designed with timeless elegance, the interiors feature curated earth-tone finishes by Marc-Michaels Interior Design. The luxurious owner’s suite offers direct terrace access—perfect for morning coffee with a view—along with a spa-inspired bath complete with dual vanities, soaking tub, oversized glass-enclosed shower, and a Toto bidet water closet. The thoughtfully modified floor plan includes two full bathrooms and comfortably accommodates guests. Set within the exclusive Residences at The St. Regis, this property offers access to over 17 acres of meticulously maintained grounds and 800 feet of pristine Gulf-front shoreline. Residents enjoy an unmatched lifestyle with access to world-class amenities, including personalized butler and concierge services, a renowned spa, in-residence dining, and private resident-only offerings such as a clubhouse, fitness center, pool, spa, and dedicated beach area. Don't miss this rare opportunity to live where others vacation.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)

Remarks: 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 $3950/ month off-season. One tenant must be age 55 or older in accordance with community requirements. Apply now!

Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)

Listing Agent: Geoff Scalera (941-321-4158)

Remarks: LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major updating, with all new designer furniture and furnishings, new custom kitchen and bathrooms. Floor to ceiling glass with panoramic views from every room in the house. MOVE-In and enjoy the Luxury lifestyle and amenities that abound at Grand Bay. GRAND BAY is a 24-hour-manned, GATED community where residents can enjoy two heated swimming pools, hot tub spa, fitness center, tennis, private garage, large clubhouse, many on site activities. Residents can enjoy the Bay Isles Beach Club private beach access to the world famous beach on the Gulf of Mexico. Close to St. Armand's Circle, Downtown Sarasota, and Ana Maria Island. OPEN FOR RESERVATION May through December 2026 for a THREE MONTH or longer stay. There is a 30 day tenant application process with the Grand Bay COA. NO PETS/No Smoking. Additional charges 13% sales/resort tax to be paid by tenants. May through November $7,850. Reservation Confirmed for February through March 2027.

Listing is courtesy of: WAGNER REALTY (941-955-1500)

Listing Agent: Patrice Ivan (941-993-0823)

Remarks: 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!

Listing is courtesy of: ROSSI & COMPANY INC (941-955-7368)

Listing Agent: Deserea Hardy (941-960-6480)

Remarks: AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright and inviting floor plan featuring a well-equipped kitchen, spacious living area, and a private bedroom suite designed for relaxation. The unit includes the added convenience of an in-unit washer and dryer, making extended stays effortless. Enjoy your morning coffee or evening unwind with a Gulf view, while being just moments from the community’s private beach access—only a short walk across Gulf of Mexico Drive. Beach Harbor Club offers resort-style amenities including: Large heated community pool Fitness center Clubhouse for social gatherings Marina and bayfront dock access Community grills and outdoor seating areas Covered parking and bike storage Located in the heart of Longboat Key, you are minutes from Publix, CVS, St. Armands Circle, downtown Sarasota, and Anna Maria Island, giving you easy access to dining, shopping, and entertainment while still enjoying a peaceful beachside setting. Non-smoking unit No pets allowed. Sate and local tourism tax applies to any lease 6 months or less, along with application fees, and $250 cleaning fee.**

Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)

Listing Agent: Brigette Marcus (941-315-9500)

Remarks: ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay. Tastefully decorated with flowing neutral tones. This corner unit offers views from every room with Floor-To-Ceiling windows and remote control window treatments. There are many amenities in this beautifully maintained building. They include Climate Controlled Bicycle Room and Kayak Storage, Gulf Front Heated Pool, Har-Tru Tennis Courts, Fitness Room, Social Room and Conference Room all for your use. Walking distance to Publix Market and minutes to St Armand's Circle and Downtown Sarasota for boutique shopping, Fine and Casual Dining and our renowned Theater District. Don't hesitate to make this your next vacation spot. This property is available beginning 12/04/2025. Building requires a 2 months minimum rental. LUXURY VACATION RENTAL, LONGBOAT KEY, GULF OF MEXICO, SARASOTA VACATION RENTAL.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Teresa Ribaudo (941-376-4500)

Remarks: FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis, pickle ball, and MORE!This condo is on the first floor so it has it's own entry so you don't have to use the elevator. The condo is completely turn key with pool toys and everything. All you need is your toothbrush and a bathing suit! The master bedroom overlooks the center lake and you do have a peek at the ocean. The 2nd bedroom has twin beds and the den has a pull out couch. All of the rooms have tv's. Enjoy coffee or cocktails on the porch for sunrises/sunsets! Utilities, good wifi and basic cable come with the unit. (cap on electric ). Sorry no pets per association. Resort taxes and cleaning fee not included. Come get out of the cold and put your toes in the sands of Longboat Key!! ( sorry porch furniture is in the living room because the balcony is getting painted!)

Listing is courtesy of: STOCKTON REALTY ADVISORS LLC (941-365-2221)

Listing Agent: Annabelle Newland (231-883-7402)

Remarks: Available starting July 15, 2026! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The gathering room opens to the extended kitchen to create continuity in the main living area, perfect for entertaining. Custom imported cabinetry with frosted glass accents, pantry storage, complementary upper and lower cabinetry, solid surface countertops, and a waterfall-edge peninsula with seating for four elevate the space. Premium KitchenAid appliances include a French door refrigerator, dishwasher, double oven, and cooktop. A skylight fills the home with natural light alongside LED, recessed, and drop lighting throughout. Imported marble flooring, porcelain tile, and neutral Berber carpet complete the interior finishes. Both bathrooms have been beautifully modernized with Corinthian Fossil showers, frameless glass doors, floating vanities, and Quartz countertops. The primary en suite features a walk-in closet and sitting area. Multiple sets of sliding glass doors open to the covered balcony, creating the perfect place to enjoy our million dollar sunsets. Residents can unwind seaside along more than 500 feet of shoreline, stroll the lushly landscaped grounds and paver pathways, or enjoy the private community pool and spa. All lease terms shorter than 6 months are subject to 13% tourism tax.

Listing is courtesy of: TNG PROPERTY MANAGEMENT (941-773-9599)

Listing Agent: Scott Nold (941-773-9599)

Remarks: Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and convenience—ideal for both long-term living or a seasonal retreat. Inside, you’ll find soaring high ceilings and a bright, open layout highlighted by a stunning floating staircase and the added convenience of a private elevator, providing effortless access to every level of the home. All-new furnishings and thoughtfully selected artwork create a refined yet relaxed island feel throughout. Designed for both comfort and entertaining, the home features four TVs—including one on the screened patio—WiFi included, and a fully equipped kitchen complete with a wine refrigerator, Nespresso and Keurig machines, and everything needed from cookware to linens for a seamless, turnkey experience. The spacious primary suite offers a true spa-like retreat with a large custom bathroom, double vanities, and a separate walk-in shower. An attached garage adds everyday convenience, while the thoughtful layout ensures both comfort and functionality. Outdoor living is where this home truly stands out. Enjoy a large screened deck with sweeping views of Hole 4 and a tranquil water backdrop, creating the perfect setting for morning coffee, outdoor dining, or relaxing evenings. A dedicated BBQ deck just off the kitchen makes entertaining effortless, while just steps away you’ll find a heated pool and large hot tub, offering a true resort-style extension of your living space. One of the most sought-after features of this home is exclusive access to the private Bay Isles Beach Club. This gated, resident-only beachfront retreat offers a rare level of privacy and comfort on Longboat Key. Enjoy pristine Gulf-front beaches, convenient parking, shaded picnic areas, pavilions, and a relaxed, uncrowded atmosphere that feels worlds away from public beach access. Whether you're enjoying a full day at the beach or catching sunset over the Gulf, this private club experience truly sets the property apart. Located behind the 24/7 manned gates of Bay Isles, this home also places you close to everything you need—Publix, dining, EMS services, and miles of scenic walking and biking paths near the golf course and harbor. Just minutes away, you’ll find the vibrant energy of St. Armands Circle, the luxury of the St. Regis, and the laid-back charm of Anna Maria Island. Available as a 12-month rental or seasonal lease with a minimum 3-month stay, this is a rare opportunity to enjoy turnkey island living with true resort-style amenities in one of Longboat Key’s most desirable communities.

Listing is courtesy of: SECURE DOOR PROPERTY MANAGEMENT (941-231-4065)

Listing Agent: Andrew Clark (941-929-4223)

Remarks: Booked Dec 1st 2026-March 31st 2027. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. 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.

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: Available January - April 15 Call for rates and availability. Prefer three month lease. Tremendous view of the Gulf from this Gulfside/Beachside 2 BR/2 B condo. Direct Gulf front unit. Breathtaking view of the pristine waters of the Gulf of Mexico. Sit on the balcony to your 7th floor unit. Take in the sunsets with your loved ones and friends. Just a couple minutes and you'll be walking on the fine sandy beach. Go for a swim in the heated pool or the invigorating Gulf waters. Close to St. Armand Circle and Downtown Sarasota. Enjoy the best that Longboat Key offers. Condo application fee required

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)

Remarks: DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale kitchen, and tranquil living area. The primary King suite features an elegant walk-in shower and double vanity, along with a guest closet that will provide everything you need for a peaceful night’s sleep. A spacious queen guest bedroom next to the second bathroom, and a cozy third bedroom designed around a queen bed with a twin bunk perfect for additional guests. This unit in a hard to find 8-unit complex with breathtaking Gulf views, a private beach access located on the North end gives you the best of what the Key has to offer, privacy, amazing restaurants throughout Longboat, relaxing beach walks, unforgettable sunsets, a short stroll to many nearby restaurants and is centrally located; only 8 miles north from the renowned St. Armond’s Circle known for its outstanding restaurants and shopping scene, and 8 miles south of Anna Maria Island, known for its good eats, live music and fun atmosphere. Call for rates and availability.

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)

Remarks: STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium features an open concept floor plan with expansive Living/Dining/Kitchen area. The generous size primary bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a desk. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge with 27 acres of lush mature tropical landscaping. This gulf to bay community offers an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Just minutes to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum. NOW AVAILABLE MAY - DECEMBER 2026 - OFF SEASON RATE APPLY - CALL FOR AVAILABILITY.

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Antonietta Car (813-684-9500)

Remarks: **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach, offering you breathtaking full views of the shimmering turquoise waters, sparkling sand, and those iconic Florida sunsets. This is the perfect opportunity to immerse yourself in the serenity of beachfront living during the best time of year. Imagine waking up each morning to the calming sound of waves and enjoying your morning coffee on the balcony as the sun rises over the Gulf. Step inside and be welcomed by the calm coastal colors and casual elegance that make this condo the ideal beach retreat. The community of Arbomar offers amenities that ensure your stay is as relaxing as possible. Take a dip in the heated community pool, stay active in the fitness room, or gather with friends in the community kitchen and lounge. Additional conveniences include climate-controlled storage lockers, a kayak rack, beach chair storage, and laundry rooms on each floor. With all-new Miami Dade certified high-impact windows, including turtle-tinted beachside windows to protect our local sea turtles, you can enjoy the view and feel secure. This spectacular Penthouse condo emphasizes the exclusivity and appeal of spending winter in a beachfront condo.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Norma Mladineo (941-363-1588)

Remarks: 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) (Booked May through the end of November, 2026 and booked January and February of 2027)

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)

Listing Agent: Stephanie Deshaies (941-780-3229)

Remarks: 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.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: John Schafer, V (954-298-6229)

Remarks: Available for season 2027! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by the heated pool, gather at picnic areas and cabanas with grills, or explore the water with provided kayaks. Residents also enjoy a newly renovated clubhouse with library and card & game room and state-of-the-art fitness center. In addition to that, get crafty at the wood workshop (all tools included). This ground floor condo has room to sleep six with three queen size beds. The kitchen is fully equipped with everything you need to prepare meals. There is ample seating for dining and gathering space. In addition to our renowned beaches, Sarasota and Manatee county boasts a vibrant cultural scene, with live theater, concerts, ballet, opera, galleries, museums, and even a rich history with the circus arts! Escape the winter and come enjoy Florida living on Longboat Key.

Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)

Listing Agent: Maureen Plichta (941-812-5799)

Remarks: Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). Minimum 2 month rental and full months only. 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.

Listing is courtesy of: LINDSAY LEASING LLC (941-404-8878)

Listing Agent: Terri Lindsay (941-404-8878)

Remarks: ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets. NOW AVAILABLE: July through December 2026 - OFF SEASON RATES NOW APPLY. Please contact Agent for availability.

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Antonietta Car (813-684-9500)