Remarks: 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 and a gas range. The private, fully fenced backyard offers a lagoon style heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing sound of swaying palms. Completely reimagined 1920 historic bungalow, originally serving as a temporary US Post Office after a hurricane. Serene Village location with no public parking ensures exceptional peace and privacy. Ample boat/RV parking on site and deeded bay access steps away. Walk to Mar Vista Dockside Restaurant & Pub; minutes by car or bicycle to St. Armands Circle and Lido Beach. Offered fully furnished for a minimum 28-day rental period. Two king suites with dual closets each plus queen sleeper sofa in the main house. Ideal snowbird retreat or extended-stay executive residence. There is also a sweet one bedroom apartment above the garage with a queen bed, queen sofa & beautiful balcony overlooking the pool Available now—just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Christina Vescovo (314-743-7111)

Remarks: Available for season 2026 Looking for a 3 month rental. Newly renovated, this beautiful home features a split floor plan with generously sized bedrooms and walk-in closets, all enhanced by a charming coastal flair. The kitchen—truly the heart of the home—is fully equipped with everything you need to prepare delicious home-cooked meals. Enjoy your morning coffee or an evening cocktail in the cozy coffee-bar area. 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.

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

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

Remarks: Booked January, May-June 8th, October, and Dec 2026 through April 15th 2027, May 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.

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

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

Remarks: Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home features four bedrooms, a spacious bonus room, and a dedicated office, providing plenty of space for both relaxation and productivity. The private heated pool and spa create a resort-style retreat in your own backyard, surrounded by lush, meticulously maintained landscaping. Inside, the gourmet kitchen boasts modern appliances, ample counter space, and an open layout ideal for entertaining. Sunlit living areas with high-end finishes enhance the home’s beauty and warmth. A boater’s paradise, this home includes an 11,000 lb boat lift for effortless access to Sarasota Bay and the Gulf of Mexico. Located just minutes from pristine beaches, championship golf courses, and the upscale shopping and dining of St. Armands Circle, this home offers the perfect blend of luxury and convenience. NO storm damage! Available for an annual rental. Contact us today to schedule a private showing! NO storm damage!

Listing is courtesy of: WAGNER REALTY (941-727-2800)

Listing Agent: Karie Gorgone (941-313-5469)

Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.

Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)

Listing Agent: Chase Moore (727-325-7272)

Remarks: Summer 2026 is available for June, July, and August! Call today! Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of waves just steps from your door, sip your morning coffee with panoramic ocean views, and take in unforgettable sunsets — all from your own slice of paradise. Located directly on the beach, this property offers a true coastal tropical oasis. You're just minutes from Publix for all your grocery needs, and only 1.5 miles from the Longboat Key Bayfront Park, where you can enjoy pickleball, tennis, shuffleboard, basketball, a playground, swings, and scenic walking paths. Looking for shopping and dining? St. Armands Circle is just a 5-mile drive away, offering a celebrated selection of restaurants and boutiques. June, July, August, November, and December are available! Rates are: $10,000 for June, $10,000 for July, $10,000 for August, $10,000 for November, and $10,000 for December. Taxes apply. Call today and book your stay!

Listing is courtesy of: CELLA'S REAL ESTATE INC (941-952-8649)

Listing Agent: Michael Cella (941-952-8649)

Remarks: 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 includes bunk beds for family fun. Accommodating up to 9 guests, the property is just a short stroll to pristine Whitney Beach and nearby fishing docks, with top local restaurants and cafes — like Mar Vista, Shore, Whitney’s, and more — only minutes away. A local owner ensures attentive service to make your stay unforgettable. $10,000 off season/$14,000 season. Leased July 2025, August 2025, March 2026, April 2026

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

Listing Agent: Rinat Sikdar (941-993-9292)

Remarks: Looking for a 3 month renter for January, February, and March or the month of January 2026. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy flooring, this home has it all. Sit outside on the upper deck with a view of the refreshing pool during breezy afternoons or the covered deck downstairs which offers shade while not sunning. Ping pong and bocce ball complete the picture for hours of fun. The dining table sits (6) with (4) breakfast bar seats nearby. Two bedrooms have (1) Queen and (1) twin each, one quest bedroom has a Queen and the master has a King bed, all with large screen televisions.

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

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

Remarks: **This is a 2 month minimum vacation rental** **Availble for all of 2027** Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this remodeled and meticulously maintained pool home boasts nearly 3,000 square feet of living space—including 2,021 square feet on the main level and an additional 942 square feet on the walk-out lower level. As you approach the property, you’ll notice the gentle slope of the lot from the street up to the main entrance, framed by lush palms, mature oaks, and banyan trees. The double-door entry opens to an inviting, open-concept great room that seamlessly connects to a spacious outdoor deck overlooking the backyard and pool area below. The updated, modern kitchen features custom cabinetry, stainless steel appliances, a built-in double oven, and a six-burner Viking gas cooktop—perfect for entertaining. Also on the main level are three bedrooms, including two guest rooms and a full guest bathroom. The expansive master suite offers a large walk-in closet and a well-appointed en-suite bathroom. The lower level, with its wall of sliding glass doors, opens directly to the screened pool deck and a 40-foot pool equipped with a new pump. This level also includes a full bathroom and laundry area. The two-car tuck-under garage offers ample storage space and a small workshop area. As a resident of Bay Isles, you’ll enjoy access to the Private Bay Isles Beach Club, located at 2111 Gulf of Mexico Drive, just across from the community. The club features a pristine stretch of beach, picnic tables, tiki huts, barbecue grills, an ice machine, and storage bins for beach gear. A key fob, included with the rental, is required for access. More information can be found on the Bay Isles website. The base rent for January through April is 11,000 and off months is 9,000

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

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

Remarks: SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the perfect Winter getaway. One visit to this 3BD+Den/2.5BA golf course detached home will have you wanting more! It has been updated in all the newest tones, is fresh, and combined with natural lighting, is so inviting. Pavered drive and lush landscaping and walkway lead you into the foyer entry. The combined living/ dining area is warm and inviting with vaulted ceilings, tile flooring and new comfortable furnishings. The kitchen is designed for entertaining or just relaxing with a marvelous view of the 2nd green. The den is a cozy retreat for TV or for catching up on work or emails in the dinette area. The private and spacious master suite offers ensuite bath and has a seating area to relax and enjoy the views! The second bedroom features queen accommodations and the third bedroom offers twins. All have their own private entrance for a relaxing stay. Additional charges for pool heater use. This marvelous turnkey residence comes complete with gated security, Wifi, inside laundry, 2 car garage, private and community pool and easy access to shopping, dining and cultural arts from St. Armands Circle to downtown Sarasota. Booked Jan 5th - April 5th, 2026.

Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)

Listing Agent: Diann Thelen (941-920-0758)

Remarks: 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 décor throughout. As you walk the stone path to the front door, you will find beautifully manicured landscaping in every direction. This home has many luxury details including a gourmet kitchen which, is equipped with all WOLF appliances, SUBZERO refrigerator, wet bar, wine cooler, Spanish porcelain tile floors, quartz countertops, 10' ceilings, custom PGT high impact doors and windows providing plenty of natural lighting and protection from the elements. The ground level bonus room features a wet bar, which includes a refrigerator, ice maker, dishwasher, sink/garbage disposal acting as second kitchen for the guest suite. In addition you will find a custom-built queen murphy bed, a 65” Smart TV, and four comfortable chairs that overlook the stunning pool deck where you will find you and your family spending a lot of time relaxing and making memories. As you make your way to the second level, either by the elevator or the stairs, you are welcomed by an open and airy floor plan. To the right of the staircase is the main large living room that boasts a large plush “L” shape sofa, a cozy swivel day chair, and a 65” Smart TV. Next to the living room is the immaculate dining room, which brings a beautiful coastal element. The dining table can accommodate up to six comfortably. The living room and dining room share a beautiful balcony with views of the pool and all the lush landscaping surrounding this home. There is outdoor seating that can accommodate up to four comfortably. Adjacent to the dining room, you will find the state-of-the-art kitchen where you can prepare all your favorite meals. As you make your way down the hall from you will find the first two bedrooms. The first bedroom has been designed for the kid at heart, and includes three queen-size beds, a 55” Smart TV, and attached private bath. Next door you will find the second bedroom. This room boasts a queen-size bed, a 55” Smart TV, a private bathroom, and balcony. As you head to the top floor, you will find the master suite, which boasts a king-size bed, a 65" Smart TV, and a private deck with seating for two overlooking the pool. This master bathroom is truly one of a kind and includes two separate vanities, an enormous soaking tub, and a walk-in shower! Rinse off in the outdoor shower before heading into the house! This home has everything you and your family will need to make memories that last a lifetime! Enjoy the provided beach and pool essentials, which include beach chairs, a beach wagon, beach floats, and pool floats. This property is available to rent monthly only. Pool and spa heat available for an additional fee. Furry friends welcome. Small dogs only. No cats. *Taxes and fees not included

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

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