Homes For Sale in Holmes Beach 34217 - 168 homes

Remarks: Income Producing - Turnkey - Fully Furnished - Vacation Rental Property located in the desirable North Beach Village community. 3D tour showing 360 degree views of the home available for a virtual walkthrough. Start generating rental income from day one with this highly successful income property, with over $30,000 in bookings already for 2026 and almost $10K in 2027! Whether you’re searching for a full-time island residence, a seasonal getaway, or a proven income-producing property, this exceptional offering truly checks every box. Experience the best of Anna Maria Island living, where every day feels like a vacation. This property allows weekly rentals, 52 weeks a year, providing maximum flexibility and earning potential. Located in the desirable pet-friendly North Beach Village community—with no size or breed restrictions—residents and guests alike enjoy a relaxed coastal lifestyle, complete with a large community pool ideal for swimming laps or unwinding after a day at the beach. This beautifully decorated condo is nestled within a quiet community and is just a three-minute walk to the sugar-sand shoreline. Enjoy being moments away from charming local shops, popular island restaurants, and all the laid-back character Anna Maria Island is known for. Prefer to leave the car behind? The free island trolley stop nearby makes getting around effortless. Outdoor enthusiasts will appreciate nearby amenities including a dog park, playground, basketball courts, pickleball, and tennis courts, all just minutes away. Inside, this inviting island retreat offers 1,536 square feet of bright, open living space, featuring three bedrooms, two and a half bathrooms, and indoor laundry. Recent updates include a new roof (2025) and a standout primary bathroom unlike any other in the community. The spacious primary suite boasts a large walk-in shower with seating, dual-sink vanity, linen closet, and a private commode area, creating a true spa-like retreat. The home also features hurricane shutters and a hurricane-rated reinforced garage door, offering peace of mind for owners and guests alike. Neutral flooring and soothing paint tones throughout create a calm, coastal atmosphere that both owners and guests will love. Multiple outdoor living spaces enhance the island experience, including a screened-in porch tucked among the trees for added privacy, two large balconies, and a private ground-level deck—perfect for enjoying island breezes and outdoor dining. A large sleeper sofa allows plenty of room for extra guests. On the ground level, in addition to the main living area, you’ll find a generous 10' x 14' bonus space, ideal for a home office, gym, or game room. There is also an oversized 9'6" x 8' owner’s closet/storage room, providing the perfect place to securely store personal belongings while the property is rented. Offered fully furnished and truly turnkey, this exceptional property presents a rare opportunity to own a slice of paradise with outstanding income potential. Whether you’re investing, vacationing, or settling in year-round, this home delivers the ultimate island lifestyle—sun, sand, and serenity just steps from your door. Shared condominium expenses may result in lower overall carrying costs compared to some single-family homes.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)

Listing Agent: Kim Bowersox (407-383-3519)

Remarks: A rare find on Anna Maria Island, this elevated coastal home sits on an expansive 10,000+ square foot corner lot, offering exceptional privacy on multiple sides, an uncommon feature in the heart of Holmes Beach. Enhanced by a new metal roof (2025), newer air conditioning system (2022), storm-rated impact windows and doors, and a newly resurfaced heated pool (2025), this home offers true peace of mind and resort-style living. With weekly rental zoning, this Anna Maria Island real estate opportunity is offered fully turnkey furnished, has recently operated as a short-term rental, and is located just 3 blocks from Anna Maria Island’s sugar sand Gulf Beaches. A perfect blend of island lifestyle with strong investment flexibility. Centrally located in Holmes Beach FL, this quiet neighborhood home is close to restaurants, shopping, coffee shops, and many island attractions. This custom home is far from “cookie cutter.” Custom features include an open-concept layout with 9.5-foot ceilings, soaring tray accents, abundant natural light, luxury vinyl flooring, brand-new carpet in bedrooms, plantation shutters, and a distinctive round formal dining room that captures peaceful and picturesque views down the canal. The chef’s kitchen offers granite countertops and a spacious breakfast bar flowing into the great room, perfect for family nights or an evening of entertaining guests. The private primary suite includes an en-suite bath, a walk-in closet, and continued picturesque views of the canal. Both the primary and additional bedrooms feature built-in closet shelving and organizational systems for added ease. Step outside to a truly rare find in Holmes Beach: an oversized, completely private backyard oasis designed for ultimate relaxation. The outdoor experience begins on the elevated deck, offering the perfect vantage point over the sparkling heated pool, an ideal spot for morning coffee or evening cocktails. Below, a resort-style sunbathing terrace invites you to soak up the sun with plenty of room for intimate outdoor dining or entertaining family and friends. Fully fenced and finished with lush tropical landscaping and low-maintenance artificial turf, this expansive retreat provides the space and privacy rarely found in this area. The property offers convenient access to Sarasota-Bradenton International Airport approximately 40 minutes away, Tampa International Airport about 60-70 minutes, and IMG Academy roughly 25 minutes from the island. Plus a Holmes Beach bonus with City of Holmes Beach boat slip rentals available directly across the street on a first-come, first-served annual lease basis (currently waitlisted) for approximately $750/year.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Brooke Doucett, Llc (941-586-3522)

Remarks: This charming 3 bedroom, 2 bathroom home offers a perfect blend of island living and modern comfort. With spacious outdoor living and multiple screened in balconies its perfect for relaxation and perfect Florida weather. The layout is designed for seamless indoor-outdoor living, ideal for entertaining or relaxing with family. The kitchen is equipped with contemporary stainless steel appliances, ample counter space, and storage, making it perfect for culinary enthusiasts. Each bedroom offers comfortable living with generous closet space. Enhance the feeling of openness and light throughout the home. Mature foliage provides privacy and a tropical feel as well as low maintenance. Huge garage for vehicles, including room for island-favorite golf carts. Only a short stroll from the Gulf of Mexico beaches to enjoy beach walks and nightly sunsets. This is an excellent opportunity for those looking to invest in a slice of paradise with the potential for both personal enjoyment and rental income, permitted for weekly rentals. Whether you're seeking a permanent residence, a vacation home, or an investment property, this home combines comfort with the quintessential Florida lifestyle. See attached list of upgrades.

Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)

Listing Agent: Barbara Sato (941-778-7200)

Remarks: Steps to the Beach: A Deluxe Retreat with Massive Rental Power! Why choose between a vacation home and a smart investment? This stunning, fully remodeled villa offers the best of both worlds. Nestled just a short stroll from the sand, this 2-bedroom, 2-bathroom sanctuary w/ private garage is a masterpiece of coastal design. But the beauty is more than skin deep—this property is a proven earner, generating over $69K in rental income since June 2025 alone. The backyard is a private resort, featuring a heated pool with spa features and a one-of-a-kind custom bar with a cascading waterfall—the perfect 'money shot' for your rental listing. Inside, enjoy 1,300+ sq ft of luxury, sold turnkey furnished for immediate enjoyment or continued rental success. With impact-rated everything and a modernized effective age, this villa is as 'set-and-forget' as it gets. Whether you are looking for a personal paradise or a turnkey business with a $100k+ annual potential, your search ends here.

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Lindsey Strickland (941-737-3491)

Remarks: THIS IS THE ONE! Welcome to Annabella by the Sea. Impeccably built to the highest standards in 2024 by Eason Builders Group. This luxury home is a coastal dream, situated in the heart of Anna Maria Island, featuring 4 stunning bedrooms, 4.5 baths, over 3200 sq ft of refined living space, and multiple covered outdoor spaces, combining elegant comfort with the best of island living. Located in an ideal location, walkable to the sugary beaches of the Gulf, close to dining, shopping, and local attractions. No expense spared on this contemporary gorgeous home with designer finishes throughout, a gourmet kitchen with oversized island, top of the line appliances, huge walk-in pantry, and custom cabinetry. The open concept is perfect for entertaining with a spacious living and dining room that seamlessly connects to a large balcony with more seating. Custom light fixtures, spacious bedrooms with private ensuites, a game room by the pool area and a family room on the second floor ensures there is room to unwind and relax! Last, but not least, the oasis back yard with covered lounge areas, a luxurious pool and spa, lush landscaping and multiple balconies is the perfect spot to hang out after a day at the beach. Or take your party to your roof top deck for sunset and panoramic views. This gorgeous home is spacious in every sense and comes completely furnished with luxury details, curated so all you need to do is bring your clothes. A great rental history, making it the perfect family retreat or an outstanding investment property. Call today to schedule your private showing. Own where your heart already lives!

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Dee Munn (407-346-4422)

Remarks: Discover the epitome of coastal sophistication with this exquisite British West Indies waterfront residence, perfectly nestled on Anna Maria Island. Spanning over 5,000 square feet, this luxurious home is designed for those who love to entertain and indulge in the finer things in life. Step inside to find two lavish primary suites, an elevator, and multiple terraces that offer breathtaking views. The entertainment options are endless with a stylish media room featuring a beverage center, ideal for movie nights or hosting friends. Every corner of this home exudes elegance, from the solid wood cabinetry and custom millwork to the stunning hardwood and travertine flooring. The open floor plan seamlessly connects to an eat-in kitchen, boasting a large central island, double oven, butler’s pantry, and granite surfaces, making it a chef’s paradise. For more formal gatherings, the separate dining room sets the perfect scene. An office or den is conveniently located on the main level, offering a quiet retreat for work or relaxation. Two additional bedrooms share a spacious bathroom complete with a walk-in shower, ensuring comfort for family or guests. Outdoors, the multiple living areas provide serene views of the canal and Bimini Bay, with direct access to the Intracoastal waterway. The lavish outdoor amenities include a saltwater pool with a sun shelf and spa, and a 70-foot dock equipped with a 13,000-pound boat lift, perfect for boating enthusiasts. Entertain in style on the expansive covered lanai, featuring an outdoor kitchen and ample space for gatherings. Additional features such as plantation shutters, a state-of-the-art security system, oversized closets, and a 3-plus car garage enhance the allure of this property. Don’t miss your chance to own this stunning waterfront retreat. Call today for your private viewing and step into a lifestyle of unparalleled luxury.

Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)

Listing Agent: Gregg Bayer (941-799-9096)

Remarks: ~~~~~~PRICE DROP~~~~~~~~ The time to buy your beach house is NOW!! Welcome to Turquoise Beach Bungalow, a thoughtfully reimagined island retreat designed for effortless second-home living. Completely renovated inside and out in 2024–2025, this home blends timeless island character with modern comfort, quality craftsmanship, and true lock-and-leave ease. From the moment you arrive, everything has already been done for you. A new seamless metal roof, fresh stucco exterior, updated systems, all-new appliances, three new AC units, and a tankless water heater provide peace of mind when you are away and comfort when you are here. Inside, terrazzo floors set a relaxed coastal tone throughout the open and expanded layout. A newly added approximately 350-square-foot primary suite offers a private retreat with a beautifully finished ensuite bath and both indoor and outdoor showers, perfect after a day at the beach or for enjoying quiet island evenings. The remodeled kitchen features quartz countertops, stainless steel appliances, and generous storage, flowing easily into the main living areas and a flexible third bedroom currently used as a second lounge space. The laundry room is conveniently located just off the patio, ideal for beach days and easy transitions indoors. Outdoors, a covered patio creates an inviting space to relax or entertain, while the oversized backyard offers ample room to add a pool and expansive outdoor living area. Whether you envision quiet mornings, sunset gatherings, or extended seasonal stays, the space is ready to adapt to your lifestyle. Set in a peaceful neighborhood just a short walk to the Gulf beaches and the Intracoastal Waterway, the location balances privacy with convenience. Centrally positioned between the island’s two bridges, you are close to shops, dining, and island favorites. An added bonus is the opportunity to lease nearby boat slips through the City of Holmes Beach, just a block away on Avenue B. Being sold turnkey furnished, Turquoise Beach Bungalow is ready for you to arrive, unwind, and enjoy island life from day one. Schedule your private showing and experience how seamless owning a second home can be.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Kathy Harman (941-900-9828)

Remarks: Hidden gem on North Point Drive in one of the most exclusive communities on Anna Maria Island. This beautifully remodeled 3 Bed, 3.5 Bath two story home is nestled on a quiet cul-de-sac, offering privacy and tranquility just steps away from the stunning waterfront. The bright and airy layout features vaulted ceiling in the living room and loft area, creating an inviting atmosphere for relaxation and entertainment. The gourmet kitchen, the heart of the home, boasts custom tile and solid wood cabinetry, marble backsplash, a six-burner gas range and an expansive island, perfect for culinary enthusiasts. Each bedroom is an ensuite with walk-in closets, offering privacy and comfort. The primary suite, located on the main level, features a luxurious walk-in shower, built -in medicine cabinets, laundry bin cabinetry, and a double sink vanity. There is a dedicated A/C system for each floor. Step outside to enjoy a large patio that leads to your private dock with a new 12,000 pound boat lift, making it easy to access the beautiful waters of Tampa Bay. Additional outdoor amenities include a kayak lift, fish cleaning station, outdoor shower and kayak storage rack. The property is surrounded by lush, tropical landscaping, enhancing its curb appeal and creating a serene environment. Additionally, a secure gated area for your pets ensures a safe space to play. Community amenities include access to a pool and tennis/racquetball courts, perfect for an active lifestyle. With an elevation of more than 8 feet above base flood elevation, your home is safe and secure, potentially qualifying for favorable flood insurance rates. Don't miss this rare opportunity to own a piece of paradise on Anna Maria Island! Schedule your private showing today.

Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)

Listing Agent: Gregg Bayer (941-799-9096)

Remarks: Charming Coastal Cottage in Holmes Beach. Welcome to this newly and meticulously remodeled coastal retreat, ideally located in the heart of Holmes Beach. This one-of-a-kind, artsy beach cottage blends timeless charm with modern elegance and smart technology. Step through the inviting rain glass double doors into a spacious open-concept living, dining, and kitchen area, where a dramatic lighted cupola and vaulted ceilings create a stunning first impression. A custom shell stone fireplace with a wood mantle adds warmth to the cozy seating area—perfect for relaxing or entertaining. The chef’s kitchen is a true showstopper, featuring an oversized, lighted quartz island with seating, beadboard cabinetry, and a custom wave-patterned glass backsplash. High-end appliances include an ILVE Majestic 4-burner gas stove with griddle, GE Café refrigerator, wine fridge, and porcelain farm sink—all designed with entertaining in mind.Craftsmanship continues throughout with custom millwork, shiplap accents, paneled walls, and solid-core doors. Oversized sliding glass doors open to reveal a tropical backyard oasis, complete with a free-form heated pool and spa, paver patio with artificial turf. The lush, mature landscaping with up lighting show off the tall palm trees, perfect for a evening cocktail party under the stars. The southern-facing yard is perfect for dining, lounging, and soaking up the sun. Each of the three bedrooms and 2.5 baths showcases custom chrome period fixtures, retro-inspired sinks, and designer details. Tech-savvy buyers will love the smart home features, including Lutron lighting controls, LED lighting, Sonos sound system, security cameras, and plantation shutters. The property includes a 250-gallon buried propane tank serving the on-demand water heater, gas grill, pool heater, and stove. It’s also generator-ready with existing plumbing and wiring in place. There is city dockage close by for boating enthusiast's This extraordinary home offers a rare blend of beachy charm and luxurious amenities—an absolute must-see!

Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)

Listing Agent: Gregg Bayer (941-799-9096)

Remarks: Set within the desirable North Point Harbour enclave of Key Royale in Holmes Beach, this impeccably reimagined waterfront residence captures the essence of coastal living, where clean architectural lines, curated interiors, and uninterrupted water vistas converge. From the moment you enter, every space is thoughtfully oriented to frame expansive views of Bimini Bay and Tampa Bay, creating a dynamic yet tranquil backdrop that evolves throughout the day, from soft morning reflections to vivid Gulf Coast sunsets. Updates include hurricane windows and sliding glass doors, new roof, wood look tile throughout, new composite dock and 20,000# lift. The floor plan is thoughtfully designed to balance privacy with hospitality, anchored by two primary suites, offering exceptional flexibility for hosting guests or extended stays. The main-level suite provides convenience and accessibility, while the upper-level primary and additional bedrooms create a quiet retreat with elevated water views. At the heart of the home, a statement kitchen serves as both a culinary showpiece and social hub. Outfitted with a Monogram refrigerator and gas range, the space is complemented by an expansive Cambria quartz island with seating for six. Two wine refrigerators are thoughtfully integrated, elevating the entertaining experience and seamlessly connecting to the dining and living areas. Beyond the interiors, the home extends into an exceptional waterfront lifestyle. A newly constructed dock with a 20,000-pound lift caters to serious boating enthusiasts, while the property offers ample space to design a custom poolscape tailored to your vision. The oversized two-car garage offers generous additional storage, ideal for a golf cart, beach essentials, bicycles, and coastal lifestyle gear. Directly across the street, residents enjoy convenient access to North Point Harbour's heated pool, as well as a tennis and pickleball court adding an additional layer of resort-style living just steps from your front door. Residents enjoy the close proximity to the sugar-white sand beaches of Anna Maria Island, the restaurants, art galleries and shops in Holmes Beach. Other nearby amenities include dog park, public tennis/pickleball courts, basketball, skate park, library and soccer fields. Ideally positioned just moments from the fairways of Key Royale Golf Club’s private par-32, nine-hole course, optional membership provides access to golf, dining, and a vibrant social scene. Downtown Bradenton, Sarasota, SRQ Airport, Tampa Airport and St. Pete/Clearwater Airports are all within an hour drive away. Residents and visitors appreciate all the opportunities to enjoy the theatre, art fairs, farmers markets, concerts, boating, fishing and shopping that is convenient for the Florida lifestyle. This is more than a home. It is a lifestyle of relaxed coastal luxury, effortless entertaining, and a constant connection to the water on Anna Maria Island. BEAUTIFUL FURNISHINGS OF THIS HOME ARE NEGOTIABLE.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Linda Moore (941-737-3581)

Remarks: Back on the Market - Truly a remarkable property, designed in the style of a charming New England Coastal Inn, this intimate 12-unit, three-story beachfront retreat blends timeless character with modern convenience. An elegant staircase and elevator provide access to Unit #6, ideally positioned on the second floor. This spacious 2-bedroom, 2.5-bath residence features beautiful original wood flooring and crown molding throughout. There are not one—but two—private balconies offering pool views, sweeping Gulf vistas, and unforgettable Sunset skies. One balcony extends from the living room, while the second is accessed from the primary suite, creating the perfect setting for morning coffee or evening relaxation. Enjoy a good book or a glass of wine while listening to the Gulf waves breaking across the sand. Inside, you’ll find built-in closets, an in-unit washer and dryer, and a layout designed for comfort and functionality. The Mainsail Inn operates as a condo-hotel, allowing owners up to 120 days of personal use a year while the professional on-site management team actively rents the unit the remainder of the time. With its prime location directly on the sugar-sand beaches of Anna Maria Island, occupancy levels are typically strong—making this not just a beachfront getaway, but a smart income-producing asset. Even better, ownership means enjoying four months each year in your own beachfront retreat without paying nightly rental rates—while rental revenue often offsets the operating expenses. Offered turnkey, this unit includes everything—furnishings, décor, beach equipment, kayaks, paddleboards, and more. Simply bring your swimsuit and start enjoying beachfront living at its finest. This is the kind of property that checks every box: lifestyle, location, and long-term value.

Listing is courtesy of: WAGNER REALTY (941-383-5577)

Listing Agent: Ed Taaffe (636-346-6165)

Remarks: Sweeping Gulf sunsets, sugar-white sand, and the unmistakable charm of Anna Maria Island — now offered at a refreshed price. Perched on the 5th floor of the Martinique, this rarely available beachfront residence puts the entire horizon at your feet, where turquoise water stretches as far as the eye can see and the nightly sunset show never plays the same way twice. Floor-to-ceiling glass pulls the Gulf straight into the open living space and primary suite, with sunlight shifting from gold to rose to amber across the day. Inside, a crisp coastal palette of stone countertops, shaker cabinetry, and a generous breakfast bar makes entertaining effortless, while two spacious bedrooms and two full baths offer comfort and privacy for family and guests. Beyond your door, the Martinique delivers true resort living — heated beachfront pool, tennis courts, and direct access to powder-soft sand and the calm, shimmering Gulf. A deeded garage and private storage keep paddleboards, bikes, and beach gear at the ready. And then there's the island itself. Anna Maria's seven-mile ribbon of old-Florida charm is yours to roam: hop the free island trolley to Pine Avenue's boutiques and cafés, cast a line off the beach, paddleboard the bayside flats, or settle in at the Sandbar for dinner with your toes in the sand. With no high-rises and a pace all its own, Anna Maria stays quietly, beautifully unchanged — the kind of place where seasons melt into one long coastal summer. A refreshed price on one of the Gulf's most coveted addresses. This is your spring to claim it.

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Darcie Duncan (941-779-0304)

Remarks: Enter into luxury coastal living with this beautifully remodeled two-bedroom, two-bath beachfront condominium at sought-after Gulf Sands on Anna Maria Island. Directly on the Gulf of Mexico, this rare Gulf-front unit offers sweeping, unobstructed views of the beach and sunsets from your private balcony. Recently upgraded with a high-end remodel, the condominium features modern coastal furnishings, a gourmet kitchen with stone countertops and stainless steel appliances, spa-inspired baths and elegant flooring throughout. Sold fully furnished, it’s move-in ready. Enjoy the heated beachfront pool, private beach access, and convenience of an elevator and assigned parking. Gulf Sands is a low-density, well-maintained complex ideal for full-time living, a second home or investment property. Live the island lifestyle—near the sand, dining, shops and everything Anna Maria Island has to offer.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Laurie Mock (941-232-3665)

Remarks: Directly across the street from the beach with Gulf water & beach views. This updated, turn-key furnished unit is centrally located on the island with easy access to the beach, several restaurants and shopping. "Beach Townhouses" is a smaller complex with just 11 units in total offering a large, heated pool, spacious private carports & storage located on the ground level. Each unit offers TWO balconies facing the beach. The one off of the main floor living space is larger & screened. The additional, primary bedroom balcony is covered & open air. Both are a great place to catch the sunset or to enjoy your morning coffee! The master suite offers an updated master bath, dressing area and a walk-in closet. This comfortably furnished unit is being sold turn-key furnished for convenience of a future vacation rental. There are three storage closets in the carport. A smaller, private patio is located pool-side for grilling & al fresco enjoyment. Easy access to the Manatee Bridge to avoid traffic to the mainland during our busier seasons. Want to be right in the heart of A.M.I., schedule a showing today!

Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)

Listing Agent: Marianne Norman-Ellis (941-685-3393)

Remarks: Effortless Island Living at this elevated 3BD/2BA home, where breezy interiors and sunlit spaces create the perfect island escape just steps from the sand. Located in a highly desirable weekly rental zone, this property offers exceptional flexibility and income potential. Inside, the living and dining area welcomes you with abundant natural light and easy access to the expansive front deck. The kitchen features generous counter space and a breakfast bar, making entertaining effortless, while the split bedroom layout provides comfort and privacy. Downstairs, an oversized garage delivers convenience with tandem space for up to four vehicles, along with plenty of room for beach gear, bikes, and additional storage. The low maintenance outdoor space lets you spend more time enjoying the coastal lifestyle, whether you're heading out for sunset walks or relaxing in the ocean breeze from the deck. With its unbeatable location, strong rental appeal, and inviting coastal feel, this property checks lots of the boxes. Bring your decorator touches and create your personal island vibe. Easy access on and off the island, close to shopping, dining, a trolley stop and the beach is right at your back door. What more or you waiting for? Make this your perfect little slice of island life!

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Darcie Duncan (941-779-0304)

Remarks: STEPS FROM THE GULF – LUXURY SIX-BEDROOM COASTAL RETREAT IN HOLMES BEACH | Discover Summer’s Retreat, an architectural masterpiece where luxury meets the legendary white sands of Anna Maria Island. This remarkable six-bedroom, six-and-a-half-bath coastal estate represents one of the island’s most coveted properties—a rare find featuring six private en-suite bedrooms that seamlessly blend family sanctuary with proven investment excellence. Step into an oasis of sophisticated design where every detail has been thoughtfully curated. The expansive open-concept living space flows effortlessly from room to room, bathed in natural light that dances across premium finishes. The gourmet chef’s kitchen stands as the heart of the home, showcasing lustrous quartz countertops, professional-grade stainless steel appliances, and an impressive bar-top island that beckons both intimate conversations and grand celebrations. Four private balconies serve as personal retreats, each capturing the gentle Gulf breezes and offering front-row seats to nature’s daily theater. Crown this experience atop the spectacular rooftop deck, where panoramic sunsets paint the sky in brilliant oranges and pinks over the endless Gulf waters. The outdoor experience rivals any world-class resort. Immerse yourself in the heated saltwater pool with its luxurious sun shelf, perfect for lounging with a morning coffee or evening cocktail. The therapeutic spa provides the ultimate relaxation after days spent exploring island treasures. Tropical landscaping creates an intimate paradise, while the expansive covered patio transforms into an entertainer’s dream. The dedicated outdoor dining area and professional grilling station make every meal an event, whether hosting friends or enjoying quiet family moments under the stars. Location is everything, and Summer’s Retreat delivers the extraordinary. Literally steps across the street from pristine Manatee Beach access, your morning walk to sugar-sand shores takes mere moments. The vibrant Anna Maria Island Beach Café becomes your neighborhood gathering spot, while playgrounds ensure endless fun for families. The island’s charm extends beyond your doorstep—boutique shops, acclaimed restaurants, and the complimentary island trolley create a car-free lifestyle where every amenity is within reach. This isn’t just a home; it’s a gateway to the Anna Maria Island experience. Summer’s Retreat has established itself as a premier vacation rental destination, consistently generating exceptional returns for discerning investors. The unique combination of six en-suite bedrooms, luxury amenities, and unbeatable location creates unparalleled demand among visitors seeking the ultimate island experience. This property offers the rare opportunity to enjoy your own slice of paradise while building wealth through one of Florida’s most sought-after rental markets. Whether you envision lazy mornings on private balconies, sunset celebrations on your rooftop deck, or poolside gatherings with loved ones, Summer’s Retreat transforms every day into a vacation. This is more than a home—it’s your personal resort, your investment sanctuary, and your gateway to the incomparable Anna Maria Island lifestyle. Experience the extraordinary. Your coastal legacy awaits.

Listing is courtesy of: ENGEL & VOLKERS ST. PETE (727-295-0000)

Listing Agent: Leisa Mohler-Erickson (239-789-7106)

Remarks: Mediterranean-inspired coastal luxury just one block from the Gulf—this fully furnished, elevated single-family villa, “Island Oasis,” offers no HOA, complete privacy, and proven storm resilience with no damage to upper living areas. Solid construction, turnkey condition, and major system updates provide immediate peace of mind, especially with income projections between 153-193k annually, for those interested in renting. This exceptional Anna Maria Island retreat comfortably accommodates 8+ guests, featuring two king suites, a third bedroom suite with two queen beds, and additional sleeping space in the great room—ideal for personal use, multigenerational living, or income-producing potential. Recent upgrades include new roof (2024), refrigerator (2024), dishwasher (2025), washer/dryer (2024), AC units (2020 & 2017), and water heaters (2025 & 2019), along with a resurfaced pool with new coping, pavers, heater, and pump. Inside, the home showcases light-filled interiors, soaring ceilings, crown molding, and natural wood accents, blending refined coastal design with relaxed island comfort. The open-concept kitchen features wood cabinetry, tile backsplash, an eat-at island, and newer stainless appliances, flowing seamlessly into the main living and dining areas. Glass sliders open to a front piazza and private pool courtyard, creating effortless indoor-outdoor living. The primary suite offers a private balcony and a spa-style bath complete with a clawfoot soaking tub and walk-in shower, delivering a true owner’s retreat. Above it all, a rooftop terrace captures 360° sunrise and sunset views, with peek-a-boo Gulf and Bay views, setting the stage for unforgettable evenings in the delightful island breeze. Step outside and experience the Florida lifestyle—sun-drenched pool days, shaded terraces, and lush tropical landscaping create a private oasis just moments from the beach. A short walk leads you to the soft white sands of the Gulf, while nearby favorites like Skinny’s, Manatee Beach, Pine Avenue, boutique shopping, waterfront dining, and the free island trolley make island living effortless. Elevated, meticulously maintained, and offered fully furnished, this is a rare opportunity to own a resilient, income-capable coastal home in one of Florida’s most sought-after destinations. Anna Maria Island living at its finest—sun, sand, and effortless coastal luxury await.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)

Listing Agent: Jo-Lee Mansfield (843-303-7463)

Remarks: Step into effortless luxury with this meticulously renovated canal-front retreat, ideally located on 100 feet of waterfront, on an 11,543 sq ft lot in the heart of the Key Royale community. Designed for relaxed coastal living, this beautifully updated 3-bedroom, 3.5-bath home offers the perfect blend of style, comfort, and waterfront lifestyle. The home has a chef-inspired kitchen featuring wood cabinetry, quartz countertops, a gas range, wall oven, wet bar with wine refrigerator, and a generous center island perfectly suited for both everyday living and elegant entertaining. Walls of sliding glass doors bathe the interior in natural light and open to a private outdoor oasis, creating a seamless indoor-outdoor flow. Two of the bedrooms have private ensuite baths, including the primary bedroom which features a spacious bedroom with an en-suite bath with a soaking tub, a walk-in shower and an outdoor shower providing comfort and privacy. Outside, enjoy the resort-style pool designed for lounging in both sun and shade, or take in peaceful canal views framed by lush tropical landscaping.  A new irrigation system and new elegant landscape lighting have also been installed. A true boater’s dream, the property features a private dock with electric and water, plus a 10,000 lb boat lift and kayak launch, offering quick access to the sparkling waters of Bimini Bay, Tampa Bay and beyond. Additional updates include a roof installed in 2017 for added peace of mind.  Just a short stroll or bike ride from Anna Maria Island’s sugary beaches and moments from charming shops, dining, and island attractions; the location is as exceptional as the home itself. Residents of Key Royale have the option to join the private Key Royale Club, a 9-hole golf course with a clubhouse, creating a lifestyle that perfectly balances boating, golf, and island leisure. Bring your boat, fishing poles, golf cart, and clubs and start living the island lifestyle you’ve been dreaming of. This is a rare opportunity to own a truly special slice of waterfront paradise.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Hannah Hillyard (941-744-7358)

Remarks: Tucked within the exclusive waterfront community of Key Royale on Anna Maria Island, this beautifully renovated canal-front residence offers an exceptional blend of island charm, privacy, and effortless island living. Designed to embrace the Florida lifestyle, the home is centered around a spectacular pool courtyard, where almost every room opens to the expansive outdoor living space, creating a seamless connection between indoors and out. Bathed in natural light due to its desirable southern exposure, the home invites sun-filled days by the pool and tranquil evenings under the coastal sky. The thoughtfully designed split floor plan features a private primary suite with ensuite bath, along with two additional guest bedrooms and a well-appointed second bathroom, offering comfort and flexibility for family and visiting guests. The home offers a new roof and seawall was replaced in 2006, ensuring lasting quality and peace of mind for years to come. Ideally situated on a deep-water canal, the property provides a 10,000 lb boat lift and dock with water and electric. Direct access to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, make it a dream for boating enthusiasts and lovers of life on the water. Also, located just moments from Anna Maria Island’s world-renowned beaches, charming boutiques, and acclaimed dining, this residence captures the essence of luxury coastal living in one of the island’s most coveted neighborhoods. Don't miss this extraordinary opportunity to experience the elegance, serenity, and waterfront lifestyle that make Key Royale truly exceptional.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Becky Sirigotis (941-201-8000)

Remarks: Condo on Anna Maria Island, FULLY FURNISHED 2 bed 2 bath, perfectly situated within 1 MILE OF THE BEACH. HIGH AND DRY! Enjoy the breezy GLASSED IN FLORIDA ROOM overlooking the pool or close the sliding glass windows to enjoy the view with air conditioning. Front entrance opens into the shady SCREENED-IN LANAI, LAUNDRY CLOSET is to the left with stackable WASHER/DRYER. Convenient STORAGE CLOSET/WORKSHOP to the right. Original parquet flooring in the foyer. Kitchen has a large pass through opening to the dinning room. Home provides a spacious dwelling area with living/dinning room combo. RECENT UPDATES: ROOF, HVAC, WATER HEATER, and CARPET. Remote controlled ELECTRONIC HURRICANE SHUTTERS for extra protection. Community includes a private BOAT RAMP, BOAT DOCK that doubles as a fishing pier, 2 HEATED POOLS, SPA, TENNIS COURTS, KAYAK/PADDLEBOARD STORAGE and open parking. MAINTENANCE FREE LIVING: CONDO FEE INCLUDES: cable tv, high-speed internet, water, sewer, trash, ground maintenance, exterior maintenance, master insurance, pool, spa and more. Just a 2-minute walk to the CENTRAL PARK which features a DOG PARK, PICKLEBALL COURTS, SKATE PARK, BASKET BALL, BALL PARK, PLAYGROUND and OUT DOOR FITNESS CENTER. Minutes away from sandy beaches and sunshine, the entire island is GOLF CART FRIENDLY, making it easy to explore. Enjoy a cozy atmosphere with local bike shop, restaurants, shopping options, and multiple access points to the beach.

Listing is courtesy of: SANTANA AND COMPANY REAL ESTATE (941-226-9664)

Listing Agent: Ruth Santana (941-226-9664)