Holmes Beach Homes For Sale & Real Estate - 164 homes

Remarks: Under contract-accepting backup offers. Turnkey Coastal Duplex | 5-Star Short Term Rental | Proven Rental Income | Short stroll to the Beach. Rarely does a property this well-positioned come to market. This elevated, fully furnished duplex in the heart of Holmes Beach is an established, high-performing short-term rental with a 5-star Airbnb rating and verified income history available upon request. Two private residences, each offering 2 bedrooms, 2 bathrooms, private entrances, and open-concept living with coastal finishes, create a truly flexible investment opportunity. Ideal for maximizing rental income, offsetting ownership costs by occupying one unit, or enjoying as a vacation home that performs. Just a two-minute walk to the beach, this property benefits from strong and consistent guest demand. Year-to-date rental performance reflects this demand, with approximately $50,000 in gross bookings through March 2026, demonstrating strong early-year performance and consistent booking momentum; detailed financials available upon request. Covered parking and generous storage beneath the elevated structure add convenience for both guests and owners. A conceptual rendering for a pool and outdoor lounge is attached, offering clear upside potential, subject to permitting and buyer verification. Proven income, 5-star reputation, premier location, and weekly rental zoning make this a compelling investment opportunity.

Listing is courtesy of: AMI REAL ESTATE INC (941-447-9663)

Listing Agent: Debbie Hynds (941-447-9658)

Remarks: Welcome to your slice of paradise on beautiful Anna Maria Island! This 3-bedroom, 2-bath island retreat is ideally located just 2.5 blocks from the sugar-sand beaches of the Gulf of Mexico, offering the ultimate coastal lifestyle in one of Florida’s most sought-after destinations. Designed for relaxation and entertaining, the home features an amazing ground-level pool with spa — your own private tropical oasis perfect for soaking up the Florida sunshine or unwinding after a day at the beach. The spacious layout comfortably accommodates family and guests, making every stay feel like a vacation. Enjoy being within walking distance to all that Anna Maria has to offer — charming local shops, great dining, grocery options, and more. Leave the car behind and embrace the true island lifestyle. In addition to being a wonderful personal getaway or primary residence, this property is a great rental home with strong appeal to vacationers seeking location, comfort, and exceptional outdoor living. Its proximity to the beach, walkability, and desirable pool/spa amenities make it highly attractive for short-term rental opportunities. Whether you're looking for an island escape, investment property, or both — this home delivers the very best of Anna Maria Island. Come live your Anna Maria Life!

Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)

Listing Agent: Billi Gartman (941-545-8877)

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: Imagine waking up to views of sugar sand beaches and the turquoise waters of the Gulf. Imagine no longer as you can enjoy this beachfront lifestyle from this 2 bedroom, 2 bath condo in the Beachfront Condominium complex, Tiffany Place. From the moment you enter the unit you will realize its many upgrades: the polished porcelain tile in the foyer and kitchen, the engineered hardwood flooring throughout the remainder of the unit, the plantation shutters, new kitchen cabinets, Jenn Aire Range, stainless steel appliances, remodeled bathrooms and custom cabinets in the primary bedroom. In 2022 a new air conditioner and electric panel were installed and a new hot water heater in 2025. In 2023, all the windows were replaced with Hurricane Impact proof windows, which prevented any damage from the two 2024 hurricanes and provided a discount in insurance and lowered AC costs significantly. As the condo is in the north wing of the complex, you can enjoy the morning sun while drinking your coffee on the balcony and comfortable shade for your afternoon tea or cocktails. The unit has 2 additional storage closets. Tiffany Place is close to the free Island Trolley which can take you to the many unique shops and restaurants on the island and the Library. Or stay put and just enjoy the beachfront living from your new home. .

Listing is courtesy of: A PARADISE INC REALTOR (941-778-4800)

Listing Agent: Helen Ross (941-524-8214)

Remarks: One or more photo(s) has been virtually staged. Welcome to Shell Point, a lovely waterfront community in the heart of Holmes Beach. If extra space is what you need this unit has it with the back lanai that is all remodeled part of the air conditioned space. This lovely updated condo is conveniently located near the Holmes Beach Boat ramp, tennis courts, basketball courts , dog park, and all within a short stroll to shopping, fabulous dining and of course the beautiful beaches of Anna Maria Island. This lovely 2 bedroom 2 bath unit has been wonderfully updated with beautiful wood grain tile floors, all new appliances, trim, doors, kitchen cabinets, bathroom cabinets, lights, and ceiling fans. It also boasts new window treatments, and hurricane windows and doors as well. This little "gem" of an island retreat, has extra interior space (extra square feet) with the bonus area that is located off of the living room. This air conditioned interior space has beautiful natural light just pouring in all morning and offers a back door to access the community pool and courtyard which has walking paths. A perfect space that can be used as an office space, reading space, entertainment space , or just a nice gathering space to rest and sip on your morning coffee. This unit is all brand new and just waiting for you to start making it your new island retreat. Washer Dryer hookup can be reinstalled per Lapensee Plumbing.

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

Listing Agent: Michelle Laade (941-737-9662)

Remarks: Tucked away on a quiet, picturesque street in the heart of Holmes Beach, this ELEVATED WATERFRONT retreat offers a rare private coastal sanctuary. Perfectly positioned on a sprawling 225-foot waterfront SAILBOAT-DEPTH CANAL with NO FIXED BRIDGES and DIRECT ACCESS to Bimini Bay, the Intracoastal Waterway, and the shimmering GULF OF MEXICO. Wrapped in lush, tropical landscaping and framed by a natural mangrove shoreline, a 40+ ft TimberTech COMPOSITE DOCK stretches gracefully into the water; ready to welcome your large boat or sailboat. What sets this home apart is not just its breathtaking setting, but the peace of mind it offers. ELEVATED and STORM-TESTED, this home proudly boasts ZERO HURRICANE DAMAGE - a true rarity on the island. Built with an impressive LIST OF UPGRADES for ultimate resilience: breakaway garage walls REINFORCED with CONCRETE SUPPORTS, a 2023 standing seam ALUMINUM ROOF with underlayment that is MIAMI-DADE STANDARDS, HURRICANE-IMPACT windows and doors with UV protection, and hidden vent soffits and fascia. Step inside and feel the relaxed elegance of this coastal gem. SUNLIGHT floods through every room, dancing off the stunning plank-style porcelain tile floors and creating a warm, inviting atmosphere. The OPEN CONCEPT great room flows seamlessly into a beautifully updated kitchen where your inner chef can run wild. Outfitted with rich maple cabinetry, sparkling Quartz countertops, and top-tier stainless steel appliances. The oversized walk-in pantry is perfect for keeping all your culinary essentials tucked away. The home's bathrooms echo the same attention to detail, featuring gorgeous tilework, granite countertops, upgraded Toto commodes, and brand-new copper piping and plumbing (2025). Every corner has been meticulously cared but it’s the outdoor living that truly sets this property apart. Your private backyard oasis was designed for both relaxation and unforgettable entertaining. Expansive WRAP-AROUND DECKING, crafted from premium materials and beautifully maintained, offers plenty of space to gather with family and friends. The FENCED IN DECKING also is perfect for pets to roam safely, while the CUSTOM KAYAK LAUNCH invites spontaneous paddles through the tranquil canal waters. Dreaming of a pool? APPROVED PLANS are ready and waiting to transform this outdoor space into your personal tropical paradise. Down at the dock, life slows down. Watch dolphins play, drop a line, or simply sip a cool drink as the sun melts into the Gulf horizon. The wide canal offers ample space for larger vessels - a true rarity on the island. Additional features include a spacious 3-CAR GARAGE with TWO LARGE STORAGE areas perfect for paddleboards, fishing gear, or even a golf cart. Conveniently, a 50-amp outlet has been installed for a RV, boat lift or even a hot tub. Ample guest parking is a major plus when it comes to this property and could even accommodate a RV, boat with trailer or whatever your heart desires! Plus a proactive termite protection system. Best of all? This serene retreat is just a short stroll to the sugar-sand beaches of Anna Maria Island, charming local shops, and island-favorite restaurants - all easily accessible via the free island trolley. Whether you’re searching for a full-time coastal residence, a seasonal getaway, or a savvy investment (zoned R-1 with 30-day minimum rentals), this home checks every box. Come experience the magic of Holmes Beach waterfront living where every day feels like a vacation.

Listing is courtesy of: KW SUNCOAST (941-792-2000)

Listing Agent: Mike Polachek (941-524-0241)

Remarks: One or more photo(s) has been virtually staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home use as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof was installed in 2025, and the air-conditioning unit in 2022. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.

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

Listing Agent: Shellie Young, Pa (941-713-5458)

Remarks: Beautifully renovated FURNISHED SECOND FLOOR bayfront condominium offering expansive, unobstructed views of Anna Maria Sound in the highly desirable Westbay Point & Moorings community. Positioned to capture sweeping water vistas, this residence delivers the quintessential Florida waterfront lifestyle with sunrise and sunset views, gentle bay breezes, and panoramic scenery visible from nearly every room. The interior has been thoughtfully updated with wood-look tile flooring, two remodeled bathrooms and a guest bath featuring glass-enclosed shower doors. The bright, coastal-inspired kitchen showcases white cabinetry, quartz countertops, and stainless steel KitchenAid appliances, creating an open, airy space ideal for entertaining. Roof and air conditioning system were replaced in 2025 adding comfort and peace of mind. In 2020, the screened lanai was enclosed with HURRICANE IMPACT RATED WINDOWS, enhancing year-round living while maintaining stunning waterfront views. French doors lead directly to the primary suite, where tranquil bay views set the tone for relaxation. The elevated second floor vantage point that truly sets this home apart. Outdoors Westbay Point & Moorings offers resort-style amenities, including tennis and pickleball courts, a heated waterfront pool, a second pool with spa. The community is situated on a private peninsula with lush, park-like tropical landscaping and enjoys one of the highest elevations on Anna Maria Island, a notable advantage for coastal living. The Association is fully reserved, professionally managed with a long-term on-site manager, and the property includes established rental history, with multiple rentals already in place for 2026. The Holmes Beach dog park, skate park, basketball, tennis and pickleball, public boat launch, playground and community activities are just around the corner. The public library, many restaurants, art galleries and shops are very convenient to this location. The world famous sandy beaches of Anna Maria Island are a short drive, bike ride or stroll away. A rare opportunity to own a bayfront residence on Anna Maria Island combining luxury updates, resort amenities, and enduring rental appeal.

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

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

Remarks: BEACHY KEEN… Just steps from the pristine shores of Anna Maria Island, this exceptional townhome is ideal as a weekend escape, a seasonal retreat from Old Man Winter, or a smart investment while retirement plans are still taking shape. Whether you’re tired of renting, dreaming of a coastal getaway, or looking to diversify with Florida real estate, this property checks all the boxes. Inside, you’ll find an updated kitchen designed to delight the family chef, featuring newer stainless-steel appliances, rich granite countertops, and classic shaker cabinetry. Stunning Brazilian rosewood flooring flows throughout the open, inviting floor plan, complemented by a dedicated dining area perfect for relaxed gatherings. A conveniently located first-floor powder room offers added convenience for guests. The expansive lanai off the living area is ideal for outdoor entertaining and provides easy access to the community pool. Upstairs, two spacious ensuite bedrooms each feature a private bath and their own balcony—perfect for morning coffee or unwinding at the end of the day. A two-car garage offers ample space for vehicles and other island essentials. Located less than 500 yards from the Gulf, your new home away from home invites daily beach walks, refreshing coastal breezes, and spectacular sunsets. Enjoy the island’s charming shops, restaurants, and community amenities including tennis, pickleball, and a baseball field. Come for the weekend, stay for the season, or plan for the future—either way, you’ll be glad you made this move.

Listing is courtesy of: FINE PROPERTIES (941-782-0000)

Listing Agent: Richard Capps (941-920-7500)

Remarks: One or more photo(s) has been virtually staged. This is your golden moment. Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home or to use as a weekly rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.

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

Listing Agent: Shellie Young, Pa (941-713-5458)

Remarks: Under contract-accepting backup offers. Positioned on a naturally elevated homesite for enhanced drainage and reduced flood exposure, this custom-built Anna Maria Island retreat delivers the perfect blend of luxury, flexibility, and proven investment potential. Offered turnkey furnished, the residence features 4 bedrooms, 3 full baths, and a layout designed for effortless full-time living or high-performing vacation use. The light-filled main living level showcases soaring cathedral ceilings, an open-concept great room, and retractable glass doors that create seamless indoor-outdoor living to the expansive deck. The chef’s kitchen is built to impress with double ovens, commercial-size refrigerator, custom cabinetry, soapstone countertops, large island seating, and a brand-new ZLINE gas cooktop, all enhanced by suspended track lighting. Recent improvements include fresh interior and exterior paint, fresh sod and landscaping, an upgraded irrigation system, and a new pool heater and pump — delivering true move-in-ready peace of mind. The private primary suite offers a balcony retreat, walk-in closet, soaking tub, and walk-in shower. Two additional upstairs guest rooms share a spacious bath, while the fourth bedroom on the lower level provides direct pool access and an additional full bath — ideal for guests or multi-generational living. Outdoor living steals the show with a heated pool and spa, waterfall feature, gas firepit, built-in seating, and lush tropical landscaping for maximum privacy and year-round enjoyment. Zoned R1 with 30-night minimum rentals and a strong established rental history, this property offers exceptional flexibility for personal use, seasonal escapes, or income production. Located moments from the Gulf beaches, dining, and shopping of Anna Maria Island, this elevated, furnished coastal home is the total package.

Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)

Listing Agent: Jerry Gemmecke (317-445-2434)

Remarks: One or more photo(s) has been virtually staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated one-bedroom, one-bath unit is a first-floor corner unit that has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf. This is a rare opportunity as unique buildings like this are few and far between. It could be the ideal place to call home or as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.

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

Listing Agent: Shellie Young, Pa (941-713-5458)

Remarks: AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW ROOF • TURN-KEY FURNISHED Casa Bella is a spacious and beautifully updated 4-bedroom, 3-bath home offering more than 2,500 sq ft in the heart of Holmes Beach. Located just steps from shopping and dining and only a 5-MINUTE WALK TO BEACH, this property is situated in one of Anna Maria Island’s most desirable WEEKLY RENTAL ZONES, making it an excellent investment opportunity or a ready-to-enjoy personal beach retreat. This home has undergone extensive recent updates, including new wood flooring throughout, a brand-new spool (pool with spa jets), and a brand-new roof. Casa Bella is offered turn-key furnished, featuring a thoughtfully curated collection of artwork and unique furnishings. The coastal-style interior includes a large great room, fully stocked updated kitchen with custom cabinetry, stainless steel appliances, stone countertops, and a spacious dining area. The home comfortably accommodates up to 10 guests, with three bedrooms featuring king beds and a fourth bedroom designed with two twin-over-twin bunk sets—ideal for families or renters. Additional features include A LOWER LEVEL RECREATION ROOM with a ping-pong table, three updated bathrooms with spa-style finishes, 2 owner closets and three screened porch areas, perfect for enjoying morning coffee or evening breezes. Situated on a LARGE CORNER LOT with lush tropical landscaping, the outdoor area offers a private FENCED backyard oasis with ample space for dining, entertaining, and relaxing by the pool. Turn the key and start enjoying the ideal Holmes Beach lifestyle—whether as a personal coastal retreat or a strong VACATION RENTAL PERFORMER, Casa Bella offers flexibility, comfort, and an exceptional location.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Marlen Ryan (941-799-1046)

Remarks: OWNER VERY MOTIVATED !! West Bay Cove in Holmes Beach! This fully updated condo is being offered turnkey furnished, making it an ideal vacation getaway, income-producing rental, or full-time home in paradise.PICKLE BALL ! The bright corner layout offers open, inviting living spaces and a peaceful setting overlooking the pool, creating the perfect spot to unwind after a day at the beach. Thoughtful updates throughout give the home a fresh, coastal feel that’s ready to enjoy from day one. Westbay Cove is a beautifully maintained waterfront community on the Intracoastal Waterway with stunning Tampa Bay views, lush tropical landscaping, two heated pools, and tennis court. Just a couple of blocks to the beach and close to the trolley line, pier, local dining, and shopping—with convenient on and off island access. Don’t miss your chance to own a slice of Anna Maria Island.Walk to Publix, Shopping, Dining and the Gulf!

Listing is courtesy of: BOYD REALTY (941-750-8844)

Listing Agent: Brenda Boyd May (941-730-8589)

Remarks: Welcome to Southern Exposure! One of the best things about coming to sunny Florida from the cold North is a home with Southern Exposure so you can bask in the sun by this amazing pool all day long! Tranquil, private waterfront sanctuary — 624 Dundee on Key Royale is an impeccably renovated residence offering modern-luxe living by the water. This refined 3-bedroom, 2-bath pool home blends effortless flow with elevated finishes throughout. Meticulous landscaping and elegant paved walkways welcome you, while thoughtful attention to detail is evident in every room. Outdoors, a perfectly scaled heated pool and generous sun terraces are complemented by covered lounge space for sophisticated alfresco living and dining. A fully equipped dock with a 10,000 lb lift invites effortless access to open water, fishing, kayaking, or paddleboarding amid abundant coastal wildlife. Entertain beautifully: a sleek, brand-new kitchen with island opens to the dining area and elongated living room, creating seamless indoor-outdoor flow. The primary suite sits poolside with a private ensuite—ideal for morning swims or coffee on the lanai with sunshine all day! Two additional bedrooms share a well-appointed bath and can easily convert to a chic home office or guest quarters. Perfectly positioned on the island, this home captures the quintessential Anna Maria lifestyle—relaxation, sunlit days, and waterfront adventures—ready to be enjoyed as an exquisite primary residence or a sophisticated addition to your investment portfolio.

Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)

Listing Agent: Billi Gartman (941-545-8877)

Remarks: ~~~~~~~PRICE DROP~~~~~~~NOW is the time to buy this house. Make Anna Maria Island your own with a rare opportunity to own a truly iconic private island residence in Holmes Beach. Designed by celebrated architect Emily-Anne Smith, this distinctive home is recognized for its signature pink exterior, architectural integrity, and enduring coastal character. Set along a deep-water canal with direct access through Bimini Bay to Tampa Bay, the property offers seamless access to Florida waters for boating, sailing, and fishing. The setting feels intentionally residential and private, ideal for those seeking a refined second home or a full-time island residence designed for personal enjoyment rather than rental use. Offering nearly 2,800 square feet of interior living space and an additional 1,000 square feet under roof, the home provides generous proportions and thoughtful separation of spaces. A spacious screened porch overlooks protected mangroves, creating a naturally private backdrop and a peaceful connection to the island environment. Inside, soaring cathedral ceilings, custom millwork, and a classic Craftsman-style fireplace highlight the quality and intention behind the original design. The chef’s kitchen is outfitted with a 6-burner WOLF range, SUB-ZERO refrigerator, BOSCH dishwasher, granite countertops, and a vegetable sink, offering a well-appointed foundation for both everyday living and entertaining. The upper level features a versatile loft that includes a bedroom with ensuite bath, a recreation or lounge area, and a charming hidden treehouse retreat, adding character and flexibility to the home’s layout. The floor plan, construction quality, and architectural details provide an exceptional opportunity for a new owner to thoughtfully tailor the space to their own taste while preserving its timeless coastal appeal. With its architectural pedigree, deep-water boating access, and quiet residential setting, this home invites a new owner to build upon its legacy and create a personalized island retreat that will endure for years to come. Schedule your private showing and experience the setting, serenity, and potential that make this a truly special Florida retreat.

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

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

Remarks: This property is best suited for buyers seeking short-term rental income, a multi-unit investment, or a flexible owner-occupant strategy in a prime Holmes Beach location on Anna Maria Island. This income-producing triplex is located just steps from the Gulf beaches with no busy streets to cross and offers three separate rental units, including a 3-bedroom, 1-bath residence upstairs, plus a 2-bedroom, 1-bath unit and a studio apartment on the main level, allowing for multiple income streams, full-time investment use, or a live-in-one, rent-the-others approach. Currently operating as an active short-term rental, the property benefits from strong year-round demand driven by its proximity to the beach, dining, and entertainment near Bridge Street, as well as convenient access off the island via the Manatee Avenue Causeway. The central location also provides easy reach to IMG Academy, University Town Center, Lakewood Ranch, Downtown Sarasota, and both Sarasota-Bradenton International Airport and Tampa International Airport, making it attractive for owners, guests, and investors alike. Whether held as a turnkey short-term rental, positioned for a 1031 exchange, or used as a coastal residence with income, this Holmes Beach triplex offers a rare combination of location, flexibility, and proven rental performance.

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

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

Remarks: This property is best suited for buyers seeking short-term rental income, a flexible second home, or a long-term investment in a desirable Holmes Beach location on Anna Maria Island. This well-maintained duplex is ideally located near the island’s renowned Gulf beaches, dining, and shopping, with each side offering 2 bedrooms and 2 bathrooms designed for comfortable island living. Currently operating as an active short-term rental, the property provides immediate income potential while allowing personal use as desired, making it attractive to investors and vacation-home buyers alike. Both sides feature spacious private backyards with room to enhance outdoor living and the potential to add a pool (subject to city approval), offering additional upside in both enjoyment and rental performance. With its proven rental history, flexible use options, and sought-after island setting, this duplex presents a compelling opportunity to own income-producing property on Anna Maria Island.

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

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

Remarks: Newly renovated - Stunning 4-bedroom, 6.5-bath is perfect for beach lovers just a block from the Gulf of Mexico beaches. This island home features a backyard with a private pool and tiki bar, hot tub, BBQ area, covered patio with a foosball table, and a rooftop deck with water views. The main living space, includes a kitchen with a beautiful backsplash and quartz countertops, solid wood cabinets, island seating, couches, and a bright dining room with access to a covered deck overlooking the pool. The third floor hosts the primary bedroom, a private balcony with rooftop deck access, and an ensuite bathroom with a double vanity and a large shower. Outdoor amenities also include a pool, spa, This home is just a quick walk to the beach, and guests can easily take the trolley to Pine Ave for local delicacies, fish at the historic AMI city pier, or kayak in the bay waters.

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

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

Remarks: Under contract-accepting backup offers. Right in the heart of Holmes Beach, this 3-bed, 2.5-bath condo/townhouse is the perfect mix of vacation vibes and smart investment. Just a quick stroll to the sugar-sand beach, with the free trolley stop practically next door. You're steps from great shops, restaurants, and that classic laid-back island feel. Inside it's bright and open with a calm coastal look. Neutral floors and paint. Handy 10x14 bonus room downstairs for an office, gym, or games, plus oversized owner storage so you can lock away your stuff if renting. Owners have poured love into it lately: new 2025 roof, hurricane-rated garage door (garage freshly painted, smooth ceiling, new blinds), new furniture in the living areas, new oven, ~2-year-old dishwasher, fresh curtains/blinds/rod setups, and an enlarged screened porch with new furniture. Outside you've got two big balconies, a private ground deck, four new Adirondack chairs + tables, a grill, plus extras like 2 new bikes, beach chairs, wagon, sun tent, and a pickleball set—ready for island adventures. Fully furnished and turnkey, weekly rentals allowed year-round.

Listing is courtesy of: BOYD REALTY (941-750-8844)

Listing Agent: Brenda Boyd May (941-730-8589)