Anna Maria FL Real Estate & Homes for Sale

Welcome to Palm Paradise, an exceptional opportunity to own in the coveted 100 block of Palm Avenue. Nestled in the heart of Anna Maria Island, this rare offering combines an unbeatable location with a spacious lot and flexible layout, making it ideal as-is or a canvas for your elevated dream home.This charming ground-level coastal retreat features four bedrooms and four bathrooms, thoughtfully designed for both comfort and privacy. The open-concept living space boasts a well-equipped kitchen with island seating, a generous dining area, and seamless flow to the screened lanai and tropical outdoor oasis. Step outside to your private heated pool, surrounded by lush landscaping and multiple lounge areas for soaking in the Florida sunshine.The primary suite offers a peaceful escape with a walk-in closet and ensuite bath, while each additional bedroom provides ample space for family. A full laundry room and multiple storage areas add convenience for everyday living or extended stays.Whether you're seeking a laid-back island home, a lucrative investment, or the perfect spot to build new, just steps from the beach, this is your chance to secure one of the most desirable addresses on the island. With no streets to cross to the Gulf, walkability to shops and dining on Pine Avenue, and access to the free island trolley, the location truly cannot be beat. While the original home was built in 1963, the home was renovated in 2013.Schedule your private showing today and experience life on Palm Avenue"where timeless charm meets endless potential.

Your BEACH HOUSE awaits, welcome to "AMI Breeze" on Anna Maria Island! This ELEVATED POOL HOME has 2 Bedrooms and 2 Baths along with your own tropical backyard oasis. Located in the heart of the North end in the highly sought after city of Anna Maria, this coastal charmer is just steps to the bay and Pine Avenue. It offers an open living/dining/kitchen area with beautiful vaulted wood ceilings that give the main living space a cottage feel and has plenty of windows to let the Florida sunshine in from the front porch. Open the french doors to the front balcony and sit out on the hanging porch swing and enjoy morning coffee and countless bay and gulf breezes. This home has a fully equipped kitchen with lots of cabinet space, stainless steel appliances, and a center island with quartz counters. The laundry room and pantry are just off the kitchen. The spacious primary includes an updated private ensuite bath, a walk-in closet and its own balcony with stairs down to the gorgeous pool. A game room area with a bar and mini fridge is on the lower pool level with the garage. Speaking of pool...one of the best features about this property is the extra-large 7,500 sq ft. lot & backyard which includes a lovely sizable, heated pool and spa with waterfall, a paved walkway and sundeck, mature landscaping, outdoor shower for sandy toes, and a covered patio! Anna Maria's pristine Gulf beaches are only a short walk away, the beautiful bay, pier and shops are at the end of the street and the General Store on Pine Ave is only one block over. Just pack your bags, it comes completely turnkey furnished with good rental history and zoned for weekly rentals. Another added bonus is that it is an approved Bert Harris home, if you choose to add two additional bedrooms later, your occupancy can be up to 10 guests giving this gem extra future revenue or additional space for your family. AMI Breeze won't last long - call to schedule your showing today!

Nestled on Anna Maria Island's most famous street, this beautifully renovated coastal retreat boasts five spacious bedrooms and four luxurious bathrooms, offering the perfect blend of comfort and style. Designed for seamless indoor-outdoor living, it features multiple porches where you can bask in the island breeze. Expansive sliding doors open to a generous deck, creating a natural flow between the elegant interiors and the lush tropical surroundings. Step down to the heated pool and spa, enveloped by vibrant landscaping, providing a secluded sanctuary for relaxation and entertainment. A private elevator enhances convenience, providing effortless access to all levels of the home and ensuring a seamless living experience. While the home's prime location places you just steps from the beach, renowned as the best surfing spot on the island, it offers an ideal setting for surfers drawn to its incredible waves. With premier shopping and dining just minutes away, you'll have the best of island living right at your fingertips.

Welcome to your dream coastal retreat! This fully furnished, elevated 2 bedroom, 1 bathroom home is perfectly nestled in the heart of Anna Maria Island. This stunning property is situated on a beautifully landscaped lot surrounded by lush tropical landscaping, a sparkling pool and spa. You can entertain in style with the outdoor kitchen and tiki hut bar area, or relax under the covered lanai with ceiling fans and seating. Step inside to discover a bright, open-concept living space adorned with coastal dcor and modern finishes. The living room features light-toned tile flooring, neutral paint, and a feature wall with a sleek electric fireplace, offering a cozy, yet contemporary vibe. The well-equipped kitchen features granite countertops, stainless steel appliances, and a glass-tile backsplash for a polished look. The dining space is perfect for entertaining and intimate gatherings with friends and family.The two spacious bedrooms provide ample closet space and natural light, while the updated bathroom offers a clean and functional layout with elegant finishes. Additional features include a two car garage, upper-level porch, and a bonus room downstairs, providing ample space for relaxation or hosting guests.With the close proximity to the pristine beaches, charming shops, local restaurants and recreational activities, Anna Maria Island offers something for everyone. Whether you're looking for a personal escape, vacation rental, or investment property, this beachside gem is an incredible opportunity.

Opportunity awaits on the coveted north end of Anna Maria Island. Embrace the allure of Anna Maria Island's coveted north end with this elevated 4-bedroom, 3-bath home offering views of the Skyway Bridge. Nestled in a prime short-term rental area, this property boasts a beautiful pool added in 2020, perfect for soaking up the Florida sun. With 1,932 sq ft of living space and situated on a 5,000 sq ft lot, the possibilities are endless. With a two-car garage and ample space for entertaining, this property is a blank canvas ready for your vision. Don't miss your chance to invest in one of Anna Maria's most sought-after locations. This home is being sold AS IS, presenting a rare opportunity to design your dream coastal retreat.

CUSTOM BUILT HOME IS CENTRALLY LOCATED IN Anna Maria 2 BLOCKS TO THE BEACH AND ONLY A BLOCK AWAY FROM ALL THE SHOPS AND RESTAURANTS ON PINE AVE. THIS HOME WAS BUILT WITH ALL THE HOME WAS BUILT WITH ALL HIGH END FINISHES INCLUDING WOOD GRAIN TILE FLOORS, SOLID WOOD CABINETS, QUARTZ COUNTERTOPS, CUSTOM TRIM PACKAGE, VAULTED CEILINGS, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR. OUTSIDE THERE IS A LARGE HEATED POOL AND SPA WITH SUN SHELF, SURROUNDED BY TROPICAL LANDSAPING ARTIFICIAL TURF AND EVEN A PUTTING GREEN. THIS WILL MAKE THE PERFECT SECOND HOME ON Anna Maria Island WITH GREAT RENTAL POTENTIAL.

Welcome to "Beach Breeze", your dream getaway nestled in the heart of Anna Maria Island. This beautifully appointed 4-bedroom, 3-bathroom coastal retreat offers the perfect blend of modern comfort and island charm, just steps from the sugar-white sands and turquoise waters of the Gulf with a short stroll to Pine Ave. Inside you will find a spacious, light-filled layout designed for relaxation and entertaining. The open concept living area features coastal decor and a fully equipped kitchen with stainless steel appliances and quartz countertops. The primary bedroom with an en-suite bath has direct access to the pool, while the additional bedrooms offer plenty of space for family and guests. Step outside to your private tropical oasis with a wood deck, heated pool and spa with sun loungers. Whether you are sipping morning coffee or enjoying sunset strolls to the beach, or enjoying Anna Maria Island's vibrant shops and restaurants, Beach Breeze is the perfect place to unwind and make unforgettable memories. Already a successful rental, Beach Breeze will make a great investment property or family getaway for years to come.

Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable streets on Anna Maria Island. SeaLuxe is a home thats perfectly positioned to put you just a short walk away from a world-renowned beach or to Pine Ave where you can find locally owned shops and restaurants. This coastal retreat features 3,265 sqft of indoor living space, 4-bedrooms all with ensuite bathrooms, and 2 powder baths. Once inside, you are welcomed by an open concept living space bathed in natural light, featuring high ceilings and a seamless flow between spaces. The gourmet kitchen is a chef's dream with form and function, equipped with premium stainless-steel appliances, walk in pantry, quartz countertops, solid wood cabinetry, and a large island with seating. The spacious primary bedroom offers a serene retreat with a luxurious ensuite bath featuring a soaking tub, walk-in shower, and a generous walk-in closet. Take the elevator to the top floor where you will find an inviting movie room equipped with a wet bar and beverage fridge, a powder bath, and one of the four bedrooms. On the ground level of this luxurious property, you have an area that is designed for ultimate relaxation and entertainment, featuring a stylish entertainment room with a pool table for indoor fun. Step outside to a resort-style outdoor space complete with a gorgeous pool, spa, and sun shelf, all surrounded by lush landscaping and a beautifully turfed area. An expansive covered patio offers the perfect setting for al fresco dining and grilling, making it easy to unwind or entertain in true island style. SeaLuxe perfectly blends sophisticated coastal design with exceptional comfort, offering not just a luxurious escape but a highly successful, turnkey vacation rental investment with future reservations in place. Schedule your private showing today and see why so many guests fall in love with this home!

THIS INCREDIBLE CUSTOM BUILT ESTATE IS JUST FIVE HOUSES FROM THE GULF AND NESTLED ON ONE OF THE MOST COVETED STREETS ON ANNA MARIA ISLAND!!! LOCATED WEST OF GULF DRIVE YOU ARE JUST STEPS FROM THE SUGAR-WHITE SANDS AND TURQUOISE WATERS! This beautifully designed coastal home offers over 2,600 square feet of light-filled living space and is currently operating as a successful vacation rental, making it ideal as both a private retreat and an income-producing investment. THIS HOME HAD NO WATER INSTRUSION WITH THE HURRICANES. With five spacious bedrooms and four and a half bathrooms, the home provides comfort, style, and flexibility for families or guests seeking the best of island living. Step inside to an airy, open-concept great room where soaring ceilings, detailed window trim, and tile floors set the tone for relaxed sophistication. The spacious living area flows into the dining space and a chef's kitchen complete with stainless steel appliances, dual ovens, and a large island accented by custom cabinetry. A dedicated laundry room and thoughtful layout throughout ensure everyday comfort and convenience. This home's exterior is just as impressive, featuring a metal roof, a charming double-door entry, a two-car garage, and a paver driveway lined with tropical landscaping. Multiple balconies invite you to enjoy ocean breezes, morning coffee, or peaceful evening sunsets. Out back, your private oasis awaits, with a covered outdoor living and dining space equipped with ceiling fans for year-round enjoyment. The heated saltwater pool with a sun shelf and built-in hot tub is perfect for cooling off after a beach day or entertaining under the stars. Living on Anna Maria Island means embracing a laid-back, coastal lifestyle that's truly one of a kind. Explore miles of pristine beaches, stroll or bike to charming shops and locally owned restaurants, catch a sunset at Bean Point, or fish off the beach. With no high-rises and a strong sense of community, Anna Maria offers a timeless Old Florida feel, where golf carts are the norm and every day feels like vacation. Whether you're searching for a full-time residence, a seasonal getaway, or a high-performing rental property, this exceptional home captures the essence of island life in one of the most treasured spots on Florida's Gulf Coast.

MODERN COASTAL MASTERPIECE WITH SWEEPING VIEWS OF TAMPA BAY!! THIS ANNA MARIA ISLAND HOME OFFERS 4 BEDROOM 4.5 BATHS WITH A ROOFTOP DECK AND HEATED POOL!!! Welcome to Three Fifteen, perfectly situated on one of the most coveted locations. With views of Tampa Bay, this luxury pool home is the epitome of sleek design and beachside elegance, offering the ultimate indoor-outdoor lifestyle. This show-stopping residence features multiple expansive decks, including a rooftop deck complete with a hot tub and panoramic bay views that stretch to the horizon. Whether you're sipping your morning coffee as the sun rises or entertaining guests under the stars, every level of this home brings the outdoors in. Step inside to a stunning open-concept great room with floor-to-ceiling sliders that frame the lush palms and sparkling water beyond. The kitchen is a true statement piece"navy shaker cabinetry, brass hardware, high-end appliances, and a waterfall quartz island with bold veining create an entertainer's dream. Each bedroom is designed as a tranquil retreat, including a custom bunk room built for fun and function. The spa-inspired bathrooms feature rich textures, luxury tilework, and stylish dual vanities. Out back, you'll find a private, resort-style heated pool and spa, surrounded by tropical landscaping and cozy covered lounges for year-round relaxation. And if that's not enough there is an elevator and a rooftop putting green which brings a playful, private amenity right to your doorstep. Anna Maria Island is a barrier island gem on Florida's Gulf Coast, known for its old Florida charm, sugar-white beaches, and laid-back luxury. Life here is slow-paced and sunshine-filled " a place where flip-flops are the dress code and golf carts are the preferred ride. Enjoy seven miles of pristine coastline, endless water sports, bike-friendly streets, and breathtaking sunsets that feel like a daily event. Locals and visitors love the quaint boutiques, art galleries, and family-owned restaurants sprinkled along Pine Avenue and Gulf Drive.Whether you're looking for a private island escape, a family-friendly investment property, or a place to live where every day feels like vacation, Anna Maria Island delivers lifestyle, beauty, and unmatched serenity. Home is currently a very successful vacation rental with forward bookings in place.

Welcome to your dream coastal getaway"this stunning 4-bedroom, 3-bath home is perfectly situated in one of the most sought-after neighborhoods near the North End of Anna Maria Island. Just steps from the serene bay beaches and moments to the iconic AMI City Pier and lively Pine Avenue, this beautifully refreshed island retreat is the ultimate blend of luxury, comfort, and charm.With coastal hues, this home radiates beachy elegance inside and out. Surrounded by swaying palms, you'll be greeted by two spacious balconies and a grand staircase leading to your main entrance. Inside, the open-concept living space is bright and inviting, featuring a cozy great room, large dining area, and a fully equipped kitchen bathed in natural sunlight"ideal for entertaining or unwinding after a day in the sun.With four beautifully appointed bedrooms, there's plenty of room for family and friends to relax and recharge. The upper-level primary suite is a true retreat with an ensuite bath showcasing a therapeutic jetted soaking tub and separate walk-in shower. A private rear porch off the main floor bedroom and kitchen connects to your tropical backyard oasis via a spiral staircase.Step outside and enjoy your private heated pool, surrounded by lush landscaping, lounging areas, and a built-in grill for evening cookouts and poolside dining. Additional highlights include an elevator shaft ready for installation, allowing easy access to all levels for you and your guests.Live the laid-back island lifestyle"grab a cruiser bike, hop on the free trolley, or take a leisurely walk to explore everything Anna Maria has to offer. From artisan shops and quaint cafs to world-renowned seafood spots and sunset cocktails on the beach, every day here feels like a vacation. Don't forget to make time for a peaceful stroll to Bean Point, where powdery sand and breathtaking sunsets await.

Island Living at Its Finest!Welcome to your private slice of paradise on Anna Maria Island"where every day feels like a vacation. Nestled just two blocks from vibrant Pine Avenue and a short stroll to the pristine Gulf beaches and AMI City Pier, this idyllic, island-inspired retreat offers the perfect blend of laid-back luxury and tropical tranquility.Surrounded by lush, manicured landscaping, this 3-bedroom, 2.5-bath multi-level home exudes coastal charm. Step through the bright French door entry and instantly feel the warmth of bamboo wood floors and natural light dancing through every room.Upstairs, the spacious main living area is thoughtfully designed with an open concept that seamlessly connects the living room, dining space, and modern kitchen. Entertain effortlessly or relax in the inviting great room, complete with access to a screened-in lanai that overlooks your very own tropical backyard oasis. The kitchen features sleek granite countertops, stainless steel appliances, and custom cabinetry"perfect for preparing island-inspired meals or hosting family and friends.Start your mornings with coffee and ocean breezes on the lanai, and wind down in the serene primary suite, complete with dual vanities, a spa-like glass shower, and a step-up Roman tub for soaking the stress away. Upstairs, two additional bedrooms and a shared full bath provide a peaceful retreat for guests, along with a second balcony to enjoy the view.Outside, your private heated saltwater pool is the ultimate island escape. Add a few lounge chairs and fire up the grill in the dedicated outdoor entertaining area"ideal for weekend barbecues, happy hour with friends, or simply soaking up the Florida sun.Explore Pine Avenue's charming boutiques, grab gourmet doughnuts and fresh coffee from local favorites, or dine under the stars at local hotspots.Whether you're seeking a primary residence, a coastal second home, or a lucrative vacation rental, this property offers everything you need to live your best island life. Don't just visit paradise"own it.

Welcome to 803 Gladiolus St, A Bean Point Paradise, a tranquil oasis and serene retreat on Anna Maria Island. Just across the street from the renown beach of Bean Point, this stunning property offers one of the largest parcels on the island with a lush tropical backyard featuring a shimmering pool and soothing spa, perfect for relaxing. Whether you seek a full-time residence, a second home, or a vacation rental, this property meets all needs with a Burt Harris Settlement agreement allowing occupancy for up to 12 guests.Property Overview:Bedrooms/Bathrooms:5 bedrooms, 4.5 bathroomsParking:Accommodates up to 6 vehiclesLocation:Just a five-minute stroll to the pristine Gulf beaches at Bean Point.Parking: the property has parking for 8 cars outside and 4 cars in the garage, a key feature in one of the most deaired location on the island with limited parking.Condition:The entire home was renovated in the last 4 years with new hurricane, salt resistant roof, hurricane resistant exterior, decks and ceilings, new bathrooms, floors, kitchen and paint.Outdoor Enjoyment:Embrace island living with a private backyard oasis featuring a pool, spa, BBQ grill, and poolside refrigerator for al fresco dining. Enjoy close proximity to the beach, and explore nearby shops and restaurants for the ultimate outdoor lifestyle.Interior Features:Step inside to an inviting, completely renovated interior where a spacious living area designed for entertaining large groups with ample seating awaits, centered around a generously-sized couch. The chef's kitchen boasts sleek stainless steel appliances, a kitchen island, and a formal dining table. The home offers both indoor and outdoor dining options. The property also has an elevator and central vacuum system.The second floor houses three bedrooms, while the primary suite and an additional bedroom are on the third floor. A cozy den/Game room features a queen sleeper sofa for extra guests. Enjoy peaceful escapes on balconies accessible from the living room and primary bedroom, perfect for morning coffee or evening relaxation.Additional Amenities:The converted garage is now a game room, complete with a ping pong table, foosball, comfy couch, and TV"ideal for unwinding after a beach day.Rental Income: The property has been one of most coveted properties on the Island due to its location and amenities with a strong, lucrative history or rental income and lots of satisfied and returning renters.803 Gladiolus St seamlessly combines luxury and comfort in an idyllic setting, serving as your gateway to paradise living on Anna Maria Island's Bean Point. Don't miss the opportunity to own one of the most

EXCEPTIONAL COASTAL LIVING AT IT'S FINEST!!! ONE HOUSE TO THE BEACH ON ONE OF THE MOST COVETED STREETS ON ANNA MARIA ISLAND!!! Welcome to 103 Park Avenue, a timeless retreat designed by the renowned EMILY ANNE SMITH. Just steps away from the breathtaking shores of the Gulf and walking distance to the vibrant charm of Pine Avenue, this residence offers the best of island living.Crafted with impeccable attention to detail and made for entertaining, this remarkable property features 4,540 square feet of beautifully curated living space. From the moment you enter, you're welcomed into a spacious living room with a cozy fireplace and seamless access to a breezy front verandah"perfect for gathering with friends and family. Additional fireplaces warm both the great room and the luxurious primary suite. The chef's kitchen is nothing short of spectacular, outfitted with marble countertops and backsplash, custom cabinetry, top-of-the-line appliances, two dishwashers, a butler's pantry, and dual sinks"ideal for everything from everyday meals to entertaining on a grand scale. As with all of Emily Anne Smith's architectural gems, this home is filled with inspired touches and thoughtful design that must be experienced to be fully appreciated. These one-of-a-kind properties rarely come to market and are beloved for their character, craftsmanship, and enduring style. The estate includes both a main residence and a private guest cottage, offering flexible space across 5 bedrooms, 4.5 baths, three spacious verandahs, two private offices, and a stunning outdoor oasis complete with a pool and outdoor shower. The separate cottage is perfect for guests or family. Additional features include peekaboo Gulf views. Home is currently a very successful vacation rental. Built prior to current city restrictions and protected under the Bert Harris Act, this property presents a rare and valuable opportunity"whether you're searching for a full-time island home, vacation getaway, or high-end investment property. Just a short stroll away from the charm of Pine Ave, where boutique shops, art galleries, and cozy cafes await, this home also offers effortless access to the island's free trolley system, award-winning beaches, and renowned waterfront dining- capturing the very best of the Anna Maria Island lifestyle!Don't miss this chance to own a true piece of Anna Maria's architectural history"just steps from the sand and surf.

Introducing a brand-new architectural marvel"a fully furnished, 6-bedroom, 7-bathroom deep-water canal-front estate nestled just two blocks from the beautiful sands of Anna Maria Island. This stunning residence is more than just a home"it's a lifestyle statement, a private resort, and a legacy investment wrapped in one unforgettable package.Expertly crafted with full concrete block construction from top to bottom, this home is engineered to last, featuring hurricane impact-rated windows, doors, and a Cat 5-rated roof"offering the ultimate in durability, security, and peace of mind. Whether you're seeking a luxurious year-round residence or an elite income-producing property, this home delivers on every level.Step inside and prepare to be captivated. The interiors are a masterclass in modern coastal design"refined yet approachable, luxurious yet relaxed. Soaring ceilings, walls of glass, and curated designer lighting flood the home with natural light, creating an atmosphere of serene grandeur. At the heart of the home lies a gourmet chef's kitchen that rivals any culinary magazine spread: custom cabinetry, dramatic quartz countertops, a striking concrete range hood for architectural drama, a full Sub-Zero appliance suite, and a hidden walk-in Butler's pantry that adds elegance and function behind the scenes.Every room in the house has been thoughtfully curated"from the expansive open-concept living and dining areas to the multiple covered balconies and loggias that seamlessly blend indoor-outdoor living. The primary suite is a private sanctuary with a spa-inspired bathroom, walk-in closet, and balcony overlooking the water.The expansive rooftop deck is a true crown jewel"an entertainer's dream and a private escape all in one. Thoughtfully designed for both grand gatherings and quiet reflection, this oversized outdoor space offers ample room for al fresco dining, cocktail parties under the stars, or simply soaking in panoramic views of the island, canal, and golden Gulf sunsets. Outfitted with multiple seating and lounge areas, it's the perfect perch to unwind after a day on the water or host unforgettable evenings high above it all.And speaking of water"the backyard is nothing short of a tropical resort-style oasis. A shimmering pool and spa are framed by lush palms and generous lounging areas, while the deep-water canal offers a direct, bridge-free route to the open Gulf of Mexico"ideal for boating enthusiasts looking to hop aboard from the comfort of their private dock.This home is being offered fully turnkey furnished, professionally designed and appointed with luxury pieces throughout"allowing you to begin enjoying it immediately, or to start generating income from premium short-term rentals. With the ability to rent weekly, and demand for high-end vacation homes on Anna Maria Island at an all-time high, this property presents both a one-of-a-kind lifestyle and an exceptional investment opportunity. The photos, while breathtaking, can't convey the full experience of walking through this home. To understand its craftsmanship, scale, and sheer beauty, a private tour is essential. Don't miss your opportunity to claim this crown jewel of Anna Maria Island. Schedule your exclusive showing today.

Completed in December 2023, welcome to Boundless Waves - an exceptional coastal retreat in the heart of Anna Maria Island.This stunning 6-bedroom, 6.5-bath luxury residence is being offered fully turnkey furnished, ready for you or your guests to settle in and start enjoying island life immediately. Designed with effortless elegance and comfort in mind, the home features lush tropical landscaping, a+private heated pool, & SPA and an expansive rooftop deck with sweeping views of Anna Maria Island Gulf and Bay both. Large 3+ car garage and game room.Step inside to discover a bright, open-concept floor plan with custom contemporary finishes throughout. The main living level showcases a designer kitchen equipped with sleek stainless steel appliances, a statement island, and plenty of room for entertaining. The dining area and great room flow seamlessly onto a spacious covered deck, inviting the outdoors in and filling the home with natural light.Also on the main floor, you'll find a convenient half bath, a laundry room, two guest suites with private baths, and a serene primary suite complete with French doors leading to a private deck.Upstairs offers even more flexibility with a den/lounge area, a full guest bath, two additional guest suites, and a luxurious second primary suite featuring a spa-style shower and a generous walk-in closet.The crown jewel? A rooftop deck where you can soak in panoramic island views and breathtaking sunsets " the perfect way to begin and end each day.Located just moments from Anna Maria's charming shops, top-rated dining, and pristine beaches, this home is ideally positioned for both personal enjoyment and investment. With a 3-night minimum rental policy, Boundless Waves has strong rental income while offering maximum flexibility for owners and guests alike.

It's time to be ON POINT! Welcome to a relaxing vacation rental home called ON POINT! A great home, in a great location, in a great city on an AMAZING island. On Point is a 4 bedroom, 3 bathroom home at the north end of Anna Maria Island. Steps to Bay Front park and a very short walk to the beach of the Gulf of Mexico where you and your guests can bask in the sunshine, build sand castles, watch some of the best sunsets in the world and take a walk in the sugary soft sand. This home has 3 bedrooms and 2 bathrooms on the second floor and all the extras are on the ground floor. It's got that OLD FLORIDA FEEL with so much new to bring it to life. With plenty of room for the family and your guests on the inside, but just as much outside around the heated pool. Perfect for hanging out, grilling and chilling. There is a perfect little sitting room off the pool along with a bathroom for convince as you are cooling off with a cocktail from the days worth of sunshine on the beach. Loaded with games for fun and close to so much of what the city of Anna Maria is all about. Restaurants, shopping, exploring and just being an Islander. It's one of the best places to get your feet wet in the Island market. Continue its success as a short term rental or simply keep all to yourself and live the Anna Maria Life of a getaway in paradise. Come see your new home in one of the most coveted places on earth.

Opportunity knocks at Anna Maria Island's much desired North End. This 3 bedroom/2 bath home, although damaged in Hurricane Helene, is structurally sound and situated in an ideal location on a quiet street on a 7,784 square foot lot - within easy walking distance to the sugar sand Gulf Beaches and the shops and restaurants that define Pine Avenue. The drywall has been cut back and has been remediated. The home features a large great room, split floor plan, interior laundry, impact windows, artificial turf, large work shop and a one car garage. A perfect chance to own a piece of the Island and make it your own.

ARE YOU READY FOR THIS?! This GROUND level home did not get any water or flood during the hurricanes! Not even in the pool! Now is your chance to own WEST of Gulf Drive on Anna Maria Island! They don't come up often- only 5 houses to the Gulf!! This quaint and cozy beach cottage is 2 bedrooms, 3 full baths, formal living room, great room AND fully enclosed and under air lanai. SO much living space to hang and relax! Stay cool under the covered patio in the shade on hot summer days and a large outdoor shower to rinse off from the beach. Enjoy the private back yard with lush landscaping, heated salt water pool, sun shelf, paver deck and spa with specialty lights! Owners did many upgrades in 2022-2024 which include the pool, electrical, AC, water heater, 3rd bathroom, new roof, hurricane shutter on front (remote controlled) and all impact windows and doors! This is the perfect opportunity to own your little slice of paradise on Anna Maria Island!

Enjoy the finest in Anna Maria lifestyle at Still Waters Beach House. This beautifully designed and decorated 6 bedroom house is an excellent Island estate. Whether you are looking to reconnect with family or friends, or just escape the world in the Old Florida lifestyle, Still Waters Beach House is the perfect place to enjoy Anna Maria Island. Recently updated with a full kitchen remodel with stainless steel appliances and a sit in counter space. All three levels of exterior deck including the rooftop balcony is new, new pool and spa equipment, and updated interior furnishings! Relax in the open living room, with beautiful hardwood floors/tile and island inspired decor. What better way to enjoy the outdoors in privacy than the pool, grotto, and hot tub, surrounded by tropical landscaping. Enjoy a sunset toast and views of Tampa Bay from the rooftop deck or from one of the many balconies. Fun game room/Pool room with foosball and indoor putt-putt. Take a short stroll to the heart of the shopping district on Anna Maria's historic Pine Avenue or the beaches of the Gulf. Still Waters Beach House is sold turnkey furnished and move in ready. Great investment property especially being 6 bedrooms, Bert Harris approved for 14 guests and rental numbers in 2023 it did over $278K!

You have to see this home to appreciate the efficient layout and spacious living spaces. This property comes turnkey furnished, making it a seamless transition for the fortunate new owners. Meticulously maintained and never rented, the home exudes a sense of care and pride. For those considering short-term rentals, this residence presents an attractive opportunity. Featuring three bedrooms, including two master suites, and three bathrooms, the open floor plan enhances the spacious and airy ambiance, creating an inviting atmosphere for residents and guests alike. Nestled along a serene saltwater canal, this home caters to boating and fishing enthusiasts with a 12,000lb boat lift and a fish cleaning station. This deepwater canal has no fixed bridges to get to open water, both sailboats and power boats are welcome. The screened covered back porch overlooks the canal, providing a tranquil setting for relaxation and entertainment. Immerse yourself in the refreshing saltwater pool. The pool is heated with an electric heat pump and comes with a pool sweep and fitted cover.Inside, the residence boasts high-end finishes, including granite countertops, crown molding, Hunter Douglas window dressing and hardwood floors throughout, with tile accents in the bathrooms.Practical features of this elevated home include a new metal roof and a completely enclosed lower level that boasts a 2-car garage, ample storage space under the entire home on a generous lot with 75' on the canal, ensuring privacy and room for outdoor activities.A short seven-block stroll or bike ride takes you to the beautiful Gulf beaches that Anna Maria Island is renowned for. And Tampa Bay water access is literally half a block away, across South Bay Blvd. Again, turnkey furnished and ready to move in. Never any water intrusion in living space.

Located in the "heart" of Anna Maria City, sits this ground level, 3 bedroom, 2 bath home just waiting for you! It has been updated and features bright Caribbean colors and new furnishings. The master bedroom and 2nd bedroom both accommodate queen beds, while the 3rd bedroom has two sets of bunk beds. It is conveniently located near restaurants, shopping, the ice cream shop, Pine Ave AND is only a short walk to the gulf beaches. There is a huge backyard with a covered patio to relax and have your morning coffee. There is plenty of room to add a pool. Currently a vacation rental, rental allows 1-7 days and would be a great investment! Schedule your showing today!

Location, location, location! Just steps from world-famous Bean Point and breathtaking sunsets, Absolutely Anna is a stunning 2-bedroom, 2-bathroom retreat in the heart of Anna Maria. Designed for seamless indoor-outdoor living, this home exudes coastal charm with an open floor plan and thoughtfully designed spaces.The bright and airy living area flows effortlessly into a well-equipped kitchen, ideal for entertaining. A large screened-in front porch invites you to relax and enjoy the gentle island breeze, while the expansive covered outdoor area offers a cabana-style setting perfect for year-round enjoyment.The primary suite is a private sanctuary, featuring an ensuite bath with double sinks, a walk-in shower, and a private balcony overlooking the pool. The second bedroom, complete with its own ensuite bath, opens onto the front screened-in porch, creating a tranquil retreat for guests.Whether you're lounging poolside, taking a short stroll to the beach, or embracing the island lifestyle, Absolutely Anna is the perfect getaway. With a strong rental history, this home offers an incredible opportunity as a personal retreat or investment property. Don't miss your chance to own a slice of paradise"schedule your showing today!

Welcome to Go With The Flow, a brand-new, luxurious five-bedroom, five-and-a-half-bath retreat that blends modern opulence with a vibrant beachside charm.Designed for ultimate relaxation and entertainment, this stunning property features an unparalleled Lazy River-style pool with an in-ground spa, offering the perfect setting to bask in the radiant Florida sunshine.Step inside to discover an immaculate chef's kitchen, fully equipped with high-end appliances and everything needed to craft gourmet meals. A sleek bar area with a wine fridge and an elegant formal dining space add to the home's sophisticated allure. The spacious living area invites you to unwind, with contemporary sofas, stylish side chairs, and a Smart TV for endless entertainment.Each guest room is a private oasis, thoughtfully designed with crisp linens, ample storage, and personal televisions. The primary suite is a sanctuary of luxury, featuring a king-sized bed, plush bedding, and an ensuite bathroom complete with a double vanity, soaking tub, and walk-in shower. Additional accommodations include three king guest suites, each with a private ensuite bath, and a bunk room designed for younger guests, also with its own ensuite. A washer and dryer add extra convenience for extended stays.Venture up to the rooftop deck and experience breathtaking views paired with unbeatable entertainment. With ample seating, a stylish bar area, and a versatile 3-in-1 game table, it's the perfect spot for unforgettable nights under the stars.Ideally situated in the heart of Anna Maria, this exquisite retreat is just a short stroll from the beach, charming local restaurants, boutique shops, and iconic destinations like Pine Avenue and the AMI City Pier.Escape to Go With The Flow for unforgettable beach days, endless relaxation, and memories to last a lifetime!

Welcome to Anna Maria Chateau, a beautifully renovated vacation rental nestled on a peaceful street at the serene northern tip of Anna Maria Island. Just a few blocks from the island's renowned beaches and Bean Point, this spacious 3-bedroom, 2-bathroom home offers the perfect blend of comfort and style, making it an ideal primary residence or lucrative vacation retreat.With vaulted ceilings in both the living area and bedrooms, the open and airy design creates an inviting atmosphere throughout. Custom craftsmanship is evident in every corner, from the elegant crown molding and custom wood trim to the hand-scraped hickory wood floors and tongue-and-groove ceilings and walls. The chef-inspired kitchen boasts custom cabinetry, a large island, sleek granite countertops, and top-of-the-line stainless steel appliances, making it an ideal space for entertaining.The home also features thoughtfully designed custom closet systems, energy-efficient LED lighting, and a convenient inside laundry room with a washer and dryer. The oversized upstairs deck overlooks the private pool and provides a perfect spot for relaxation. The heated swimming pool with a new pump and heater is a true highlight, complete with shallow sun shelves and in-water seating. Outdoor living is equally impressive, with multiple spaces designed for enjoyment, including a large granite bar, LED lighting, and beautiful wood ceilings. The fenced yard offers both privacy and ample space for outdoor activities. Whether you're hosting friends and family or enjoying quiet moments in your own retreat, the poolside recreation room offers a granite bar, dining area, game room, and shaded sitting areas, ensuring that your time outdoors is just as luxurious as the interior. Anna Maria Chateau is truly a gem, offering unmatched charm and modern convenience in one of Florida's most sought-after locations.Property generated over 150k in 2024 even with hurricane restricting rentals to 8 months. It is projected to generate 180k + for 2025