Refine Search
Map
Sort by
520 72nd Street, Holmes Beach
$2,950,000
3 Beds ⋅ 3 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code
The Epitome of Relaxed Elegance on Anna Maria Island. Lovingly cared for and beautifully renovated in 2024, this tropical waterfront retreat blends sophisticated design with the timeless charm of coastal living in a quiet neighborhood setting. Thoughtfully appointed with upscale furnishings and refined finishes, the home exudes understated luxury and effortless island elegance. This spacious three-bedroom residence is among the largest of its kind in Holmes Beach, offering 2,647 sq ft under roof and a large 11,115 sq ft lot. The generous open floor plan features two distinct living areas, and offers flexibility for entertaining, gathering with family and friends, or simply relaxing in your own private retreat. Beautiful interiors easily flow into tropical outdoor living spaces with lush landscaping and a beautiful heated pool / waterfall, creating a tranquil, secluded island oasis. Other key features include all hurricane windows and doors, a complete plumbing repipe, gas fireplace, tropical outdoor shower, kayak storage, all new appliances, and Garrison flood gates. For boating enthusiasts, the waterfront setting is a true highlight. Enjoy deep-water canal access to the Intracoastal Waterway, 68 foot dock with electric and water, a boat lift, and a convenient fish-cleaning station. Whether heading out for a day on the water, exploring the surrounding waterways, watching manatees and dophins, kayaking, paddleboarding, or enjoying an evening sunset cruise, the island lifestyle is right at your doorstep. Feel like enjoying the island? Travel a few short blocks to Anna Maria's sandy white beaches, gourmet restaurants, stunning sunsets, and coastal shopping. Elegant yet inviting, sophisticated yet relaxed, this beautifully maintained home offers a wonderful opportunity to experience the very best of Anna Maria Island living, where coastal charm, exceptional boating, and everyday comfort come together. Click on the link for a revealing virtual tour then call for your private showing today!

520 72nd Street, Holmes Beach
4307 Gulf Drive Unit 206, Holmes Beach
$535,000
2 Beds ⋅ 2 Baths ⋅ Cayman Cay Villas Condominium SubDv. ⋅ 34217 Zip Code
Welcome to Cayman Cay, where your island getaway awaits just steps from the sugar sands and turquoise waters of the Gulf! Ideally located directly across from Manatee Public Beach, this charming coastal community offers the perfect combination of beachside living, convenience, and investment potential. With a newly updated rental policy allowing weekly rentals as of March 2026, this is an exciting opportunity to own an affordable investment property on Anna Maria Island! An attached rental projection estimates over $53,000 in annual gross rental income, making this an attractive option for buyers looking to enjoy their own slice of paradise while generating rental income when they are away. This turnkey furnished 2-bedroom, 2-bath condo is ready for you and your guests to start enjoying island life immediately! The beautifully updated kitchen opens to a comfortable living and dining area, with sliding doors leading to a screened lanai where you can unwind and take in the colorful evening skies. The spacious primary suite features an ensuite bath and an additional storage closet that can be locked to securely store personal belongings between rental stays. The guest bedroom is thoughtfully furnished with two twin-over-full bunk beds, offering plenty of sleeping space for family and friends, while the guest bathroom features a convenient tub/shower combination. An in-unit washer and dryer adds to the comfort and convenience of this coastal retreat. Cayman Cay offers a relaxed, resort-style atmosphere with a heated community pool, inviting gathering spaces, BBQ grilling area, and shuffleboard courts. Step across the street to spend your days on the beautiful Gulf beaches, enjoy breathtaking sunsets, or explore the nearby restaurants and shopping. The free island trolley stops curbside, making it easy to discover all of Anna Maria Island without ever getting in your car! Whether you are searching for a personal beach retreat, an income-producing vacation rental, or the best of both worlds, this beautifully furnished condo offers an exceptional opportunity to embrace the island lifestyle. Pack your bags, bring your flip-flops, and start living your Anna Maria Island dream!

4307 Gulf Drive Unit 206, Holmes Beach
504 69th Street, Holmes Beach
$1,395,000
3 Beds ⋅ 2 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code
Island living, made easy. This ground-level Anna Maria Island home is fully renovated and comes turnkey furnished, just a few short blocks from the sugar-sand beaches and the island’s sunsets. Beautifully renovated in 2025 with a fresh modern design, the nearly 2,000 square foot home includes three bedrooms, two baths and new tile flooring throughout, with an ensuite bath in the primary bedroom. The new kitchen has custom cabinetry and all new appliances (2025), and both bathrooms have been redone with custom vanities, tile and contemporary finishes. The big-ticket items are already handled, including a new A/C (2025), a tankless water heater (2023) and hurricane impact windows (2023), and the laundry room has a washer, dryer, utility sink and plenty of extra storage. Outside, you’ll find a heated saltwater pool with a new pool heater (2025), landscaping, landscape lighting, irrigation, plenty of sunny yard space and a tiki-covered pergola, plus a 10x12 storage shed. Furniture and décor are included. Call to schedule your private showing.

504 69th Street, Holmes Beach
528 Key Royale Drive, Holmes Beach
$2,650,000
4 Beds ⋅ 4 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code
This is the kind of Florida home that changes the rhythm of everyday life—mornings overlooking the canal, afternoons cruising the Gulf, and evenings entertaining beside the pool beneath swaying palms. Set within the highly desirable waterfront community of Key Royale, this completely renovated 4-bedroom, 4-bath canal-front residence blends relaxed coastal living with striking modern design and exceptional boating access. Inside, soaring ceilings, clerestory windows, expansive glass, and wide-plank wood-look flooring create a light, open atmosphere that feels effortlessly sophisticated. The redesigned kitchen makes a sleek architectural statement with glossy contemporary cabinetry, quartz surfaces, a generous island, stainless steel appliances, an induction cooktop, designer lighting, and a dramatic slab backsplash. Open living and entertaining spaces flow naturally together, complemented by a custom wet bar and seamless access to the home’s outdoor retreats. The primary suite captures peaceful canal and tropical views through oversized windows and sliding glass doors. Its spa-inspired bathroom is a true showpiece, featuring a skylight, freestanding soaking tub, oversized glass-enclosed shower, sculptural floating vanity, warm wood accents, and elegant brass fixtures. Three additional bedrooms and beautifully updated bathrooms provide stylish accommodations for family and guests. Above the garage, the private fourth bedroom features its own entrance and balconies, creating an ideal guest suite, multigenerational retreat, home office, studio, or flexible bonus space. Outdoors, the home feels like a private island resort. Lush tropical landscaping surrounds an inviting pool and expansive brick-paver deck, while the covered screened lanai offers a shaded setting for dining, lounging, and entertaining. Beyond the pool, a manicured canal-side lawn leads to the seawall and private boat lift, placing boating, fishing, paddleboarding, and Gulf adventures directly outside your door. Thoughtful improvements include a new roof, four new air-conditioning systems, updated landscaping, a new garage door, and refreshed garage flooring. A distinctive benefit exclusive to this street, the property’s irrigation is supplied by a private well rather than metered city water, offering the potential for significant ongoing water savings. A brand-new well pump and irrigation system have also been installed, providing added efficiency and peace of mind. The vibrant coastal exterior, brick-paver driveway, mature palms, and layered tropical gardens create memorable curb appeal from the moment you arrive. Ideally positioned near Anna Maria Island’s renowned beaches, waterfront restaurants, local boutiques, and laid-back island attractions, this move-in-ready Key Royale waterfront home offers far more than a beautiful place to live—it offers the freedom to embrace the Florida boating lifestyle every day.

528 Key Royale Drive, Holmes Beach
215 67th Street Unit 6, Holmes Beach
$895,000
2 Beds ⋅ 2 Baths ⋅ The Blue Lagoon SubDv. ⋅ 34217 Zip Code
Resort-style, maintenance-free living awaits just steps from the beach on Anna Maria Island, where this beautifully renovated residence offers the perfect blend of luxury, privacy, and effortless coastal living. Set within an intimate community of only six residences, this exceptional 2-bedroom, 2-bath ground-floor retreat showcases charming Key West-inspired architecture by Emily Anne Smith and stands out with its own private tropical courtyard. Inside, the home feels bright, open, and beautifully finished, with vaulted ceilings, crown molding, designer light fixtures, stylish furnishings, and an easy-flowing floor plan designed for both everyday living and entertaining. The beautifully updated kitchen features crisp white cabinetry, quartz countertops, stainless steel appliances, and a generous breakfast bar that opens to the main living space, creating a natural gathering place for family and guests. Both bathrooms have also been thoughtfully renovated with quartz countertops and fresh, upscale finishes that continue the home’s polished coastal aesthetic. Offered turnkey furnished, every detail has been considered so you can begin enjoying the island lifestyle from the moment you arrive. The private outdoor spaces are equally special, with lush tropical landscaping, a peaceful courtyard, private lanai, and outdoor shower creating your own secluded island oasis. Just outside your door, enjoy resort-style amenities including a lagoon-style pool with a waterfall and a tiki hut, all shared by only six residences for a quiet and relaxed atmosphere. Ownership is designed to be easy, so you can spend more time enjoying the island and less time worrying about upkeep. Weekly rentals are permitted, and the property has a successful history as a vacation rental, offering excellent flexibility for personal use, investment, or both. The community is also pet friendly. The location is everything. Anna Maria Island is loved for its sugar-sand beaches, turquoise Gulf waters, unforgettable sunsets, charming shops, locally owned restaurants, and laid-back Old Florida character. With the beach just steps away, morning walks, sunset swims, paddleboarding, beach days, and evenings by the Gulf can become part of everyday life. Whether you are searching for a full-time island residence, seasonal escape, or proven vacation rental, this property offers an exceptional combination of location, privacy, convenience, style, and lifestyle. Ground-floor living, beautifully renovated interiors, private tropical outdoor space, resort-style amenities, turnkey furnishings, weekly rental flexibility, and incredible proximity to the beach make this one of the most desirable opportunities in this charming boutique community.

215 67th Street Unit 6, Holmes Beach
303 58th Street, Holmes Beach
$2,199,000
4 Beds ⋅ 3 Baths ⋅ Tidewater Preserve SubDv. ⋅ 34217 Zip Code
AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW METAL ROOF 9/2026• 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.

303 58th Street, Holmes Beach
106 81st Street, Holmes Beach
$5,250,000
4 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
One of the most distinctive residences on Anna Maria Island, this exceptional coastal home is a true celebration of thoughtful design, effortless entertaining, and spectacular Gulf views. Just steps from the shoreline and the island’s world-renowned beaches, this four-bedroom retreat was designed as a private haven for family and guests, with every detail carefully considered. An established and successful vacation rental, the property grosses over $350,000 annually, offering an exceptional opportunity for both personal enjoyment and investment. Three expansive travertine terraces create extraordinary outdoor living spaces, each offering its own unique setting. The second-level covered terrace features a fully equipped summer kitchen with grill, sink, and ice machine, overlooking the large heated pool and spa. The third-level terrace is open to the sky and furnished with a fire pit, creating the perfect place to gather while taking in unobstructed views of the Gulf of Mexico. Above it all, the rooftop terrace offers breathtaking panoramic views stretching from the Gulf to the Skyway Bridge. Every level is easily accessible by elevator or stairs. Designed for both luxury and efficiency, the home features more than 9,000 watts of solar power, offering exceptional performance with low-maintenance coastal living. The ground level includes two garages—one oversized two-car garage and a separate garage ideal for a golf cart, beach equipment, water toys, or owner storage. The second level showcases an inviting living and great room, dining area, and gourmet kitchen, with French doors opening directly to the covered terrace and summer kitchen. The kitchen is appointed with state-of-the-art appliances and a wine cooler, perfectly suited for both intimate gatherings and larger-scale entertaining. The thoughtfully designed bedroom layout offers four private en-suite retreats. Two are located on the second level alongside an office/media room, while the third level features the home’s expansive primary suite and an additional guest suite. From its exceptional outdoor living spaces and sweeping Gulf views to its sophisticated interiors, impressive energy features, and proven rental history, this extraordinary Anna Maria Island residence offers a rare opportunity to experience island living at its finest.

106 81st Street, Holmes Beach
600 Manatee Avenue Unit 226, Holmes Beach
$369,000
1 Beds ⋅ 1 Baths ⋅ Westbay Cove SubDv. ⋅ 34217 Zip Code
Turnkey Furnished 1-Bedroom Condo Just a Short Walk to the Beach on Anna Maria Island Enjoy the laid-back Anna Maria Island lifestyle from this elevated, turnkey furnished 1-bedroom, 1-bath condo in the desirable Westbay Cove community. Ideally located just a short walk from the public beach and within easy walking distance of local shops, restaurants, and island favorites. The free Anna Maria Island Trolley is also nearby, providing convenient transportation from the north end of the island all the way to Coquina Beach. This spacious second-floor condo features an open floor plan, abundant natural light, and a private balcony overlooking the pool and lush tropical landscaping. Built-in bunk beds provide additional sleeping space, making the condo especially convenient for visiting family, guests, or grandchildren. Offered fully furnished and move-in ready, the condo includes flat-screen TVs in both the living room and bedroom. Westbay Cove offers a fantastic collection of amenities, including two heated swimming pools, tennis and pickleball courts, outdoor gathering areas, a kayak and paddleboard launch, and beautifully maintained tropical grounds. Large dogs are welcome, adding even more flexibility for owners and guests. *Note: Property Information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyers' agent.

600 Manatee Avenue Unit 226, Holmes Beach
239 S Harbor Drive, Holmes Beach
$3,200,000
4 Beds ⋅ 6 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code
Welcome to Sea Glass Harbor, an exceptional expression of luxury coastal living in the heart of Anna Maria Island! Built in 2021, this exquisite multi-level residence offers 4 bedrooms, 5.5 baths, a private pool and spa, plus a versatile den/flex space—beautifully designed for refined island living, effortless entertaining, and unforgettable escapes. The main living level showcases an impressive open-concept kitchen, dining, and living area filled with natural light and an inviting coastal ambiance. The upscale kitchen is beautifully appointed with solid wood cabinetry, elegant quartz countertops, stainless steel appliances, and a generous center island that creates the perfect setting for entertaining family and guests. This level also offers two generously sized bedrooms, 2.5 beautifully designed baths with distinctive finishes, and a conveniently located laundry area. The upper level is home to a luxurious primary suite with a private ensuite bath, along with an additional spacious bedroom featuring its own ensuite. The bonus den/flex space provides even more options for your family to spread out and enjoy all of the areas of this stunning beach home. Designed to embrace the quintessential island lifestyle, the outdoor spaces are equally impressive. Relax beside the private pool and spa, entertain beneath multiple decks, or unwind in the lush tropical backyard. At the crown of the home, the rooftop deck delivers sweeping bay views—the perfect backdrop for sunset cocktails or quiet evenings under the stars. The unique split two-car garages provide exceptional parking and storage. Offered turnkey furnished with beautiful coastal décor, this remarkable residence is a successful vacation rental and presents a rare opportunity to own a luxurious island retreat with proven investment appeal. Ideally located in central Holmes Beach, you’re just minutes from the beach, exceptional local dining, shopping, and island entertainment. Boaters will appreciate convenient access to the community boat ramp, providing an effortless gateway to the surrounding waterways. Elegant coastal design, exceptional outdoor living, proven rental appeal, and an enviable island location—this is Anna Maria Island luxury at its finest!

239 S Harbor Drive, Holmes Beach
140 50th Street, Holmes Beach
$1,794,000
3 Beds ⋅ 2 Baths ⋅ Jones Sub SubDv. ⋅ 34217 Zip Code
Welcome to your island paradise, just steps from the sugary white sands of Manatee Beach, where gentle Gulf breezes and the laid-back Anna Maria Island lifestyle await. This beautifully maintained elevated concrete block home offers the perfect blend of coastal elegance, modern updates, and exceptional investment potential. The home is situated on an oversized corner lot, providing privacy and peaceful outdoor living. Featuring 3 bedrooms, 2 bathrooms, and a private elevator, this spacious home is designed for both comfortable everyday living and effortless vacation enjoyment. The open-concept floor plan is filled with natural light and centers around a large kitchen island, perfectly positioned beneath an oversized window overlooking the sparkling pool and rear deck—ideal for entertaining family and friends or enjoying an alfresco meal! The generous primary suite is a true retreat, offering a huge walk-in closet and a luxurious ensuite bath complete with a relaxing Jacuzzi soaking tub. Step outside to your private tropical oasis featuring a newly resurfaced (2022) heated saltwater pool and spa, surrounded by an elegant brick paver deck and professionally landscaped grounds. Enjoy morning coffee on the new front deck (2022) or unwind on the spacious rear deck while soaking in the peaceful island atmosphere and enjoying endless sunsets. The oversized lower level provides incredible flexibility with ample space for a home gym, game room, workshop, or additional storage. A large driveway and covered carports provide abundant parking for family and guests. Major updates include a durable metal roof installed in 2020 offering peace of mind for years to come. Inside features tray ceilings, crown molding, updated lighting and fresh paint in beachy neutral tones. Located in one of Anna Maria Island's most desirable areas, you'll love being able to stroll to Manatee Beach, restaurants, boutiques, and local entertainment. Hop aboard the free island trolley and explore everything the island has to offer—from historic Pine Avenue to Bridge Street and breathtaking Gulf sunsets. With weekly rentals permitted, this property offers outstanding flexibility as a full-time residence, vacation getaway, or income-producing investment, allowing rental income to help offset ownership expenses. Whether you're searching for your dream beach home or an exceptional island investment, this coastal retreat truly offers the best of Anna Maria Island living.

140 50th Street, Holmes Beach
203 72nd Street, Holmes Beach
$2,395,000
4 Beds ⋅ 4 Baths ⋅ West Wind Shores SubDv. ⋅ 34217 Zip Code
Welcome to Tidal Daze, a beautifully designed, turnkey furnished coastal sanctuary poised just a short stroll from the sugar-sand shores of Holmes Beach—where turquoise water, gentle Gulf breezes, and legendary sunsets become part of your everyday rhythm. A proven vacation rental with an established income history, this exceptional 4BD/3.5BA residence offers a rare balance of refined style, easy comfort, and lasting investment value. Sunlight pours through walls of windows and a central skylight, washing the open gathering spaces in a bright, airy glow that carries throughout the home. The graceful floor plan unfolds into both a welcoming family room and a separate living room—generous room to entertain, unwind, and settle in after a barefoot day by the water. The kitchen flows seamlessly into the main living areas, while an expansive wrap-around porch invites slow morning coffee, alfresco dining, and golden evening sunsets framed by lush tropical landscaping. Beyond the doors, a private backyard is composed for effortless island living: a sparkling pool, a covered entertaining area, and low-maintenance grounds that give you back your time for the Florida lifestyle. Ample driveway parking welcomes family and guests with ease, while a durable metal roof lends enduring value and coastal character. Best of all, the beach is close enough to leave the car behind—slip on your sandals, wander to the shoreline in minutes, and let sunrise walks and toes-in-the-sand afternoons unfold whenever the mood strikes. Whether you envision a primary residence, a serene second home, or a proven income-producing retreat, Tidal Daze presents an extraordinary opportunity in one of Anna Maria Island's most coveted enclaves—moments from the beach, celebrated dining, boutique shopping, and all the magic of island life.

203 72nd Street, Holmes Beach
522 68th Street, Holmes Beach
$2,995,000
4 Beds ⋅ 4 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code
Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold partially furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality.

522 68th Street, Holmes Beach
5701 Carissa Street, Holmes Beach
$3,295,000
5 Beds ⋅ 4 Baths ⋅ Holmes Gulf To Bay Dev Subdivison SubDv. ⋅ 34217 Zip Code
Tucked away in a quiet area of the island in a lush, tropical setting just moments from the beach, this beautiful 5BD/4BA residence captures the essence of coastal living with effortless style and thoughtful functionality, offering an exceptional opportunity in a desirable weekly rental zone. Framed by swaying palms and vibrant landscaping, the home welcomes you into a light-filled interior where a spacious living room with soaring ceilings, elegant plantation shutters, and a cozy gas fireplace creates an inviting space to gather and unwind. The open flow continues into a well appointed kitchen equipped with everything the family chef could want including a dining nook, but that family chef will love the scullery area with an additional stove and dishwasher for all the family gatherings. The scullery opens to the exterior where the outdoor grill and pizza oven are right at your finger tips. Two ensuite bedrooms, including a serene primary suite, offer comfort and privacy, while the remaining spacious bedrooms provide generous accommodations for the whole family. Step outside to a private pool area designed for soaking up the Florida sunshine, featuring a pool chiller for year-round comfort and surrounded by ample space for lounging and entertaining, along with two convenient outdoor showers. Practical features abound with natural gas service, a whole house generator, a durable metal roof, impact windows and more. There is also an exterior storage shed for all the beach toys, and abundant parking including two circular driveways on this corner lot. Located in the heart of Holmes Beach this location can’t be beat with a short walk to local shops, eateries and most importantly the sugar white sand and turquoise gulf waters.

5701 Carissa Street, Holmes Beach
600 Manatee Avenue Unit 116, Holmes Beach
$439,000
2 Beds ⋅ 2 Baths ⋅ Westbay Cove SubDv. ⋅ 34217 Zip Code
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!

600 Manatee Avenue Unit 116, Holmes Beach
5803 De Palmas Avenue, Holmes Beach
$1,075,000
3 Beds ⋅ 2 Baths ⋅ Neptunes Gardens SubDv. ⋅ 34217 Zip Code
Virtually Staged. This 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your personal styling! Bring your coastal creativity and create the perfect décor for you! You will love the ease of relaxing in your open family room and cooking in your updated kitchen with breakfast bar! With 3 bedrooms and a split floor plan, you have room for guests while enjoying the privacy of your own en suite. Make this your full time island escape or enjoy the benefit of income from the short term rentals that are allowed on this quiet street just steps to the soft sand of the Gulf beach! Bring your decorator spirit and make your island dream a reality by making this one your own!

5803 De Palmas Avenue, Holmes Beach
6006 Gulf Drive Unit 214, Holmes Beach
$749,900
2 Beds ⋅ 2 Baths ⋅ Playa Encantada Condominium SubDv. ⋅ 34217 Zip Code
Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.

6006 Gulf Drive Unit 214, Holmes Beach
314 61st Street, Holmes Beach
$2,150,000
5 Beds ⋅ 4 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Discover a versatile two-unit property in Holmes Beach offering the flexibility many buyers seek on Anna Maria Island. With a combined total of 5 bedrooms and 4 bathrooms, this property includes two fully turnkey residences: Pool Party South, a 3-bedroom, 2-bath main home, and Pool Party North, a 2-bedroom, 2-bath secondary unit. This configuration is well suited for those looking for a two-unit island home, a vacation property with short-term rental potential, or a second home that can help offset expenses when not in use. Both units feature coastal-inspired updates, including modern tile flooring, granite countertops, stainless steel appliances, newer roofs, and comfortable furnishings. Offered turnkey, the property is ready for immediate enjoyment or rental use. Weekly rentals are permitted, providing owners the flexibility to enjoy the island on their own schedule while generating income when away—an important consideration for buyers seeking short-term rental options on Anna Maria Island. The outdoor living area enhances the relaxed Florida lifestyle with a heated pool and spa, outdoor bar with sink, and multiple areas for dining and lounging. The oversized lot adds a sense of privacy, creating an inviting retreat for both owners and guests. This layout appeals to a variety of uses, including a multi-residence setup, a dual-unit investment property, or a home offering separation between living space and guest accommodations while maintaining rental flexibility. Located just a short walk to the Gulf beaches, as well as nearby dining, shopping, and island amenities, this property captures the ease and charm of Holmes Beach living. For buyers searching for an updated two-unit home with a pool, walkable beach access, and strong rental potential, Pool Party South and Pool Party North provide a compelling blend of lifestyle and opportunity on Anna Maria Island.

314 61st Street, Holmes Beach
511 Bayview Drive, Holmes Beach
$4,995,000
4 Beds ⋅ 5 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code
Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!

511 Bayview Drive, Holmes Beach
6400 Flotilla Drive Unit 15, Holmes Beach
$499,000
2 Beds ⋅ 2 Baths ⋅ Westbay Point SubDv. ⋅ 34217 Zip Code
Located in Westbay Point & Moorings on ANNA MARIA ISLAND, FULLY FURNISHED 2 bed 2 bath, 1 MILE from the BEACH. Front entrance opens into the shady SCREENED-IN LANAI, LAUNDRY is to the left with stackable WASHER/DRYER. Convenient STORAGE CLOSET/WORKSHOP to the right. Kitchen has a large pass through opening to the dinning room. Home provides a spacious living/dinning room combo. Both primary and guest bedrooms enjoy an en suite bathroom with tub/shower combo and abundant closet space. Enjoy the GLASSED IN FLORIDA ROOM or open the sliding glass doors to feel the breeze. RECENT UPDATES: ROOF, HVAC, WATER HEATER, and CARPET. Remote controlled ELECTRONIC HURRICANE SHUTTERS for extra protection. NEVER FLOODED, in FLOOD ZONE X. Located in WESTBAY POINT & MOORINGS, a waterfront community situated on a quiet bayfront setting on Anna Maria Island. 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. CONDO FEE INCLUDES: cable tv, high-speed internet, water, sewer, trash, ground maintenance, exterior maintenance, master insurance, pool, spa and more. Just a short 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. CONDO FEE INCLUDES: water, sewer, trash, cable, internet, pest control, pool and amenities. Enjoy ANNA MARIA ISLAND and a cozy atmosphere with local bike shop, restaurants, shopping options, and multiple access points to the beach.

6400 Flotilla Drive Unit 15, Holmes Beach
207 Peacock Lane, Holmes Beach
$1,600,000
3 Beds ⋅ 3 Baths ⋅ Aufra Sub Replat SubDv. ⋅ 34217 Zip Code
This completely updated Anna Maria Island 3 bedroom 2.5 Bathroom pool home is situated on a cul-de-sac, and features hurricane-rated windows, metal roof, concrete block construction and garage. Property is in a Weekly rental zone with a successful rental history, making this BEAUTIFUL BEACH HOME a perfect investment property, or family get away. Just 3 short blocks to the white sandy beaches of the GULF OF MEXICO and walkable to restaurants, establishments offering live music and charming shops making driving optional once you arrive! The kitchen and great room features an entire wall of sliding doors opening to the sunny south-facing outdoor living space and heated pool. The Master Retreat also opens to the pool area and features a master bath with walk-in shower, dual sink vanity and walk-in closet. A second Master suite and an additional 3rd bedroom with custom built in bunks make this gorgeous home spacious and functional for your family to comfortably relax both indoors and out. New Kitchen, new appliances, new bathroom vanities, new light fixtures, new pool equipment… and situated on an oversized lot, with an oasis backyard surrounded by tropical landscaping, paver decking, and a heated pool. Home is being sold TURN KEY FURNISHED with decorator finishes! This one won't last!

207 Peacock Lane, Holmes Beach
212 72nd, Holmes Beach
$2,985,000
4 Beds ⋅ 7 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
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. PROJECTED INCOME OF 175K.

212 72nd, Holmes Beach
506 69th Street, Holmes Beach
$1,095,000
2 Beds ⋅ 2 Baths ⋅ Bay Palms Add SubDv. ⋅ 34217 Zip Code
This beautifully updated 2 bedroom, 2 bath pool home offers comfort, flexibility, and exceptional value in the heart of Holmes Beach, featuring a spacious bonus room that can easily function as a third bedroom, office, game room, bunk room, or creative space tailored to your needs. Now offered at a newly improved price, this property presents an exciting opportunity to own a versatile island retreat just minutes from the beach. Wrapped in mature tropical landscaping, the private backyard oasis is designed for both relaxation and entertaining, complete with a heated pool, outdoor shower, firepit area, and multiple shaded lounging spaces perfect for unwinding after a day in the sun. Inside, the open concept layout enhances the flow between living and dining areas, with pocket sliders that open fully to the spacious rear porch, creating seamless indoor and outdoor living. The fully remodeled kitchen is a true highlight, showcasing crisp white cabinetry, sleek countertops, stainless steel appliances, and a generous island ideal for gathering. The primary suite offers a peaceful escape with a well appointed ensuite bath featuring a walk in shower, double vanity, and accessible design. Additional features include a one car garage with a freshly coated floor. Located just a short golf cart ride from the beach, shopping, and dining, this move in ready home delivers easygoing island living with the flexibility today’s buyers are looking for.

506 69th Street, Holmes Beach

How much is your home worth?

Get instant property value now!