Location: Holmes Beach
Do Not Show Listings
4307 GULF DR #109, HOLMES BEACH, FL 34217
$469,000115 Days on yellowkey MLS ID: A4675685
5 Days Off yellowkey (back on 4/11/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1974Monthly Fee: $1,242 Tax: $2,866 (2025)Community: Cayman Cay VillasCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,866
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Steps from the Gulf and newly approved WEEKLY rental policy! Experience the best of Anna Maria Island in this charming, ground-level 2-bedroom, 2-bathroom condo located in a premier Holmes Beach community. This residence perfectly balances modern upgrades with the relaxed, "Old Florida" charm that makes this island world-famous. THE INTERIOR: The heart of this home is the newly remodeled kitchen, featuring crisp quartz countertops, contemporary cabinetry, high-end hardware, and a deep farm sink. Sold fully turnkey, the transition to your new beach life is seamless. OUTDOOR LIVING & PRIVACY: Relax and enjoy your morning coffee on your covered, screened-in lanai which overlooks the sparkling community pool or step out for effortless access to the heated swimming pool for a midday dip! For ultimate seclusion, the primary suite features a rare, private open-air patio. Complete with a private outdoor shower, it is a serene sanctuary perfect for sunbathing or getting lost in a good book COMMUNITY & LOCATION: Located directly across the street from the sugary sands of the Gulf of Mexico, this complex offers a true resort feel with a heated pool, BBQ grilling area, and shuffleboard courts. Whether you’re looking for a permanent residence, a seasonal getaway, or an investment, the flexible rental policy - WEEKLY RENTALS ALLOWED - offers great potential. HIGHLITES: • Prime Location: Easy walk to shopping, dining, and island entertainment, with quick access off-island. • Pet-Friendly: Owners are welcome to bring their pets! • Maintenance-Free: Ground-level entry with no stairs to navigate. ADDITIONAL OFFERINGS: covered parking, LG storage closet, small enclosed area off of BD #2 for office space or additional storage. Don't miss this opportunity to own a piece of paradise where the beach is your backyard and every day feels like a vacation!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Lindsey Strickland (941-737-3491)
504 58TH ST, HOLMES BEACH, FL 34217
$1,450,00039 Days on yellowkey MLS ID: A4685187
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1540 Built: 1962 Tax: $10,386 (2025)Community: Holmes Beach Fourteenth UnitSingle Family
Taxes:$10,386
Remarks: Recently renovated 3 bedroom, 2 bath canal front home on a beautiful, deep water, natural-lined mangrove canal with a boat dock. This meticulously cared for home is located on a very quiet street in Holmes Beach. A shady, private paver lined courtyard sits canal side and is a serene spot to escape. PGT Hurricane rated windows & doors installed Oct. 2021, new metal roof installed 2025, new A/C, ductwork & insulation 2025 and all new appliances 2025. Centrally located on the island just steps from Holmes Beach City Park & Public Event Venue, with pickleball courts, a dog park and The Island Library. Walking distance to great dining options & local shopping boutiques. Hop on your golf cart to enjoy the pristine beach & Gulf located just minutes from your door! One car garage and ample driveway parking. This great home is truly "island living" at its best.
Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)
Listing Agent: Marianne Norman-Ellis (941-685-3393)
215 67TH ST #6, HOLMES BEACH, FL 34217
$935,00012 Days on yellowkey MLS ID: A4688457
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1038 Built: 1971 Tax: $3,001 (2025)Community: The Blue LagoonCondo
Taxes:$3,001
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning Coastal Retreat – Blue Lagoon, North Holmes Beach Experience the ultimate Anna Maria Island lifestyle in this beautifully renovated 2BD/2BA ground-floor condo located in the charming Blue Lagoon community of only six residences. Just a short stroll from the powdery white sands and turquoise waters of the Gulf, this exceptional property offers the perfect blend of luxury, comfort, and island charm. This residence has been completely renovated from top to bottom, creating a stylish, move in ready coastal retreat. The open concept layout features quartz countertops, crown molding, high ceilings, luxury vinyl plank flooring throughout, stainless steel appliances, updated lighting and fixtures, fresh interior paint, and tasteful furnishings and décor designed to complement the relaxed island vibe. Step outside and enjoy one of the most inviting resort style pools on Anna Maria Island, complete with a stunning lagoon design, a dramatic 10ft waterfall, and a shaded tiki hut. Perfect for relaxing afternoons or gathering with friends and family. The only unit with a private lanai offers a tranquil spot for morning coffee, remote work, or evening cocktails after a day at the beach. Whether you're searching for a full-time island residence, luxurious second home, or high-demand investment property, this opportunity truly stands out. Weekly rentals are allowed and the complex is pet friendly, making it ideal for both personal enjoyment and rental potential. Live the island dream at Blue Lagoon where beach days, sunsets, and the best of Anna Maria Island are just steps away.
Listing Agent: Andrea Miller (860-541-1050)
6250 HOLMES BLVD #37, HOLMES BEACH, FL 34217
$850,00091 Days on yellowkey MLS ID: A4677811
REDUCED by $10,000 (1.2%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1536 Built: 1992Monthly Fee: $885 Tax: $4,005 (2025)Community: North Beach Village IiSpa: NoTownhouse
Taxes:$4,005
Remarks: Income Producing - Turnkey - Fully Furnished - Vacation Rental Property located in the desirable North Beach Village community. 3D tour showing 360 degree views of the home available for a virtual walkthrough. Start generating rental income from day one with this highly successful income property, with over $30,000 in bookings already for 2026 and almost $10K in 2027! Whether you’re searching for a full-time island residence, a seasonal getaway, or a proven income-producing property, this exceptional offering truly checks every box. Experience the best of Anna Maria Island living, where every day feels like a vacation. This property allows weekly rentals, 52 weeks a year, providing maximum flexibility and earning potential. Located in the desirable pet-friendly North Beach Village community—with no size or breed restrictions—residents and guests alike enjoy a relaxed coastal lifestyle, complete with a large community pool ideal for swimming laps or unwinding after a day at the beach. This beautifully decorated condo is nestled within a quiet community and is just a three-minute walk to the sugar-sand shoreline. Enjoy being moments away from charming local shops, popular island restaurants, and all the laid-back character Anna Maria Island is known for. Prefer to leave the car behind? The free island trolley stop nearby makes getting around effortless. Outdoor enthusiasts will appreciate nearby amenities including a dog park, playground, basketball courts, pickleball, and tennis courts, all just minutes away. Inside, this inviting island retreat offers 1,536 square feet of bright, open living space, featuring three bedrooms, two and a half bathrooms, and indoor laundry. Recent updates include a new roof (2025) and a standout primary bathroom unlike any other in the community. The spacious primary suite boasts a large walk-in shower with seating, dual-sink vanity, linen closet, and a private commode area, creating a true spa-like retreat. The home also features hurricane shutters and a hurricane-rated reinforced garage door, offering peace of mind for owners and guests alike. Neutral flooring and soothing paint tones throughout create a calm, coastal atmosphere that both owners and guests will love. Multiple outdoor living spaces enhance the island experience, including a screened-in porch tucked among the trees for added privacy, two large balconies, and a private ground-level deck—perfect for enjoying island breezes and outdoor dining. A large sleeper sofa allows plenty of room for extra guests. On the ground level, in addition to the main living area, you’ll find a generous 10' x 14' bonus space, ideal for a home office, gym, or game room. There is also an oversized 9'6" x 8' owner’s closet/storage room, providing the perfect place to securely store personal belongings while the property is rented. Offered fully furnished and truly turnkey, this exceptional property presents a rare opportunity to own a slice of paradise with outstanding income potential. Whether you’re investing, vacationing, or settling in year-round, this home delivers the ultimate island lifestyle—sun, sand, and serenity just steps from your door. Shared condominium expenses may result in lower overall carrying costs compared to some single-family homes.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kim Bowersox (407-383-3519)
511 BAYVIEW DR, HOLMES BEACH, FL 34217
$5,290,000103 Days on yellowkey MLS ID: A4675904
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3353 Built: 2020 Tax: $24,007 (2024)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$24,007
Tax Year: 2024
Remarks: 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!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
105 49TH ST, HOLMES BEACH, FL 34217
$3,750,00046 Days on yellowkey MLS ID: A4683981
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2999 Built: 1940 Tax: $41,424 (2024)Community: JonesSingle Family
Taxes:$41,424
Remarks: Beachfront Bliss – Gulf Views from Every Angle! Just one house from the beach, this 4-bedroom, 4-bath coastal stunner delivers postcard-perfect Gulf views straight from the kitchen sink—yes, you’ll actually smile while scrubbing plates! Natural light throughout, high ceilings, 2 sided fireplace, wet bar in the living room, open living area that flows into a chef’s kitchen. Stainless steel appliances, gas stove, double ovens and more! The coastal chic blue countertops and tile throughout for easy beach sand clean up! Step outside to your wrap around balcony to dine and enjoy the gulf breeze. Backyard features your private heated pool that includes a sun shelf. All the bedrooms are spacious and have their own privacy. The primary suite is upstairs with even better views of the Gulf to wake up to. Enjoy your private balcony AND a spiral staircase leading up to the roof top deck, ideal to watch sunsets and dolphins jump in the water. Master bathroom has a huge walk-in shower, soak in tub, dual sinks and a large walk-in closet that includes a safe. The location is central to the island, close to everything and very convenient. 30 day minimum rental period. One house away from the Gulf, this may be the island’s best-kept secret!
Listing Agent: Jason Sato (941-778-7200)
403 75TH ST, HOLMES BEACH, FL 34217
$2,485,000348 Days on yellowkey MLS ID: A4650766
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1655 Built: 1955 Tax: $17,404 (2024)Community: Bay Palms Add Fourth UnitSpa: YesSingle Family
Taxes:$17,404
Remarks: Charming Coastal Cottage in Holmes Beach. Welcome to this newly and meticulously remodeled coastal retreat, ideally located in the heart of Holmes Beach. This one-of-a-kind, artsy beach cottage blends timeless charm with modern elegance and smart technology. Step through the inviting rain glass double doors into a spacious open-concept living, dining, and kitchen area, where a dramatic lighted cupola and vaulted ceilings create a stunning first impression. A custom shell stone fireplace with a wood mantle adds warmth to the cozy seating area—perfect for relaxing or entertaining. The chef’s kitchen is a true showstopper, featuring an oversized, lighted quartz island with seating, beadboard cabinetry, and a custom wave-patterned glass backsplash. High-end appliances include an ILVE Majestic 4-burner gas stove with griddle, GE Café refrigerator, wine fridge, and porcelain farm sink—all designed with entertaining in mind.Craftsmanship continues throughout with custom millwork, shiplap accents, paneled walls, and solid-core doors. Oversized sliding glass doors open to reveal a tropical backyard oasis, complete with a free-form heated pool and spa, paver patio with artificial turf. The lush, mature landscaping with up lighting show off the tall palm trees, perfect for a evening cocktail party under the stars. The southern-facing yard is perfect for dining, lounging, and soaking up the sun. Each of the three bedrooms and 2.5 baths showcases custom chrome period fixtures, retro-inspired sinks, and designer details. Tech-savvy buyers will love the smart home features, including Lutron lighting controls, LED lighting, Sonos sound system, security cameras, and plantation shutters. The property includes a 250-gallon buried propane tank serving the on-demand water heater, gas grill, pool heater, and stove. It’s also generator-ready with existing plumbing and wiring in place. There is city dockage close by for boating enthusiast's This extraordinary home offers a rare blend of beachy charm and luxurious amenities—an absolute must-see!
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
408 71ST ST, HOLMES BEACH, FL 34217
$1,799,000181 Days on yellowkey MLS ID: A4668595
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2037 Built: 1966 Tax: $16,372 (2024)Community: Bay Palms AddSpa: NoSingle Family
Taxes:$16,372
Remarks: Welcome to paradise at Coco Cay! This beautiful 4 bedroom 4 bathroom home has been completely remodeled top to bottom. Brand new hurricane impact windows and doors, a new roof, kitchen, appliances, bathrooms, flooring, paint, furnishings, and even a new pool! This island oasis is move-in ready and only a few blocks from the world-famous beaches of Anna Maria Island. You will notice coastal décor as soon as you step into this island gem. The home provides a spacious open living area with teal accents, stainless-steel appliances, quartz countertops, and a game room conveniently adjacent to the kitchen with a pool table and dartboard. Outside you'll enjoy a screened in porch accessible from the living room, a seating area complete with a firepit, and a huge covered lanai for cooking and dining poolside. Weekly rentals are allowed. Make an appointment for your private showing and see what makes Coco Cay an excellent full-time home or investment property.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Don Purvis (901-240-2180)
130 50TH ST, HOLMES BEACH, FL 34217
$2,799,00049 Days on yellowkey MLS ID: A4683830
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2947 Built: 2010 Tax: $37,816 (2024)Community: The Villas On 50Th StreetSingle Family
Taxes:$37,816
Remarks: Own the sunset and step into a lifestyle buyers dream about—and renters actively seek out. Just moments from the Gulf, this stunning 6-bedroom, 4.5-bath coastal retreat delivers the perfect blend of luxury, comfort, and exceptional income potential. Designed to host and impress, the home lives like a private resort. Outside, guests are drawn to the resort-style pool with a sun shelf, a relaxing hot tub, and a tranquil waterfall feature. The outdoor bar and expansive patio create an effortless entertaining space, while the rooftop deck offers unforgettable Gulf-view sunsets that elevate every stay. Inside, the bright, open-concept design is made for connection, comfortably accommodating large groups, families, or vacation guests. High-end finishes meet relaxed coastal style, creating a space that feels both upscale and welcoming—exactly what today’s buyers and renters are looking for. Whether you're building a strong vacation rental portfolio or securing your own coastal escape, this property stands out as a high-demand, memory-making destination with proven appeal.
Listing Agent: Lisa Tucker (863-206-2938)
501 65TH ST, HOLMES BEACH, FL 34217
$1,750,00051 Days on yellowkey MLS ID: A4681843
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2208 Built: 1973 Tax: $8,263 (2024)Community: Holmes Beach 17Th UnitSingle Family
Taxes:$8,263
Remarks: **Seller is offering a $25,000 incentive for a contract closed before June 1st!** Discover a rare opportunity in Holmes Beach: a fully renovated four-bedroom, three-bathroom waterfront home offering immediate access to the Intracoastal Waterway and the Gulf of America, along with direct beach access just steps away. Every element of this property is brand new, creating a true turnkey residence equally suited for personal enjoyment or investment. Set on a deep-water canal with no bridges to open water, the home is designed for effortless boating. The composite dock and electric boat lift allow for quick departures to the Gulf, while the brand-new pool anchors a private outdoor setting ideal for entertaining or quiet relaxation. Whether returning from a day on the water or an afternoon at the beach 2 blocks away, the outdoor spaces are designed to complement the island lifestyle. Inside, the renovation reflects a clean, modern coastal design with thoughtful functionality throughout. Four spacious bedrooms and three beautifully appointed bathrooms provide flexibility for hosting family and guests. Upgrades such as instant hot water at every faucet and an EV-ready charging connection add everyday convenience, while the garage offers valuable storage (an increasingly important feature on Anna Maria Island) plus potential for a future ADU conversion (buyer to verify zoning, permits, and feasibility). Holmes Beach remains one of the most desirable enclaves on Anna Maria Island, known for its walkability, local dining, boutique shopping, and relaxed sophistication. With monthly rentals permitted, this home offers exceptional versatility as a primary residence, seasonal retreat, or income-producing property. Completely updated, impeccably located, and ready for immediate occupancy and with all furniture available for separate purchase, it represents island living at its finest.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Banning Tibbetts (941-713-5663)
3701 5TH AVE #1, HOLMES BEACH, FL 34217
$695,00018 Days on yellowkey MLS ID: A4686018
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1430 Built: 1982 Tax: $3,272 (2025)Community: Gulf View TwnhsSpa: NoCondo
Taxes:$3,272
Remarks: Gulf View Town Houses Condominium is one of a few select small association properties nestled just south of Manatee Public Beach. Just far enough away for a quiet beach day and just close enough to be an attractive location for vacation renters. A convenient grocery store and shopping district are just 1/8 mile east of this Holmes Beach condominium, making errands a breeze. The Association has been diligent and timely with their maintenance and repairs of the building and common elements, which are in tip top shape. Beach access is a short 150-yard walk west, offering the public beach restaurant and tiki bar just a short stroll north. This is one of the premier weekly rental locations in Holmes Beach and Anna Maria Island as a whole. Unit #1 has two designated parking spaces, a small first floor storage shed, and is one of just four units in this intimate single building condominium complex with heated pool on a spacious corner lot. West facing, with tons of light, this spacious two story 2 bed 2.5 bath condominium is the ultimate in hassle free island living for both owners and renters. On the first floor you will find tile floors throughout an open floor plan with an all-wood cabinet galley kitchen with induction cook top/range and hood, nice breakfast nook, and large living room with ½ bath. The kitchen also features full matching stainless GE Profile line appliances in great shape. A 5x12 ft balcony just off the living room is perfect for sunset viewing and windows and doors are hurricane rated and have been replaced in the past few years. Upstairs find the Primary en-suite bedroom with private west facing balcony and full tile bath with whirlpool tub and separate shower. The guest bedroom is also roomy with private full tile shower bathroom. The laundry room with washer and dryer are also found on the second floor. Definitely schedule a showing to take a closer look! Thanks *A FEW PHOTOS ARE VIRTUALLY STAGED*
Listing is courtesy of: ANNA MARIA ISLAND REAL ESTATE CORPORATION (941-504-7821)
Listing Agent: Bill Romberger (941-504-7821)
620 NORTH POINT DR, HOLMES BEACH, FL 34217
$2,200,000161 Days on yellowkey MLS ID: A4670040
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2570 Built: 1993Monthly Fee: $150 Tax: $16,646 (2025)Community: North Point Harbour Unit TwoSingle Family
Taxes:$16,646
Remarks: Hidden gem on North Point Drive in one of the most exclusive communities on Anna Maria Island. This beautifully remodeled 3 Bed, 3.5 Bath two story home is nestled on a quiet cul-de-sac, offering privacy and tranquility just steps away from the stunning waterfront. The bright and airy layout features vaulted ceiling in the living room and loft area, creating an inviting atmosphere for relaxation and entertainment. The gourmet kitchen, the heart of the home, boasts custom tile and solid wood cabinetry, marble backsplash, a six-burner gas range and an expansive island, perfect for culinary enthusiasts. Each bedroom is an ensuite with walk-in closets, offering privacy and comfort. The primary suite, located on the main level, features a luxurious walk-in shower, built -in medicine cabinets, laundry bin cabinetry, and a double sink vanity. There is a dedicated A/C system for each floor. Step outside to enjoy a large patio that leads to your private dock with a new 12,000 pound boat lift, making it easy to access the beautiful waters of Tampa Bay. Additional outdoor amenities include a kayak lift, fish cleaning station, outdoor shower and kayak storage rack. The property is surrounded by lush, tropical landscaping, enhancing its curb appeal and creating a serene environment. Additionally, a secure gated area for your pets ensures a safe space to play. Community amenities include access to a pool and tennis/racquetball courts, perfect for an active lifestyle. With an elevation of more than 8 feet above base flood elevation, your home is safe and secure, potentially qualifying for favorable flood insurance rates. Don't miss this rare opportunity to own a piece of paradise on Anna Maria Island! Schedule your private showing today.
603 EMERALD LN, HOLMES BEACH, FL 34217
$4,340,000336 Days on yellowkey MLS ID: A4652348
Bed: 5 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 3700 Built: 2024 Tax: $21,278 (2023)Community: Key Royale 11Th AddSpa: YesSingle Family
Taxes:$21,278
Tax Year: 2023
Remarks: Stunning turnkey new construction on Anna Maria Island, located on a serene and rare double channel lot in the Key Royale neighborhood. This spacious residence features 5 bedrooms, 2 on the main level and 3 upstairs, all with en suite and walk-in closets offering ample space for family and guests. The main floor’s primary suite includes a large bathroom with steam shower and beautiful marble tile flooring. Enjoy 2 living spaces, one on the main level and another with a large balcony overlooking the canal on the second floor. The elevator provides easy access to both levels. Convenient laundry with 4 washers and 4 dryers, 2 upstairs and 2 on the main level. Upgraded finishes throughout with wide plank engineered walnut flooring, marble tile in the bathrooms, quartz countertops, 8' high extra thick upgraded doors, and upgraded trim package. The modern kitchen boasts brand new high-end Sub-Zero and Wolf paneled appliances and upgraded cabinetry. Step outside to enjoy covered seating and dining areas, a large saltwater pool and spa with breathtaking canal views, and 2 new composite wood docks with new seawall on this home's rare corner channel access, ideal for water enthusiasts. The property also features garage spaces to accommodate 4 vehicles, and new mature landscaping. The home's interiors are thoughtfully designed with hand-curated, beach inspired furnishings which are included in the sale.
3100 GULF DR #2, HOLMES BEACH, FL 34217
$649,00014 Days on yellowkey MLS ID: TB8492057
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 884 Built: 1982 Tax: $2,969 (2025)Community: Island In The SunCondo
Taxes:$2,969
Remarks: Welcome to your income-producing slice of paradise in Holmes Beach! This 2-bedroom, 2-bathroom condo is perfectly positioned as a vacation rental, offering strong income potential in one of Florida’s most desirable beach destinations. Designed with both guests and owners in mind, the main living area is located on the first level and features an open-concept layout ideal for entertaining and relaxing after a day at the beach. The seamless flow between the living room, dining area, and kitchen creates an inviting space that renters love. A full bathroom on the main floor adds extra convenience for guests. Upstairs, two bedrooms and a full bathroom provide a private retreat, making the layout ideal for vacationers or families. The separation of living and sleeping spaces enhances guest experience—helping drive strong reviews and repeat bookings. Located just moments from the Gulf beaches, guests can easily enjoy the sand, clear waters, and unforgettable sunsets. Close proximity to local dining, shopping, and island attractions makes this property highly desirable year-round. NEW ROOF (2024), LVP FLOORING (2022), INTERIOR PAINT (2025), FRIDGE/DW/RANGE (2025), POOL REFINISH (2026)
Listing is courtesy of: KELLER WILLIAMS SOUTH TAMPA (813-875-3700)
Listing Agent: Jennifer Young (301-675-4601)
227 S HARBOR DR, HOLMES BEACH, FL 34217
$3,650,00035 Days on yellowkey MLS ID: A4684262
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3274 Built: 2023 Tax: $45,830 (2024)Community: Sportsmans Harbor RevSingle Family
Taxes:$45,830
Remarks: Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
414 79TH ST, HOLMES BEACH, FL 34217
$1,495,00092 Days on yellowkey MLS ID: A4677980
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1621 Built: 1968 Tax: $16,313 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$16,313
Remarks: Welcome to your own piece of paradise on Anna Maria Island! This is a BRAND NEW remodel including new metal roof, all new plumbing and electrical, pool/spa and turf and much more! This charming coastal home offers the perfect blend of comfort and island living. Nestled off a quiet street, this property is just a short stroll from the stunning Gulf of Mexico beaches. Featuring 3 bedrooms and 3 bathrooms, its spacious enough for family and guests. One bathroom having access right off the pool for easy access. The open concept living and dining area create an inviting space for relaxation and entertainment. The updated kitchen has modern appliances, quartz countertops and plenty of cabinet and storage space with a large island. Enjoy the Florida sunshine in your private backyard oasis, complete with new turf and a putting green, heated pool/spa and lush landscaping. Your garage provides ample storage space for your beach toys and outdoor gear. Holmes Beach is known for its serene atmosphere and friendly community. This is your chance to own a piece of paradise on Anna Maria Island. Whether you're looking for a permanent residence or a vacation retreat, weekly rentals allowed. Property owners in Holmes Beach can lease a boat slip from the city for $600/year! Schedule your private showing today.
5608 HOLMES BLVD, HOLMES BEACH, FL 34217
$1,050,000385 Days on yellowkey MLS ID: A4645925
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 2011 Tax: $14,104 (2024)Community: Barefoot BungalowsSingle Family
Taxes:$14,104
Remarks: Under contract-accepting backup offers. GREAT VACATION rental history with many repeat guests!!!!This charming 3 bedroom 2 bath pool home at the beach could be all yours. Nestled in the heart of Holmes Beach, where you can take a short stroll down Holmes Boulevard to city center where you will find adorable shops and restaurants where you can sit, sip, and dine and enjoy a real small town coastal experience. This lovely bungalow style home features a beautiful private pool with swim up table and a shallow sun deck , all brand new furniture, appliances, AC with an upgrade purification Air scrubber component by Aerus, kitchen counters and base cabinets and pool equipment. This home is very well received by its long standing repeat guests and decorated so adorable with its subtle soft coastal chic colors it is sure to please everyones need for the beach. It is very active and successful vacation rental with ample space for your family fun filled vacations, and when you are not using it yourself you can earn income to help offset the costs. Schedule your private showing. FYI this is a typical island "land condo" with NO HOA, each owner takes care of their own home, they do share the same landscaper by choice.
Listing Agent: Michelle Laade (941-737-9662)
311 59TH ST #B, HOLMES BEACH, FL 34217
$1,445,00062 Days on yellowkey MLS ID: A4682162
REDUCED by $15,000 (1.0%) on 04/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 2027 Tax: $1 (2025)Community: Holmes Beach 15Th UnitHalf Duplex
Taxes:$1
Remarks: Pre-Construction. To be built. 45% down, 10% at drywall, the rest not due until Certificate of Occupancy. A big splash for Green Street Builders into the Holmes Beach market. They bring 35+ years of experience, and refreshing coastal elegance at a more affordable price point. Not everyone has $10 million for a beach home, we think you'll like these offerings. This plan has 4 defined sleeping areas per side (including an open air loft), high-functionality, and open concept design with cathedral-like ceilings. Quartz waterfall counters, modern sleek cabinets, lots of glass. Same stuff everyone likes in new construction, just more obtainable. We step outside to the deck overlooking the pool area. Under-roof, a massive, shaded entertaining space. Room for Ping Pong, dining, other games, a great TV set up, lounging, or however you see it. It's a lush, tropical, vacation themed setting for you to enjoy... or for your guests to come back to year after year. See all bedrooms and living areas in attached floor plan.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Jason Skowronski (941-812-6090)
311 59TH ST #A, HOLMES BEACH, FL 34217
$1,395,00062 Days on yellowkey MLS ID: A4682143
REDUCED by $15,000 (1.1%) on 04/04/2026
114 78TH ST, HOLMES BEACH, FL 34217
$999,9007 Days on yellowkey MLS ID: A4688098
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1556 Built: 1947 Tax: $2,575 (2025)Community: Holmes Beach Dev 3Rd UnitSingle Family
Taxes:$2,575
Remarks: Prime Holmes Beach opportunity just steps to the beautiful beaches of Anna Maria Island. Located on a quiet street in one of Holmes Beaches most desirable areas, this property is all about location, flexibility, and future upside. The existing structure has been impacted by Hurricane Helene and is ready for its next chapter. For investors, builders, or end users looking to capitalize on a high-demand island market, this is a chance to secure a well-positioned parcel with strong long-term potential. Holmes Beach continues to see consistent demand driven by its walkability to the beach, access to dining and shopping, and its appeal as both a second-home and income-producing market. Whether your strategy is to renovate, reposition, or build new, the fundamentals here support the investment. Short distance to the Gulf, close to everything on the island, and situated in an area where quality properties continue to command attention—this is a strategic play in a market where opportunities like this are increasingly limited.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jeff Jordan (941-224-7657)
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