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$489,000
1 Beds ⋅ 1 Baths ⋅ Tradewinds Condo SubDv. ⋅ 34217 Zip Code
Experience the charm of Old Florida living just steps from the Gulf of Mexico at this beautifully renovated turnkey-furnished beach cottage in the sought-after Tradewinds Beach Resort on Anna Maria Island. Whether you're searching for a carefree island retreat, an income-producing vacation rental, or the perfect blend of both, this stylish one-bedroom residence offers exceptional flexibility with no minimum rental restrictions and professional on-site management available. Completely remodeled with a fresh coastal aesthetic, the interior is move-in ready, and designed for immediate enjoyment. Soft tropical hues, wood-look tile flooring, and an open floor plan create a bright, inviting atmosphere, while the updated kitchen showcases stone countertops, custom cabinetry, newer stainless steel appliances, and generous workspace. The beautifully renovated bath echoes the same timeless finishes, and in-residence washer/dryer provides added convenience. Offered turnkey furnished, the residence includes a king-size bed, queen sleeper sofa, two flat-screen televisions, and tasteful décor, allowing you to begin enjoying island life from day one. Outside, a shaded private front patio with a newly installed paver walkway provides the perfect setting for morning coffee or evening cocktails, while assigned parking is conveniently located just outside your door. Offering added peace of mind, the home has been thoughtfully updated with Hardie® siding, impact-rated windows and doors, and new plumbing and sewer lines. Tradewinds Beach Resort captures the relaxed character that has made Anna Maria Island one of Florida's most beloved destinations. Pastel-colored cottages draped in jasmine and bougainvillea line a quiet private lane leading to a heated bayside swimming pool, fishing pier, picnic pavilions, charcoal grills, and beautifully landscaped grounds. Across the street, deeded beach access leads to the powdery white sands and turquoise waters of the Gulf of Mexico, where unforgettable sunsets become part of everyday life. The pet-friendly community also offers on-site laundry facilities and optional rental management services, including housekeeping, beach loungers, umbrellas, and guest services, making ownership effortless. Perfectly positioned just moments from Historic Bridge Street, you'll enjoy easy access to waterfront restaurants, local boutiques, live entertainment, fishing charters, and island cafés. The free Anna Maria Island Trolley stops nearby, providing convenient transportation to Holmes Beach, Anna Maria, Coquina Beach, and additional island attractions. Whether you're spending your days boating, paddleboarding, shelling along the shoreline, or exploring the island's vibrant dining scene, this exceptional residence offers the quintessential Anna Maria Island lifestyle with outstanding rental potential.

1603 Gulf Drive N Unit 3, Bradenton Beach
$675,000
1 Beds ⋅ 1 Baths ⋅ 5400 Condos SubDv. ⋅ 34217 Zip Code
1+ BEDROOM BEACHFRONT CONDO WITH NO FLOOD DAMAGE, offered fully furnished and move-in ready in one of Anna Maria Island's most welcoming communities. Rarely does an affordable beachfront opportunity like this become available. Enjoy the perfect blend of island comfort, convenience, and community, with condo fees covering nearly everything except electricity, making ownership simple and stress-free. Start your mornings with sunrise walks along the Gulf, spend afternoons poolside, and end your evenings watching spectacular sunsets from the beachfront community patio while visiting with neighbors and friends. Inside, you'll find a spacious living area with neutral coastal décor, creating a relaxed atmosphere for gathering with family and friends after a day at the beach. The versatile bonus room provides the flexibility to create an additional sleeping area, comfortably accommodating up to four adults. Enjoy peaceful courtyard views overlooking the lush tropical landscaping from your private patio, the perfect spot for morning coffee or evening relaxation. The kitchen features wood cabinetry and granite countertops, and the dining area includes an expandable table for entertaining guests. Ample storage is available with four interior closets plus a large exterior storage closet for all your beach gear. Additional features include 8-foot ceilings, in-unit laundry, covered parking, and guest parking. Here, the beach isn't just nearby—it's part of everyday life. Step outside and within moments your toes are in the sand. Spend your days enjoying two large heated community pools, beautifully maintained grounds, and tropical landscaping that creates a true resort-style setting. The community clubhouse hosts social gatherings and offers additional laundry facilities for owners. Properties in this highly sought-after beachfront community rarely become available. More than just a condo, this is an opportunity to embrace the relaxed island lifestyle and own a special piece of paradise that is becoming increasingly difficult to find. *Only Murphy bed photos are virtually staged showing the versatile use for the bonus room/sun room as a second sleeping area for guests.

5400 Gulf Drive Unit 18, Holmes Beach
$559,000
2 Beds ⋅ 2 Baths ⋅ Westbay Cove SubDv. ⋅ 34217 Zip Code
From the elevated and coveted 2nd (Top) floor, Experience the ultimate Anna Maria Island lifestyle in this beautifully updated and turnkey-furnished condo at Westbay Cove in the heart of Holmes Beach. Perfectly positioned just steps from the sugar-sand beaches and turquoise Gulf waters, this spacious residence offers the ideal blend of relaxed coastal living, investment potential, and resort-style amenities. Inside, the bright and inviting open floor plan is filled with natural light and designed for effortless island living. The condo features a spacious primary bedroom, a second spacious bedroom with two queen beds for guests, a beautifully updated kitchen, comfortable living area, and a private sunroom overlooking lush tropical landscaping and the pool area — creating the perfect setting for morning coffee or sunset cocktails. Offered fully furnished and move-in ready, this property is ideal as a primary residence, vacation getaway, or income-producing investment.

600 Manatee Avenue Unit 227, Bradenton Beach
$695,000
2 Beds ⋅ 2 Baths ⋅ Runaway Bay SubDv. ⋅ 34217 Zip Code
Welcome to Runaway Bay an island-style waterfront community in Bradenton Beach offering the ideal combination of coastal living and income potential, with weekly rentals permitted. This beautifully updated 2-bedroom, 2-bath ground-level condo showcases breathtaking open water views across Anna Maria Sound and Palma Sola Bay. Step inside to discover a stunning, fully remodeled coastal kitchen that has been thoughtfully opened to the living and dining areas creating a bright, airy space perfect for entertaining while maximizing the spectacular bay views. Natural light pours in, drawing your attention straight to the water. The spacious primary suite offers a peaceful retreat, where you can wake each morning to unforgettable sunrises over the bay. A generous walk-in closet and a beautifully renovated ensuite bath add to the comfort and functionality. The guest bedroom is equally inviting and conveniently located next to the updated guest bathroom. Start your day with coffee on the private lanai as the sun rises, and spend your evenings watching dolphins play and enjoying the tranquil coastal surroundings. This condo has been extensively updated, including the kitchen, bathrooms, flooring, trim, doors, appliances, water heater, A/C system, and furnishings making it truly move-in or rental ready. Runaway Bay has also undergone community-wide improvements, including new roofs and gutters, and offers an impressive lineup of resort-style amenities: deeded beach access, a newly constructed oversized bayfront observation and fishing pier, the largest heated pool on Anna Maria Island (recently renovated), resurfaced pickleball and tennis courts, shuffleboard, a kayak launch, multiple grilling stations, and a clubhouse with a fitness center currently being refreshed. Whether you’re seeking a personal island escape or a high-performing investment property, this condo delivers with strong rental history and bookings already secured.

1801 Gulf Drive N Unit 142, Bradenton Beach
$769,000
2 Beds ⋅ 3 Baths ⋅ Anna Maria Island Club SubDv. ⋅ 34217 Zip Code
Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.

101 66th Street Unit 6, Holmes Beach
$600,000
2 Beds ⋅ 2 Baths ⋅ Westbay Point SubDv. ⋅ 34217 Zip Code
ANNA MARIA ISLAND, FULLY FURNISHED 2 bed 2 bath, perfectly situated 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 neighborhood 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. Enjoy a cozy atmosphere with local bike shop, restaurants, shopping options, and multiple access points to the beach.

6400 Flotilla Drive Unit 15, Holmes Beach
$700,000
2 Beds ⋅ 2 Baths ⋅ Waterline Villas & Marina SubDv. ⋅ 34217 Zip Code
Experience the ultimate in resort-style living at Waterline Villas & Marina, nestled on the picturesque Holmes Beach of Anna Maria Island. This beautifully appointed corner unit with a highly sought after floor plan features a 2-bedroom, 2-bathroom condo that offers a seamless blend of coastal charm and modern sophistication. Enter through French doors into a welcoming hallway that leads you to the spacious guest bedroom, featuring two queen-sized beds and an ensuite bathroom. The inviting atmosphere is perfect for family or friends, with ample room and comfort. As you continue through the unit, you'll be drawn to the heart of the home; the open-concept kitchen and living area. Warm wood accents throughout create a cozy, coastal ambiance. The living room offers a comfortable space to relax and unwind, with access to the expansive balcony overlooking the serene pool and canal. The primary suite is a true retreat, complete with a king-sized bed and an ensuite bathroom for added privacy and convenience. Each area of the condo opens to the balcony, enhancing the indoor-outdoor living experience. This prime location within the building offers views of the canal and intercoastal waters, setting the stage for memorable moments. Waterline Villas & Marina is not just a place to stay; it’s a destination. Enjoy resort-like amenities such as an on-site restaurant, fitness center, and a banquet room. For the water enthusiast, boat slips are available on a first-come, first-served basis, and bicycle rentals make exploring the island a breeze. Part of Marriott's Autograph Collection, this unit benefits from professional management, ensuring a consistent revenue stream year after year. The unit is zoned to allow owners to occupy it for up to 120 days annually, providing a flexible ownership experience with the option to enjoy the property personally or generate income through nightly rentals. With a strong rental history, prime location, and luxury amenities, this condo offers a unique opportunity for both personal enjoyment and investment. Don’t miss the chance to own a piece of paradise at Waterline Villas & Marina.

5325 Marina Drive Unit 128, Bradenton Beach