Anna Maria Homes with Private Pool type

Anna Maria Homes with Private Pool type

Welcome to Anna Maria, Florida – a hidden gem nestled in Manatee County, where coastal charm meets vibrant island life. Known for its stunning white sandy beaches and crystal-clear waters, Anna Maria is the perfect destination for those seeking a slice of paradise. This quaint island town boasts a laid-back atmosphere, making it an ideal retreat for families, retirees, and anyone looking to escape the hustle and bustle of everyday life.

One of the most sought-after features of homes in Anna Maria is the presence of private pools. Imagine stepping out of your beautifully designed home and diving into your own tranquil oasis, surrounded by lush tropical landscaping. Homes with private pools in Anna Maria offer the perfect blend of relaxation and luxury, allowing you to soak up the sun in complete privacy or host delightful gatherings with friends and family. Whether you’re sipping cocktails poolside or enjoying a sunset swim, having your own pool elevates the island living experience.

In addition to the allure of private pools, Anna Maria is renowned for its unique boutiques, delicious dining options, and a plethora of outdoor activities. From kayaking through mangroves to fishing off the piers, the opportunities for adventure are endless. With a strong sense of community and a welcoming spirit, Anna Maria is not just a place to live; it’s a lifestyle.

Discover your dream home with a private pool in Anna Maria, where every day feels like a vacation. Embrace the island life and make memories that will last a lifetime in this enchanting Florida paradise.

Newest Anna Maria Homes with Private Pool type

783 Jacaranda Road, Anna Maria
$1,999,000
3 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Paradise awaits on the coveted North End of Anna Maria Island! This 3 bedroom/2 bath pool home welcomes you with cathedral ceilings and family room open to the updated kitchen and dining room. Extend your relaxation to the screened porch with new Trex decking, overlooking your private, fenced backyard pool and covered dining area. Your guests will relax in their first floor bedrooms, while you will enjoy your upstairs primary en suite with peeks of the gulf, and an attached open loft. You’ll also love the second floor screened porch with great Gulf breezes! Downstairs there’s ample storage for beach toys and you’re only a hop, skip & a jump to your toes in the sand. With short term rentals allowed, this great space is an ideal investment property in the city of Anna Maria!

783 Jacaranda Road, Anna Maria
607 S Bay Boulevard, Anna Maria
$2,150,000
4 Beds ⋅ 3 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code
This 4 bedroom, 3 bathroom waterfront home on a canal with spectacular outdoor space with multiple decks and both bay and canal views! The home is situated at the north end of the island within an easy bike or golf cart ride to Anna Maria's Pine Avenue shops, the bayside beach, Anna Maria City Pier and gulf-side beaches! The pool is heated and the spa provides some extra warmth and relaxation at the end of a fun beach day! The home has a great backyard area with an outdoor shower and there is small private dock perfect for wetting a line or launching your kayak! The main floor is a gorgeous open concept living, dining, kitchen area. The huge kitchen island and breakfast bar has counter seating with stainless steel high-end appliances. You will be able to whip some fabulous meals at home or prep some libations for entertaining on one of the home's spacious covered balconies! There are two balconies on the first floor alone off both the front and back of the home with plenty of seating! The main floor has the master suite with closet, TV and en-suite full bathroom with tub/shower combination accessible from the living room as well. The top floor has 3 additional bedrooms. There are two additional covered decks off the front and back with bay and canal views respectively. The best of both worlds, this home has so much to offer!

607 S Bay Boulevard, Anna Maria
313 Magnolia Avenue, Anna Maria
$1,595,000
3 Beds ⋅ 2 Baths ⋅ Bimini Bay Colony Club Sub SubDv. ⋅ 34216 Zip Code
Welcome to Mangoes on Magnolia, a three-bedroom, two-bath vacation home with a private heated pool and hot tub, located less than a 10-minute walk from the white-sand beaches of Anna Maria Island. Nestled in a quiet neighborhood just two blocks from Pine Avenue’s shops and restaurants. This coastal retreat is perfect for families and friends. After sunny days on the beach, return to your lagoon-style heated pool and hot tub, the ultimate relaxation spot. Gather around the outdoor wood dining table by the pool to share meals in the fresh island air. With a bonus game room, Mangoes on Magnolia offers plenty of ways to keep everyone entertained. Step inside to a bright coastal living area ideal for relaxing after a day of island adventures. The fully equipped kitchen makes cooking simple, with two refrigerators, island seating, and all the essentials for preparing meals. Gather around the dining table for family dinners before heading to the bonus room for games and reading. The primary bedroom is a peaceful retreat, ample storage, and an ensuite bathroom with a step-in shower. The second bedroom also features a queen bed, while the third bedroom offers a full bed, making it perfect for kids or additional guests. The hallway bathroom includes a tub/shower combo and a spacious vanity. Guests love this home’s unbeatable location. Stroll to the boutiques and eateries on Pine Avenue, hop on the island trolley, or explore the natural beauty of Anna Maria Island by bike, kayak, or on foot. With spectacular sunsets just a short walk away, Mangoes on Magnolia makes it easy to enjoy the very best of island living.

313 Magnolia Avenue, Anna Maria
254 Gladiolus Street, Anna Maria
$1,845,000
3 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Located at the North End of Anna Maria Island 3 blocks from the beach and 1 block from the bay. Three bedrooms, 2 bathrooms with open living & dining floor plan that leads to a large screened porch for grilling, dinning and ping pong! Perfect for entertaining your friends and family. Freshly painted interior, natural light throughout, stainless steel appliances in the kitchen with a huge island. Downstairs has privacy landscaping, turf surrounding the heated pool and spa. Featuring an oversized 4-car garage with additional parking space available for a boat out front. Currently a vacation rental with a 1-7 day minimum. Schedule your private showing today.

254 Gladiolus Street, Anna Maria
515 Loquat Drive, Anna Maria
$4,995,000
4 Beds ⋅ 5 Baths ⋅ Lacios Sub SubDv. ⋅ 34216 Zip Code
Welcome to 515 Loquat Drive. This exceptional waterfront residence on Anna Maria Island offers a refined blend of coastal elegance, thoughtful design, and effortless island living. Set along a peaceful canal, this impressive 4-bedroom, 4.5-bathroom home features a private dock, elevator, rooftop deck, and beautiful bay views, with Pine Avenue, local dining, and the free island trolley just a short walk away. Currently operating as a successful vacation rental, this property offers an excellent opportunity for both personal enjoyment and investment. Inside, the bright, open layout is designed for both everyday comfort and entertaining. The spacious living area flows seamlessly into a gourmet kitchen with high-end appliances and a generous island, while a wet bar and dedicated office add convenience and versatility. Each of the four well-appointed bedrooms features its own ensuite bathroom, with three offering king beds and the fourth including two twin-over-full bunk beds. The primary suite provides a private retreat with a soaking tub and walk-in shower. Outdoor living is equally impressive, with a private heated pool, oversized spa, and multiple lounging and dining areas. Enjoy morning coffee by the water, gather around the pool, or take in spectacular sunsets from the rooftop deck. The private dock offers convenient waterfront access, while the home's elevated design and island location create an exceptional setting for enjoying the best of Anna Maria Island. With its desirable waterfront setting, generous living spaces, impressive indoor-outdoor amenities, and successful vacation rental history, 515 Loquat Drive presents a rare opportunity to own a beautifully appointed island home in one of Florida's most sought-after coastal destinations.

515 Loquat Drive, Anna Maria
242 Lakeview Drive, Anna Maria
$6,995,000
6 Beds ⋅ 7 Baths ⋅ Lake La Vista Sub SubDv. ⋅ 34216 Zip Code
Introducing The Ivy — The first chapter in a new collaboration. Born from the partnership of Emily Moss Designs and Moss Builders, The Ivy marks the debut of their shared vision on Anna Maria Island — a carefully crafted waterfront residence where refined design and thoughtful construction meet. As the inaugural home in what will become a growing collection, The Ivy sets the tone for the work to come: elevated, intentional, and deeply rooted in the island’s quiet luxury. Step through the front entry — sheltered beneath a soaring tongue-and-groove wood ceiling — into a great room where large-format stone flooring, disappearing glass sliders, and a sculptural wood ceiling detail set a calm, organic tone. The chef's kitchen anchors the main level with a monumental waterfall-edge stone island, custom dark wood cabinetry, and sculptural globe pendant lighting, flowing seamlessly into a dining room defined by a dramatic wood-beamed vaulted ceiling, a statement orb chandelier, and floor-to-ceiling glass that frames water views from every seat at the table. Directly off the kitchen you’ll find a huge walk in pantry. Six bedrooms offer their own quiet retreats — from a serene primary suite with an upholstered headboard and private glass sliders, to a playful bunk room with built-in cubby storage for kids. The six and a half bathrooms are spa-like in their own right, with freestanding vessel sinks, brass fixtures, and dramatic veined stone and designer tile work throughout. Outside, The Ivy truly comes alive. A resort-style pool is anchored by an elevated spa with a cascading water feature, framed by a turfed lawn, lounge chairs, and a covered wood-ceilinged loggia built for shaded entertaining. A dramatic timber trellis staircase first leads up to the outdoor kitchen, massive TV and hanging swings. As you continue to make your way up to the crown jewel: a expansive rooftop deck with built-in bench seating, a private hot tub to enjoy sunsets, lounge chairs and seating around a fire pit. Direct canal front access completes the picture, with a brand-new dock and boat lift ready for a day on the water — all just a short, palm-lined walk to the shops and restaurants of Pine Avenue.

242 Lakeview Drive, Anna Maria
259 Gladiolus Street, Anna Maria
$2,690,000
4 Beds ⋅ 3 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code
Under Construction. Welcome to this completely updated charming coastal home located at 259 Gladiolus St in the desirable City of Anna Maria. If you’re looking for a ground level waterfront, 4-bedrooms, 3-bathrooms, pool home on the north-end, that is close to the beach, Pine Ave shops and the bayside park, this is one to come see! The interior and exterior design offers endless charming coastal details that lean into island relaxed style. As you walk through the double glass front doors, you’ll be surprised by how much light shines into this home accentuating the high ceilings and open concept. The design selections are classic and calm, from neutrals to soft beachy blues. The home offers a split floor plan and two master ensuites plus an inside utility that takes the chore out of laundry. As you make your way to the back of the home the water views become the focal point. The home layout makes every day enjoyment of island living, including the pool and spa that has multiple water features to create relaxing sounds and set the stage for backyard fun. The waterfront setting is tranquil and a fabulous setting for dockside fishing, kayaks or even boating with two bridges to bay. The list of new items includes interior walls and open concept layout, electric, plumbing, flooring, kitchen, appliances, bathrooms, inside utility, metal roof, Therma Tru impact glass front door and PGT impact windows and sliding doors, heated pool/spa, tropical landscaping, and including low maintenance artificial turf. Whether you’re looking for your own island destination to call home or the ideal rental income property with flexible rental restrictions this is one to consider. Call today to schedule your private showing.

259 Gladiolus Street, Anna Maria
508 Spring Avenue, Anna Maria
$3,300,000
5 Beds ⋅ 4 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
Welcome to Spring House! Invest in one of Anna Maria Island’s most desirable locations with this exceptional 5-bedroom, 4-bath turnkey rental, just steps from Pine Avenue’s charming shops, restaurants, and the iconic Anna Maria Pier—and only a short bike ride to Bean Point. A true rental powerhouse, this property has generated well over $200,000 in gross rental income while still allowing time for owner use. One of the few properties on Anna Maria Island with Bert Harris approval for occupancy of up to 14 guests, this home offers a rare combination of income potential and flexibility. The beautifully landscaped backyard is designed for maximum guest appeal, with a heated lagoon-style pool, shallow splash area, built-in dining/bar area, Adirondack seating, and BBQ grill. A dedicated recreation room adds even more entertainment value with a flat-panel TV, foosball, ping pong, and a large sitting area. The spacious primary suite includes a king bed, private balcony access, and an ensuite bathroom with a double vanity and newly renovated walk-in shower. Four additional bedrooms and two living room areas provide flexible sleeping arrangements for large groups. Room Details: * Primary Suite – 2nd Floor: King bed, balcony access, ensuite bath. * Second Bedroom – 2nd Floor: King bed. * Third Bedroom – 2nd Floor: Twin bunk bed + twin bed + twin trundle bed. * Fourth Bedroom – 1st Floor: King bed, ensuite bath. * Fifth Bedroom – 1st Floor: Twin bunk bed + twin bed + twin trundle bed. Turnkey and rental-furnished with Wi-Fi, XBOX gaming system, and assorted beach equipment. Strong rental history, exceptional guest capacity, premier location, and an impressive resort-style outdoor space make this a standout investment opportunity on Anna Maria Island. PROVEN RENTAL INCOME • BERT HARRIS APPROVED • PRIME ANNA MARIA ISLAND LOCATION

508 Spring Avenue, Anna Maria
113 Palmetto Avenue, Anna Maria
$5,125,000
4 Beds ⋅ 5 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
A rare opportunity awaits just steps from the Gulf in this exceptional 2025 coastal residence by Eason Builders Group. Set west of Gulf Drive in one of Anna Maria Island’s most desirable locations, this four-bedroom, four-and-a-half-bath home blends refined interiors, resort-style outdoor living and the relaxed sophistication of island life. From the moment you arrive, the home makes a striking impression with crisp coastal architecture, multiple balconies, lush tropical landscaping and contemporary black-framed windows. Inside, soaring ceilings, warm wood flooring, abundant natural light and thoughtfully selected designer finishes create a refined yet relaxed atmosphere. The open-concept main living level is designed for both entertaining and everyday enjoyment. At the heart of the home, the chef’s kitchen features an oversized island with generous seating, custom cabinetry, stone countertops, premium finishes and abundant storage. The kitchen flows seamlessly into the dining area and dramatic great room, where expansive walls of glass, a sleek contemporary fireplace and oversized sliding doors connect beautifully to the outdoor spaces. A private residential elevator provides convenient access between levels, adding comfort and functionality for owners and guests alike. Each of the four bedrooms offers a beautifully appointed retreat, complemented by spa-inspired baths with sophisticated tilework, glass-enclosed showers and designer finishes. The primary suite features a luxurious bath with dual vanities, an oversized walk-in shower and freestanding soaking tub. Custom closet systems, elevated millwork and carefully considered details are found throughout. Outdoor living is at the center of the experience. The private backyard is a tropical resort with a stunning pool and elevated spa, lush landscaping and generous covered areas for lounging, dining and entertaining. Crowning the residence is an expansive rooftop deck offering panoramic island and Gulf views and an unforgettable setting for morning coffee, sunset gatherings or evenings under the stars. Multiple balconies provide even more opportunities to enjoy the Gulf breezes. Currently operating as a highly successful vacation rental, the property offers exceptional versatility as an income-producing investment, luxurious second home or full-time residence. With projected annual rental revenue of approximately $400,000, the home presents a compelling investment opportunity while delivering the lifestyle expected of a premier Anna Maria Island property. Leave the car behind and embrace island life—walk to the beach in moments, cruise the island by golf cart or bicycle, spend afternoons boating and fishing, and enjoy the boutiques, galleries, waterfront dining and acclaimed restaurants that make Anna Maria so special. Combining 2025 construction, exceptional craftsmanship, sophisticated coastal design, a private elevator, resort-style pool and spa, rooftop entertaining space, strong rental potential and an extraordinary west-of-Gulf-Drive location, this remarkable residence offers a rare opportunity to own a true luxury retreat on Anna Maria Island.

113 Palmetto Avenue, Anna Maria
315 Hammock Circle, Anna Maria
$2,595,000
3 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34216 Zip Code
Welcome to your private coastal retreat in the highly sought-after North End of Anna Maria Island. Completely remodeled from the studs out in 2017 by Gagne Construction, this elevated 3-bedroom, 3.5-bathroom home is situated on a spacious 0.21-acre lot, just a short stroll from the island’s famous white sand beaches and only a couple of minutes on foot from Pine Avenue, the heart of Anna Maria’s shops, restaurants, and island attractions. This superb location allows you and your guests to easily experience the best of the island without ever needing to get in the car. Offering the ideal combination of luxury, comfort, and laid-back island living, this fully furnished residence is perfect as a personal getaway, second home, or investment property with excellent rental potential. Inside, the thoughtfully designed open floor plan is filled with natural light and complemented by high-end finishes throughout. Hurricane impact windows and sliding glass doors provide added protection and peace of mind, while enhancing the home’s seamless connection to its tropical surroundings. The spacious living areas flow effortlessly into the modern kitchen, which features top-of-the-line appliances and plenty of room for gathering with family and friends. Each oversized bedroom offers its own private en-suite bathroom, while elegant, spa-inspired finishes contribute to the home’s relaxed yet refined coastal atmosphere. The outdoor living space is equally impressive and has recently been refreshed with new landscaping, new exterior paint, and new outdoor furniture. Lush tropical surroundings, a heated pool, and an oversized lanai create your own private island oasis. Spend the afternoon by the pool, enjoy dinner al fresco, or unwind outdoors after a day at the beach. The seamless indoor and outdoor layout is perfectly suited for entertaining, extended stays, and creating the type of vacation experience guests will want to enjoy again and again. Offered fully furnished and move-in ready, this home makes second-home ownership effortless while also providing the flexibility to generate rental income when you are away. Anna Maria Island is celebrated for its pristine beaches, tranquil waters, fresh local seafood, and charming small-town atmosphere. With Pine Avenue just moments away, this exceptional North End location places the very best of island living right outside your door. This is a rare opportunity to own a beautifully appointed island retreat where you can vacation, relax, entertain, and invest.

315 Hammock Circle, Anna Maria
159 Crescent Drive, Anna Maria
$2,849,000
4 Beds ⋅ 3 Baths ⋅ Lake La Vista Sub SubDv. ⋅ 34216 Zip Code
***Huge market price adjustment before before season is upon us.*** Welcome to Tropical Paradise. Talk about Location, Location, Location. What more can you ask for in the City of Anna Maria? Three houses and 200 steps to the calm beaches at Bayfront Park. It’s an easy walk to the City Pier, the Waterfront Restaurant and all the shops of Pine Ave. It is the perfect home for any of your needs. Make it your full-time residence. Use it as a second home, turn it into a fabulous vacation rental or combine the two. This home was built in 2007. It is elevated, has hurricane strength windows and doors, and has superior hurricane protection with a metal roof. All these factors lower your insurance costs dramatically. The home has 2567 SF of air-conditioned space on two floors. It has received major updates with 2 new HVAC units and a new hot water heater. When you pull up in front of the home you are greeted by two large decks overlooking the street and from the top floor views of Tampa Bay. These decks have both been re-surfaced and weather-proofed with new wood look ceramic tiles. The stairs and deck leading to the front door were rebuilt with Trex decking. There is a large double wide car garage door opening into a massive 4 car garage that goes from the front to the back of the home. There is a direct access staircase to the living space from the garage. Go up the front stairs onto the first floor of the home. All the flooring throughout the home are re-done with weatherproof luxury vinyl planking. There is a large open-air floor plan with a comfortable great room, huge dining area and updated kitchen with granite counters, a tile back splash, breakfast bars, and stainless-steel appliances. Also on this level is one of the four bedrooms. It has an in-suite bath with a re-tiled walk-in shower and a new vanity. The kitchen and bedroom both have access to a rear porch with a spiral staircase leading down to the backyard and pool. Going up to the third floor you have three bedrooms starting with a spacious primary suite. It has two walk-in closets and a private bath suite with a walk-in shower, jacuzzi soaking tub and a new large dual vanity. There are French doors from the master bedroom opening onto the front balcony. From here, there are views of Tampa Bay and the Skyway Bridge. The two other bedrooms share a hallway bath with a new vanity, Both bedrooms have French doors with access to a rear enclosed and air-conditioned playroom. The hallway bath has a private bathtub and a new vanity. Last, there is a large laundry room with a full sized washer and dryer. On each level you will find a large storage closet. These closets are preparation for an elevator shaft, should you want or need one. The garage is big enough for all your toys. At the back of the garage are patio doors leading out to your private Astroturf back yard and heated pool. You can easily turn the back of the garage into gathering area overlooking the pool. The yard has an eight-foot rear fence for added privacy. From your front door, it is less than a 2-minute walk to the calm beaches of Bayfront Park in Tampa Bay Here there are changing rooms, showers, gazebos, and charcoal grills for a picnic on the bay. If you prefer the Gulf, it is about a 10-minute walk from the house. The free AMI trolley-stop, and Pine Ave with all its restaurants and shops are just down the street. This home is offered turn-key furnished and presently being booked in an active rental program.

159 Crescent Drive, Anna Maria
76 N Shore Drive, Anna Maria
$1,750,000
4 Beds ⋅ 4 Baths ⋅ Bimini Bay Colony Club Sub SubDv. ⋅ 34216 Zip Code
An income-producing opportunity in the heart of Anna Maria Island. This 4-bedroom, 4-bathroom duplex sits on coveted North Shore — steps from the boutiques, cafés, and galleries of Pine Avenue and minutes from the Gulf's world-famous sugar-white beaches. Blue Lagoon operates as a vacation rental with a proven track record, a loyal returning guest base, and confirmed reservations already booked into 2027. The property features a large heated pool, private outdoor entertaining areas in-unit washers/dryers, and an on-site EV charger. The duplex can be rented as two separate units or opened via an interior connecting door to accommodate larger groups, maximizing both flexibility and revenue potential year-round. Bert Harris Agreement — A Significant Asset This property benefits from a Bert Harris Private Property Rights Agreement with the City of Anna Maria. When the city enacted its vacation rental ordinance limiting all short-term rentals to a maximum occupancy of 8 guests regardless of home size, many property owners successfully filed claims under Florida's Bert J. Harris Jr. Private Property Rights Protection Act, a state law that protects owners when a local government action reduces the value of their property. Through a negotiated settlement, this property secured the right to host up to 12 guests, well above the city's standard cap. This agreement transfers with the property and represents a meaningful competitive and financial advantage that cannot easily be replicated by new purchasers today. A true turnkey investment in one of Florida's most sought-after island destinations.

76 N Shore Drive, Anna Maria
Start Your Search

How much is your home worth?

Get instant property value now!