Anna Maria Vacation Homes for Sale

Welcome to Vacation.RealEstate, your gateway to premium vacation and investment properties in Anna Maria, FL — one of Florida’s most charming and sought-after coastal destinations. Whether you’re dreaming of a beachfront escape, a family-friendly retreat, or a high-yield short-term rental, Anna Maria offers a rare mix of island serenity and smart real estate potential.

Why Choose Anna Maria?

Tucked away on the northern end of Anna Maria Island, this vibrant beach town is beloved for its Old Florida charm, sugar-sand beaches, and laid-back island lifestyle. Here’s why investors and vacation homebuyers are flocking here:

  • Strong Vacation Rental Market – High occupancy rates & excellent ROI

  • Limited Inventory – Zoning laws help preserve value and exclusivity

  • Walkable Beach Town – No high-rises, just sun, surf, and local flavor

  • Natural Beauty – Gulf views, native wildlife, and postcard sunsets daily

Anna Maria Island Vacation homes for sale
Anna Maria Beachfront Homes for Sale
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What You'll Find in the Listings Below

Scroll down to explore the latest active property listings in Anna Maria, our listings include:

  • Gulf-Front & Beach Access Homes

  • Luxury Villas & Modern Coastal Estates

  • Waterfront Properties with Private Docks

  • Classic Cottages & Renovated Bungalows

  • Turnkey Vacation Rentals with Proven Income

Each listing includes detailed descriptions, high-res photos, and real-time availability to help you find your perfect island escape or investment.

Not Sure Where to Start?

If you’re new to the Anna Maria real estate market, we’re here to help. From identifying the best neighborhoods and rental zones to navigating city ordinances and short-term rental licenses, our local team provides expert guidance every step of the way.

📞 Contact us today for personalized advice or to schedule a showing.

👉 Get in Touch

Explore Anna Maria Properties Below

Real-time listings are updated daily. Start your search now and find your dream home in paradise.

👇 Browse the latest homes for sale in Anna Maria, FL below.

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511 Spring Ave, Anna Maria, Florida 34216

Residential For Sale

BLUESRQ REAL ESTATE INC
Welcome to Cabana Breeze, an elevated, eco-friendly retreat on the coveted north end of Anna Maria Island. Complete with solar panels—this four-bedroom, two-bath home sits just a short walk from Anna Maria City Beach and steps from Pine Avenue’s popular shops and restaurants.
$1,825,000
4Bedroom(s)
2Bathroom(s)
1,248Sqft
More Details

771 Jacaranda Rd, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
Welcome to Limelight — a beautifully appointed and fully furnished 3-bedroom, 2-bath coastal retreat ideally located on the coveted north end of Anna Maria Island, just steps from direct beach access. Light-filled interiors and swaying palms greet you upon entry, setting the tone for relaxed island living.
$1,799,000
3Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
1,447Sqft
More Details

311 Poinsettia Rd, Anna Maria, Florida 34216

Residential For Sale

WEICHERT REALTORS EXCLUSIVE PROPERTIES
Experience the ultimate coastal retreat at 311 Poinsettia Rd in Anna Maria, FL—a home where luxury meets laid-back island living. This beautifully renovated, elevated sanctuary boasts stunning waterfront views, a sparkling pool, and your very own private boat dock with a lift, inviting endless adventures on the water.
$1,775,000
3Bedroom(s)
2Bathroom(s)
DrivewayParking(s)
1,296Sqft
More Details

401 N Bay Blvd, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
One or more photo(s) has been virtually staged. Perfectly positioned just steps from the sparkling turquoise waters of Tampa Bay and the white sandy beaches, this elevated island home offers breathtaking views of the iconic Skyway Bridge and a front-row seat to the beauty of Anna Maria's coastal charm.
$1,775,000
2Bedroom(s)
3Bathroom(s)
Workshop in GarageParking(s)
1,710Sqft
More Details

717 Jacaranda Rd, Anna Maria, Florida 34216

Residential For Sale

KW COASTAL LIVING II
Located just one block from the beach this is a rare land-value/structure value opportunity on .29 Acres in one of Anna Maria Island’s most coveted coastal neighborhoods. Ideally located just a block off the pristine Anna Maria beach and Bean Point.
$1,750,000
5Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,543Sqft
More Details

313 Magnolia Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestled in a prime location midway between the enchanting Tampa Bay and the pristine Gulf of Mexico waters, this meticulously maintained home offers the perfect blend of convenience and relaxation.
$1,675,000
3Bedroom(s)
2Bathroom(s)
1,424Sqft
More Details

412 Alamanda Rd, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, floating in a pool or lounging at your very own tiki bar. Light and bright open concept floor plan and impact sliders that open up to the pool and backyard oasis. This home is offered turnkey furnished and ready to move in or ready to be a great vacation rental. Zoned for 1-7 days.
$1,650,000
2Bedroom(s)
2Bathroom(s)
1,168Sqft
More Details

521 South Drive, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Enjoy living in a beautiful canal front home on Anna Maria Island offers a multitude of benefits for those who appreciate waterfront living and outdoor activities. With convenient access to both the Gulf of Mexico and Tampa Bay, the Galati Marina you'll have endless opportunities to explore the waterways and enjoy various recreational activities.
$1,650,000
2Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,470Sqft
More Details

709 Gladiolus St, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Great opportunity for investors and homeowners to start over and design to your very own taste! Flood damage from Hurricane Helene- Ideal for Renovation or Rebuild, Whether you're looking to remodel the existing structure or embark on a new construction project, this property offers a solid foundation and ample space to bring your vision to life. Plans drawn up and available upon request.
$1,595,000
4Bedroom(s)
3Bathroom(s)
1,933Sqft
More Details

309 Pine Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
RARE MIXED-USE OPPORTUNITY ON PINE AVE! Welcome to 309. Pine Avenue—one of the few properties on Anna?Maria Island with coveted ROR zoning (Retail/Office/Residential), giving you the freedom to live, lease, or launch a business all on one site. Front Cottage Coastal-chic 2-bedroom residence, freshly remodeled.
$1,585,000
2Bedroom(s)
1Bathroom(s)
DrivewayParking(s)
936Sqft
More Details

239 Gladiolus St, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
Under contract-accepting backup offers. Welcome to your island retreat on beautiful Anna Maria Island. Tucked away on the quiet north end, this elevated three-bedroom, two-bath home was originally crafted by Whitehead Construction, known for their quality coastal builds.
$1,450,000
3Bedroom(s)
2Bathroom(s)
1,296Sqft
More Details

120 Hammock Rd, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
120 HAMMOCK ROAD IS A DREAM LOCATION. SITUATED ON THE NORTH END OF ANNA MARIA ISLAND AND NESTLED ON A QUIET DEAD END STREET. SURROUNDED BY NATURAL BEAUTY. IT IS THE PERFECT PLACE TO LIVE THE ISLAND LIFESTYLE. IT SITS JUST A SHORT WALK OR BIKE RIDE TO THE RESTAURANTS AND SHOPS ON PINE AVE.
$1,425,000
3Bedroom(s)
3Bathroom(s)
1,912Sqft
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