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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111 Cedar Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVAILABLE WEST OF GULF DRIVE! THIS HOME ALSO COMES WITH A BOAT SLIP AND 10,000 LB BOAT LIFT!!! IT DOES NOT GET BETTER THAN THIS! STEPS TO BEACH AND THE WATERFRONT LIFESTYLE! This exquisite retreat offers the perfect blend of luxury, comfort, and convenience.
$3,895,000
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,263Sqft
More Details

113 Maple Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
THIS INCREDIBLE CUSTOM BUILT ESTATE IS JUST FIVE HOUSES FROM THE GULF AND NESTLED ON ONE OF THE MOST COVETED STREETS ON ANNA MARIA ISLAND!!! LOCATED WEST OF GULF DRIVE YOU ARE JUST STEPS FROM THE SUGAR-WHITE SANDS AND TURQUOISE WATERS! This beautifully designed coastal home offers over 2,600 square feet of light-filled living space and is currently operating as a successful vacation rental, making
$3,690,000
5Bedroom(s)
5Bathroom(s)
2,680Sqft
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108 Tern Dr, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
Under contract-accepting backup offers. Welcome to your island oasis! This stunning modern waterfront home redefines relaxation. Step through the double front doors and behold the tropical backyard. Ascend to the main living level via custom handrail-adorned stairs or the convenient elevator.
$3,550,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
3,874Sqft
More Details

421 Alamanda Rd, Anna Maria, Florida 34216

Residential For Sale

MICHAEL SAUNDERS & COMPANY
Welcome to Luxe Island Escape, an exceptional 4-bedroom, 4.5-bath coastal retreat nestled in the tranquil heart of Anna Maria Island. This captivating residence is offered fully turnkey furnished—ready for you and your family to immediately embrace the island lifestyle.
$3,499,000
4Bedroom(s)
5Bathroom(s)
2,116Sqft
More Details

120 White Ave, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
Nestled on Anna Maria Island’s most famous street, this beautifully renovated coastal retreat boasts five spacious bedrooms and four luxurious bathrooms, offering the perfect blend of comfort and style. Designed for seamless indoor-outdoor living, it features multiple porches where you can bask in the island breeze.
$3,497,500
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,763Sqft
More Details

408 Magnolia Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Welcome to Boundless Waves, a new, custom-built coastal estate that perfectly captures the essence of luxury island living on beautiful Anna Maria Island. This exceptional six-bedroom, six-and-a-half-bath residence spans over 3,500 square feet and was thoughtfully designed with no expense spared and no detail overlooked.
$3,490,000
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
3,545Sqft
More Details

705 N Shore Dr, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA LIFE REAL ESTATE
Stunning Family Vacation Home in Anna Maria, FL! Yellowbird, 705 North Shore Dr., Anna Maria. Nestled on the beautiful North End of Anna Maria Island, Yellowbird is a luxurious family vacation home that embodies old Florida charm and offers an ideal location just a quick stroll from the stunning white sandy beaches of the Gulf. This spacious retreat features 4 bedrooms and 3.
$3,149,000
4Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,421Sqft
More Details

110 Spring Ave, Anna Maria, Florida 34216

Residential For Sale

KW COASTAL LIVING II
Welcome to this exceptional beach retreat, an exquisite 5-bedroom, 4.5-bath luxury coastal residence steps from the sugary sands of Anna Maria Island. Completely reimagined in 2022, this elevated home blends modern coastal elegance with the island’s timeless charm—creating the ideal retreat for luxury buyers, investors, or multigenerational families seeking premium beachside living.
$3,000,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,925Sqft
More Details

418 Magnolia Ave, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Sea Vous Play is 4 bedroom, 4.5 bathroom home located on Anna Maria Island. The home has an open living, dining, and kitchen area that is perfect for hosting family meals and game nights. The kitchen features Jenn Air appliances, custom white cabinets, and a breathtaking glass backsplash.
$2,995,000
4Bedroom(s)
5Bathroom(s)
2,186Sqft
More Details

704 Gladiolus St, Anna Maria, Florida 34216

Residential For Sale

ISLAND REAL ESTATE-ANNA MARIA
You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool home with private elevator.
$2,995,000
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,415Sqft
More Details

510 Magnolia Ave, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Welcome to Aloha Beaches. This home is a successful active rental in the city of Anna Maria. It started out as a 2-bedroom, 2-bath elevated home with a loft and no pool. However, with the seller’s vision, the home was transformed by Wash Family Construction and Agnelli pools into what you see today. Today it is a gorgeous 4-bedroom 3-bath open floor plan pool home.
$2,995,000
4Bedroom(s)
3Bathroom(s)
2,225Sqft
More Details

159 Crescent Dr, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Location, location, Location. Welcome to Tropical Paradise. What more can you ask for in the City of Anna Maria? This home checks all the boxes. It is three houses and 200 steps to the calm beaches at Bayfront Park. It is an easy walk to the almost complete City Pier, the Waterfront Restaurant and all the other shops and restaurants on Pine Ave. It is the perfect home for any of your needs.
$2,995,000
4Bedroom(s)
3Bathroom(s)
2,567Sqft
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