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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509 Pine Ave #a, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Income-Producing Property or Commercial Opportunity – Prime Pine Avenue Location! Attention investors and business-minded buyers! 509 Pine Avenue offers a rare chance to own a dual-zoned (residential/commercial) property in the heart of Anna Maria Island — ideal for those seeking immediate rental income, a business location, or the flexibility to do both.
$2,500,000
4Bedroom(s)
3Bathroom(s)
2,187Sqft
More Details

733 Holly Rd, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Welcome to Summer Breeze - A rare island gem tucked away on Anna Maria’s coveted North End! This elevated 5-bedroom, 4-bath coastal retreat sits on an oversized corner ¼-acre lot surrounded by lush tropical landscaping, just steps from the world-famous Bean Point beach. Whether you're seeking the ultimate family getaway or a high-performing investment property, Summer Breeze delivers.
$2,500,000
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,838Sqft
More Details

526 Loquat Dr, Anna Maria, Florida 34216

Residential For Sale

AN ISLAND PLACE REALTY INC
You have to see this home to appreciate the efficient layout and spacious living spaces. This property comes turnkey furnished, making it a seamless transition for the fortunate new owners. Meticulously maintained and never rented, the home exudes a sense of care and pride. For those considering short-term rentals, this residence presents an attractive opportunity.
$2,450,000
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,608Sqft
More Details

616 Fern St, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Under contract-accepting backup offers. THIS is PARADISE! Enjoy this like-new construction beautiful 3 bedroom, 3 bathroom multi-leveled home. Nestled on the north end of Anna Maria Island just steps away from the sparkling waters of the Gulf and Bay as well as close to Pine Ave! Enjoy the natural sunlight open concept and the professionally decorated interior design.
$2,425,000
3Bedroom(s)
3Bathroom(s)
2,156Sqft
More Details

311 Iris St, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
Under contract-accepting backup offers. Surrounded by lush tropical beauty on the north end of Anna Maria Island, this lovingly maintained canal front home invites you to embrace island living with both style and ease.
$2,350,000
3Bedroom(s)
2Bathroom(s)
2,233Sqft
More Details

401 N Shore Dr, Anna Maria, Florida 34216

Residential For Sale

NDC REALTY, LLC
Stunning Fully Remodeled 3-Bedroom Home with Pool & Spa – Prime North End Location. Welcome to your dream coastal retreat! This beautifully remodeled 3-bedroom, 2-bath home was completely transformed in the spring of 2025 and professionally decorated with designer furnishings. Since the renovation, the home has never been occupied—offering a truly brand-new interior experience.
$2,200,000
3Bedroom(s)
2Bathroom(s)
1,680Sqft
More Details

527 Magnolia Ave, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom, 2-bathroom waterfront retreat offers the perfect blend of coastal elegance and island convenience. Being sold turnkey with a strong rental history and bookings in place, this property is an ideal investment opportunity or full-time residence.
$2,195,000
3Bedroom(s)
2Bathroom(s)
CoveredParking(s)
1,924Sqft
More Details

307 Spring Ave, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA LIFE REAL ESTATE
~~~~~ READY.....SET..... HERE'S YOUR DEAL! ~~~~~ Come take a look at this amazing Anna Maria home. Villa Maria is ready for you! An amazing 3 bedroom, 2 bathroom and a half bath just 2.5 blocks away from some of the most coveted beaches in the country. This popular vacation rental is perfectly nestled in the city of Anna Maria.
$2,125,000
3Bedroom(s)
3Bathroom(s)
1,968Sqft
More Details

785 Jacaranda Rd, Anna Maria, Florida 34216

Residential For Sale

ISLAND REAL ESTATE-ANNA MARIA
OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to enjoy about this great investment home! This is the perfect beach haven, just a hop, skip & a jump to the Gulf beach! Just steps to Bean Point, this elevated 3 bed/2.5 bath pool home is a great income property! Updated with beautiful coastal style, this home is designed for relaxing.
$1,999,900
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
1,500Sqft
More Details

312 Hardin Ave, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA LIFE REAL ESTATE
WELCOME to Bimini Bay – Your Oasis Awaits! Step into your dream getaway at Bimini Bay, where this stunning home offers everything you need for the perfect beach house in paradise. Ideal for both vacationers and renters alike, this four-bedroom, three-bathroom retreat is nestled in the charming heart of Anna Maria.
$1,999,500
4Bedroom(s)
3Bathroom(s)
1,843Sqft
More Details

411 Alamanda Rd, Anna Maria, Florida 34216

Residential Income For Sale

SATO REAL ESTATE INC.
Incredible opportunity on the North end of Anna Maria Island. Located in the heart of the city of Anna Maria. Short walks to the Gulf or Bay beaches and all of the lovely attractions on Pine Avenue. Currently on the massive, lots 3&4, 11,500 square foot lot sits two duplex units.
$1,900,000
8Bedroom(s)
4Bathroom(s)
2,880Sqft
More Details

110 Palmetto Ave, Anna Maria, Florida 34216

Residential For Sale

ISLAND REAL ESTATE-ANNA MARIA
Under contract-accepting backup offers. Prime location at Anna Maria's north end. West of Gulf Drive and only 3 houses to the Gulf. Home was hurricane damaged and being sold for lot value.
$1,850,000
1Bedroom(s)
1Bathroom(s)
596Sqft
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