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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769 North Shore Dr, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
Pre-Construction. To be built. Luxurious Beachfront Oasis in Anna Maria, Florida. Experience coastal living at its finest in this brand-new, 7,652 sq ft beachfront estate located in the heart of Anna Maria. This stunning home features 6 spacious bedrooms and 6 elegantly designed bathrooms, including a separate mother-in-law suite complete with a great room, bedroom, bathroom, and powder room.
$20,000,000
6Bedroom(s)
9Bathroom(s)
Garage Door OpenerParking(s)
7,652Sqft
More Details

801 N Shore Dr, Anna Maria, Florida 34216

Residential For Sale

COMPASS FLORIDA LLC
Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless Gulf-front residence that blends enduring craftsmanship with inspired artistry. Thoughtfully curated and offered turnkey furnished, this extraordinary home is appointed with bespoke furnishings and window treatments by Italian artisans, complemented by world-renowned works of art that elevate every space.
$10,950,000
3Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,728Sqft
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832 S Bay Blvd #a & B, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Exquisite Bayfront Estate with a Main House and a Guest House! Experience unparalleled luxury on the pristine Anna Maria Island at this magnificent bayfront compound. Featuring a spacious main house with 6 bedrooms and 6.
$9,000,000
11Bedroom(s)
12Bathroom(s)
5,591Sqft
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9403 Gulf Dr, Anna Maria, Florida 34216

Residential For Sale

DEVELOPERS REALTY LBK, INC
This stunning 9-bedroom, 8.5-bathroom beachfront property offers 3,983 sq ft of heated interior space and comes FULLY FURNISHED with luxurious details throughout. The home boasts an open-concept layout with vibrant living areas, a well-appointed chef’s kitchen, and multiple decks for enjoying ocean views.
$8,000,000
9Bedroom(s)
9Bathroom(s)
3,983Sqft
More Details

9407 Gulf Dr, Anna Maria, Florida 34216

Residential For Sale

DEVELOPERS REALTY LBK, INC
Located on picturesque Anna Maria Island, this exceptional 9-bedroom, 8.5-bathroom coastal retreat offers 4,244 sq ft of heated living space with luxurious amenities throughout. The open-concept interior features an oversized kitchen with a spacious quartz island, upgraded appliances, and a wet bar for entertaining.
$8,000,000
9Bedroom(s)
9Bathroom(s)
4,244Sqft
More Details

242 Oak Ave, Anna Maria, Florida 34216

Residential For Sale

MICHAEL SAUNDERS & COMPANY
January 2025 SPECIAL...Buyer to pay all 2026 Property Taxes for any accepted contract by January 30, 2025. Over $50,000 value.  Your luxury island estate is ready to preview now. Welcome to Ami Dream Home. Step into effortless luxury at this impeccably turnkey furnished waterfront estate, fully ready for the Winter 2025-2026 season. Every detail has been curated for seamless island living.
$7,999,000
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,722Sqft
More Details

107 Maple Ave, Anna Maria, Florida 34216

Residential For Sale

ARC REALTY GROUP
This turn-key custom built six bedroom six and a half bathroom luxury home on Anna Maria Island is an exceptional beach investment property offering the perfect balance of passive rental income and personal coastal living.
$7,500,000
6Bedroom(s)
7Bathroom(s)
6,500Sqft
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229 Willow Ave, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
Here is your chance to own a 5 bed/4.5 bath custom waterfront residence on one of the most coveted streets in the City of Anna Maria. Enjoy the rare luxury of having direct boat access in your backyard while just a short walk to the pristine shores of the Gulf. This home offers the best of both waterfront lifestyles.
$6,375,000
5Bedroom(s)
5Bathroom(s)
3,250Sqft
More Details

403 N Shore Dr, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Discover unparalleled elegance in this stunning 3,400 sq. ft. very private residence 5 houses away from the Gulf on the north end of Anna Maria Island! You get to enjoy beach views from many rooms in the house without the beachfront price! Very well taken care of, never rented, and hurricane-rated elevated home that stands at one of the island’s highest elevation points.
$5,995,000
5Bedroom(s)
7Bathroom(s)
3,400Sqft
More Details

244 Willow Ave, Anna Maria, Florida 34216

Residential For Sale

AMI REALTY GROUP
Breathtaking 6-bedroom, 6-bathroom canal-front estate on the picturesque Anna Maria Island. This extraordinary coastal retreat epitomizes modern luxury, seamlessly blending sophisticated design, resort-style amenities, and island charm. From the moment you step inside, soaring ceilings, an expansive open floor plan, and an abundance of natural light create an inviting and airy ambiance.
$5,799,900
6Bedroom(s)
7Bathroom(s)
3,695Sqft
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404 North Shore Dr, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA ISLAND BEACHES RE
This recently constructed home on Anna Maria Island overlooking a stunning canal is just one block from the pristine Gulf of Mexico beaches and a short walk to the restaurants and boutiques on Pine Ave. This luxurious 5-bedroom, 5.
$5,790,000
5Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
3,159Sqft
More Details

329 Tarpon St, Anna Maria, Florida 34216

Residential For Sale

COLDWELL BANKER REALTY
Experience the charm of Anna Maria Island with this NEWLY COMPLETED CONSTRUCTION. This luxurious home boasts four bedrooms and four and a half baths, offering STUNNING VIEWS. Features include an elevator, a three-car garage, and 3,751 square feet of air-conditioned space, and 7,893 square feet overall.
$5,775,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
3,751.17Sqft
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