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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136 Crescent Dr, Anna Maria, Florida 34216

Residential For Sale

ISLAND REAL ESTATE-ANNA MARIA
Anna Maria Island charming remodeled coastal cottage. Now is the time for new owners to make 136 Crescent Dr their own island oasis. Whether you are looking or a primary residence, second home or investment property this home is an ideal opportunity. Located in the quiet and serene City of Anna Maria on the north end where short term rentals are welcome.
$1,249,000
2Bedroom(s)
2Bathroom(s)
DrivewayParking(s)
1,068Sqft
More Details

527 Bayview Pl, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Discover the potential of this two-bedroom, two-bathroom home situated on a generous 6,500 sqft lot. While the property experienced flood damage from Hurricane Helene, all drywall and insulation have been promptly removed, offering a blank canvas for your vision.
$1,200,000
2Bedroom(s)
2Bathroom(s)
1,246Sqft
More Details

259 Gladiolus St, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
Discover the charm of true island living with this WATERFRONT home on the coveted north end of Anna Maria Island. Perfectly positioned on an expansive 10,000+ sq ft lot, this property offers exceptional space, privacy, and endless potential to create your dream coastal retreat.
$1,050,000
2Bedroom(s)
2Bathroom(s)
1,675Sqft
More Details

216 Archer Way, Anna Maria, Florida 34216

Residential For Sale

ISLAND REAL ESTATE-ANNA MARIA
Under contract-accepting backup offers. Opportunity knocks at Anna Maria Island's much desired North End. This 3 bedroom/2 bath home, although damaged in Hurricane Helene, is structurally sound and situated in an ideal location on a quiet street on a 7,784 square foot lot - within easy walking distance to the sugar sand Gulf Beaches and the shops and restaurants that define Pine Avenue.
$895,000
3Bedroom(s)
2Bathroom(s)
DrivewayParking(s)
1,020Sqft
More Details

522 Pine Ave #7d, Anna Maria, Florida 34216

Residential For Sale

MICHAEL SAUNDERS & COMPANY
“Sittin’ on the dock of the Bay…” Welcome to your peaceful island retreat—a charming elevated 2-bedroom, 1-bath condo with its own deeded boat slip and incredible access to Tampa Bay—just minutes to open water. Nestled along a tranquil canal, this cozy getaway invites you to relax on your private back patio as manatees drift by and seabirds call in the distance.
$565,000
2Bedroom(s)
1Bathroom(s)
822Sqft
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522 Pine Ave #8b, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
Welcome to your slice of paradise on the north end of Anna Maria Island! One of the most desirable AND currently most affordable WATERFRONT condos located on beloved Pine Avenue. No detail was missed, this lovely light filled 2-bedroom, 1-bath unit has been beautifully renovated and offers the perfect blend of modern comfort and island charm.
$559,990
2Bedroom(s)
1Bathroom(s)
822Sqft
More Details

522 Pine Ave #6b, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
This is your chance to fall in love with this hidden gem - 2 bedroom, 1 bathroom WATERFRONT condo is on the ground floor and is located in the Bayou, Anna Maria City's only condo complex. In the heart of Anna Maria, yet tucked back off of bustling Pine Avenue, enjoy peace and quiet while still being steps away from many shops, restaurants, and white sand beaches.
$549,000
2Bedroom(s)
1Bathroom(s)
AssignedParking(s)
822Sqft
More Details

522 Pine Ave #1a, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
LOCATION! Welcome to island living at its finest in this newly renovated, turnkey furnished 2-bedroom, 1-bath condo located on highly desirable Pine Avenue. This serene first-floor corner unit offers privacy, and direct canal views from the spacious living room and dining nook or right from your outdoor patio.
$545,000
2Bedroom(s)
1Bathroom(s)
822Sqft
More Details

522 Pine Ave #6a, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA LIFE REAL ESTATE
Life’s better on island time—especially when you can own a waterfront condo in the coveted city of Anna Maria at a price this rare! Dreaming of island life? This is your chance. Tucked away on the water just steps from the sugar-sand beaches, local shops, and breezy restaurants of Anna Maria Island, this 2-bedroom, 1-bath condo is the kind of opportunity that doesn’t come around often.
$475,000
2Bedroom(s)
1Bathroom(s)
AssignedParking(s)
822Sqft
More Details

306 N Shore Drive #A, Anna Maria, Florida 34216

Residential Lease For Rent

DUNCAN REAL ESTATE, INC.
Annual rental on the North end of the Island. 2 bedroom 1 bath. Great old Florida style duplex with lots of wood and travertine flooring thru-out. Tall ceilings in all the rooms. Large lanai overlooking the canal in the rear. Great location walk to the beach and shopping on Pine Ave. Immediate occupancy with application approval. Non-smoking and no pets allowed.
$2,500
2Bedroom(s)
1Bathroom(s)
900Sqft
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