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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107 Elm Ave, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA ISLAND BEACHES RE
Beachfront Oasis is elegant European design luxury home that has been professionally decorated and has spectacular beach views from every room. Floor to ceiling glass allows full views of the beach and aqua tropical gulf waters. The clean lines of the homes upscale design allow you to just sit back, relax and enjoy the stunning open beach view on any of the four beachfront decks.
$5,245,000
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,432Sqft
More Details

519 Villa Rosa Way, Anna Maria, Florida 34216

Residential For Sale

WAGNER REALTY
This stunning property, situated on the premier private street of Anna Maria, was designed for the perfect blend of island indoor living and outdoor entertaining. Completed in 2017, this 3385sq ft open-plan luxury home has over 2000 SQ FT OF EXTERIOR PORCHES (6 porches). The ROOFTOP LOOKOUT DECK has expansive views extending from Tampa Bay to the Gulf of Mexico beaches.
$5,000,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
3,385Sqft
More Details

222 Willow Ave, Anna Maria, Florida 34216

Residential For Sale

DUNCAN REAL ESTATE, INC.
Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable streets on Anna Maria Island. SeaLuxe is a home thats perfectly positioned to put you just a short walk away from a world-renowned beach or to Pine Ave where you can find locally owned shops and restaurants.
$4,995,000
4Bedroom(s)
6Bathroom(s)
3,265Sqft
More Details

112 Maple Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
STUNNING NEW CONSTRUCTION HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED 5 BEDROOM, 4.5 BATHROOM HOME LOCATED ON ONE OF THE PREMIER STREETS OF ANNA MARIA ISLAND!! With only 5 houses to the beach, this new construction gem is an absolute treasure.
$4,965,000
5Bedroom(s)
5Bathroom(s)
2,545Sqft
More Details

311 Spring Ave, Anna Maria, Florida 34216

Residential For Sale

ARC REALTY GROUP
Welcome to Go With The Flow, a brand-new, luxurious five-bedroom, five-and-a-half-bath retreat that blends modern opulence with a vibrant beachside charm. Designed for ultimate relaxation and entertainment, this stunning property features an unparalleled Lazy River-style pool with an in-ground spa, offering the perfect setting to bask in the radiant Florida sunshine.
$4,875,000
5Bedroom(s)
6Bathroom(s)
3,255Sqft
More Details

415 N Bay Blvd, Anna Maria, Florida 34216

Residential For Sale

WAYPOINT REAL ESTATE GROUP INC
Owner financing available with rate options as low as 3%! Welcome to Just Breathe, an opulent oasis nestled directly across from serene Bayfront Park and a short stroll from the sparkling Gulf beaches.
$4,850,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,613Sqft
More Details

112 Mangrove Ave, Anna Maria, Florida 34216

Residential For Sale

AMI REALTY GROUP
Just four houses from the beach, this stunning 4-bedroom, 4.5-bath coastal retreat by Poseidon Adventures Development Group captures the essence of Florida living. Designed for relaxation and effortless entertaining, this custom, high-performance, low-maintenance home offers exceptional comfort for both families and guests.
$4,499,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,803Sqft
More Details

870 N Shore Drive, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
LOCATION!!!! North Shore Drive, one of the most popular streets in Anna Maria! This is a gorgeous brand new custom built home with panoramic views of the Bay.
$4,450,000
4Bedroom(s)
5Bathroom(s)
2,091Sqft
More Details

513 Bayview Pl, Anna Maria, Florida 34216

Residential For Sale

SATO REAL ESTATE INC.
This Bayview Palace is a One of a kind, there’s nothing quite like this on Anna Maria Island!! Discover paradise in this 4 bedroom, 4 full bathrooms and 2 half baths, stunningly renovated home nestled in the heart of Anna Maria Island. Situated on two spacious lots, this exquisite property offers rare space, privacy, and direct access to the sparkling waters of Tampa Bay.
$4,249,000
4Bedroom(s)
6Bathroom(s)
3,464Sqft
More Details

893 N Shore Dr, Anna Maria, Florida 34216

Residential For Sale

SALTY MERMAID REAL ESTATE LLC
One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Waterfront Living on Anna Maria Island – 4BD/3BA Bayfront Home with Pool & Unmatched Views Discover your slice of coastal paradise on the prestigious north end of Anna Maria Island.
$3,990,000
4Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,933Sqft
More Details

212 Spring Ave, Anna Maria, Florida 34216

Residential For Sale

ANNA MARIA ISLAND BEACHES RE
CUSTOM BUILT HOME IS CENTRALLY LOCATED IN Anna Maria 2 BLOCKS TO THE BEACH AND ONLY A BLOCK AWAY FROM ALL THE SHOPS AND RESTAURANTS ON PINE AVE. THIS HOME WAS BUILT WITH ALL THE HOME WAS BUILT WITH ALL HIGH END FINISHES INCLUDING WOOD GRAIN TILE FLOORS, SOLID WOOD CABINETS, QUARTZ COUNTERTOPS, CUSTOM TRIM PACKAGE, VAULTED CEILINGS, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR.
$3,985,000
5Bedroom(s)
6Bathroom(s)
2,704Sqft
More Details

212 Oak Ave, Anna Maria, Florida 34216

Residential For Sale

RE/MAX ALLIANCE GROUP
STUNNING RENOVATED 5 BEDROOM POOL HOME ON A DEEP WATER CANAL ONLY STEPS FROM THE BEACH!!! Nestled on the highly coveted north end of Anna Maria Island, this beautifully renovated and turnkey furnished 5-bedroom, 5-bathroom home spans 3,844 sq. ft. of luxurious living space.
$3,950,000
5Bedroom(s)
5Bathroom(s)
3,844Sqft
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