Anna Maria Island
Vacation and Investment Homes
Anna Maria Island is the perfect place to own
a vacation home or investment property!
Our little slice of paradise is counted as one of the most popular beach destinations in the Country every year, which makes it the ideal location for a successful investment home.
Anna Maria Island properties are increasing in value exponentially over time. Many who were not ready to make the move to the island full time have instead purchased an Investment Vacation home to enjoy throughout the year. They've placed their home with a great vacation home management company to take care of all of the details. Later, when the time comes to make their move to the island permanent, they can either move into their Anna Maria Island home full time, or sell it at have enough to purchase the perfect property for them to live in year round!
You can turn a small gulf front house into a stunning paradise cottage or a single family home into the vacation home of people’s dreams. Another great thing about investing in a real estate property on Anna Maria Island is that you can use it as a home away from home on the weeks it’s not rented!
Learn More:
Click Here to learn about why you should consider an Anna Maria Island Investment Home?
Click HERE to learn about the the top 5 things to look for in an Anna Maria Island investment vacation home!
The latest Listings of Vacation & Investment Properties for Sale on Anna Maria Island!
Gorgeous, custom-built home on the desirable North End of Anna Maria Island. This luxury 4 bedroom, 4 ½ bathroom home is only 1 1/2 blocks away from both the Gulf of Mexi...
- 4 Beds
- 4.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
This Old world charming beach cottage is located Downtown Anna Maria Right in the middle of all the activity. Very Busy Vacation rental- This Island cottage is super busy...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Under Construction. Check Florida Lifestyle off of your bucket list. This property is true Island Living with coastal charm and elegance as well as attention to detail ar...
- 4 Beds
- 4.5 Baths
- Sportsmans Harbor SubDv.
- 34217 Zip Code
Pure paradise awaits at this beautiful BRAND-NEW CONSTRUCTION built by Eason Building Group, 9-bedroom, 11-bathroom home that is just a 60 second walk from the serene coa...
- 9 Beds
- 9.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
This beautiful Anna Maria Island home radiates coastal and salty vibes! Custom designed By Emily Ann Smith, this 4 Bedroom, 4.5 Bathroom, plus bonus loft, home is locate...
- 4 Beds
- 4.5 Baths
- Gulf View Sub SubDv.
- 34216 Zip Code
Welcome home to this newly renovated 3BD/2BA island home just 1 block to the Gulf of Mexico! Vaulted ceilings, open floor plan and tastefully updated kitchen perfect for ...
- 3 Beds
- 2 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Are you ready to just CHECK OUT… live on a TROPICAL ISLAND and never have to leave? This is the answer! The highly revered NORTHERN tip of ANNA MARIA Island offers the l...
- 3 Beds
- 3 Baths
- Lake La Vista Sub SubDv.
- 34216 Zip Code
This 3 bedroom, 2 bathroom home is nestled along a canal on the north end of Anna Maria Island. This secluded treasure embodies Florida living at its finest. Spacious 1,...
- 3 Beds
- 2 Baths
- Luana Isles SubDv.
- 34216 Zip Code
TWO PROPERTIES sitting directly on the Gulf of Mexico Beaches in Holmes Beach!! Both properties just had a refresh, including paint exterior and interior and new decorati...
- 5 Beds
- 4 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Under Construction. This UNIQUE AND EXTRAORDINARY custom home will have all the amenities that you can ever dream of in a beach house. This Stunning home will feature 5 B...
- 5 Beds
- 5.5 Baths
- Arroyo The SubDv.
- 34216 Zip Code
This is a beautifully appointed single story half duplex located just a stroll away from the sandy beaches and the Gulf of Mexico. Shops, bars and restaurants are also cl...
- 3 Beds
- 2 Baths
- Bay Palms SubDv.
- 34217 Zip Code
Under Construction. Under Construction....Stunning new build just a block from the pearly sands of the Gulf! This unique, contemporary home will be showstopper...complete...
- 4 Beds
- 4.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
Under Construction. Contemporary design meets waterfront luxury in this Brand-New Construction home built in the heart of Bradenton Beach on Anna Maria Island. Exquisite ...
- 6 Beds
- 6.5 Baths
- Cortez Beach SubDv.
- 34217 Zip Code
100 YARDS TO THE BEACH, Anna Maria Island BAYFRONT townhome - phenomenal, panoramic bay VIEWS of Anna Maria Sound and partial Gulf of Mexico VIEWS! Bermuda Bay Club is a ...
- 3 Beds
- 2.5 Baths
- Bermuda Bay Club SubDv.
- 34217 Zip Code
Step in to Limelight. This beautifully appointed, furnished 3BD/2BA residence is located on the north end of Anna Maria with a direct beach access steps away. Let the nat...
- 3 Beds
- 2 Baths
- Shore Acres Second Add SubDv.
- 34216 Zip Code
Welcome to Paradise at Harbor Side, a wonderful 5 Bedroom, 3.5 Bathroom waterfront property located in a prime location in Holmes Beach. Step outside your front door and...
- 5 Beds
- 3.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
COASTAL BEAUTY IS WEST OF GULF AND A BLOCK TO THE BEACH. THIS CUSTOM HOME HAS SOLID WOOD CABINETS, SOLID GRANITE SURFACES, TILE FLOORS, S/S APPLIANCES AND COMES TURNKEY ...
- 5 Beds
- 4.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Welcome to Mango Tango! This Anna Maria Island beach home is 4 bedrooms and 3.5 bathrooms and is so close to the Gulf of Mexico beaches! This is currently a vacation rent...
- 4 Beds
- 3.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
GREAT COASTAL HOME ON N SHORE DRIVE IS RIGHT ACROSS THE STREET FROM THE BEACH. THIS CUSTOM HOME WAS BUILT WITH HIGH END FINISHES INSIDE AND OUT. INSIDE IS SOLID WOOD CA...
- 5 Beds
- 4.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Nice price adjustment! Enjoy living the relaxed Anna Maria lifestyle on your canal front home that is one and a half blocks to the Gulf of Mexico. 90ft water frontage ho...
- 3 Beds
- 2 Baths
- Laguna Maria SubDv.
- 34216 Zip Code
Welcome to this beautifully appointed 4BD/3.5 bath home in a central island location. The main living area offers lots of natural light, crown moldings, open living/dinin...
- 4 Beds
- 3.5 Baths
- Clark & Palm SubDv.
- 34217 Zip Code
The magic of Anna Maria Island is embraced throughout this newly built home while affording maximum return on investment with short-term, weekly rental opportunities to p...
- 4 Beds
- 4.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
Pre-Construction. To be built. Pre-Construction. To Be Built. Luxury 6 bedroom 6.5 bathroom NEW CONSTRUCTION home will have all the amenities you could EVER ASK FOR in a ...
- 6 Beds
- 6.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. ISLAND LIVING AT ITS BEST! This stunning home will feature 7 BEDROOMS AND 7 BATHROOMS with no expense spared...
- 7 Beds
- 7 Baths
- Bimini Bay Colony Club Sub SubDv.
- 34216 Zip Code
Under Construction. PHOTOS USED ARE OF A SIMILAR LISTING. Experience a luxury vacation. The future 6 bedroom, 6 bathroom and 1 half bath is located in the heart of Anna M...
- 6 Beds
- 6.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Life on Anna Maria is truly close to paradise, and this home sits right in the heart of all of the unique and beautiful elements of this amazing island. From beautiful su...
- 3 Beds
- 2 Baths
- Bay Palms SubDv.
- 34217 Zip Code
Welcome to "Grand Island Oasis" Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Lo...
- 8 Beds
- 5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Under Construction. Under construction..To be completed. This stunning new build by Eason Builder's Group will be a show stopper! Located on the North end of Anna Maria o...
- 6 Beds
- 6.5 Baths
- Gulf View Sub SubDv.
- 34216 Zip Code
Welcome to "Casa Azul" a 3 bedroom, 3 bath, luxury beach house located 600 steps from the beach in beautiful Holmes Beach on Anna Maria Island. Offered TURN KEY furnished...
- 3 Beds
- 3 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Welcome to paradise! Newly updated, this 3 bedroom, 2 bathroom is perfect for living island style! Located off popular Marina Drive in the heart of Holmes Beach on Anna...
- 3 Beds
- 2 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Welcome to The Jersey Girl, a popular vacation rental on the North End of Anna Maria Island! Perfectly located just 3.5 blocks away from the Gulf of Mexico Beaches while ...
- 5 Beds
- 3 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Welcome to luxury coastal living on Anna Maria Island! This gorgeous island retreat is only one block away from pristine powder sand and stunning turquoise water beaches....
- 4 Beds
- 4.5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Welcome to “Blue Lagoon”, a resort-style new construction home on Anna Maria’s prestigious north end. Beautifully situated on an extremely large lot (over 12,000 sq ft), ...
- 4 Beds
- 4.5 Baths
- Bay Harbor Subdivision SubDv.
- 34216 Zip Code
Welcome to luxury coastal living on Anna Maria Island! This gorgeous multi-level home, built in 2021, has 4 bedrooms, 5.5 baths, plus den and a private pool and spa! Enj...
- 4 Beds
- 5.5 Baths
- Sportsmans Harbor Rev SubDv.
- 34217 Zip Code
Pre-Construction. To be built. Welcome to 215 82nd Street, right in the heart of pristine island living. 3-story luxury residence designed by elite team of architects and...
- 4 Beds
- 5.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Welcome to your new 3-bedroom, 3-bathroom beach house! This spectacular home is a timeless paradise treasure situated in the heart of Bradenton Beach. This home has been...
- 3 Beds
- 3 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Back on the Market! Welcome to this luxury retreat located on Anna Maria Island! This newly renovated 4 bedroom 3 bathroom pool home features a residents only boat ramp w...
- 4 Beds
- 3 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
BEAUTIFUL COASTAL HOME ONLY STEPS AWAY FROM THE PRISTINE BEACHES ON BEAN POINT. THIS 4 BEDROOM 2.5 BATH HAS QUALITY FINISHES THROUGHOUT INCLUDING SOLID GRANITE SURFACES,...
- 4 Beds
- 2.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Welcome to paradise!! Newly built in 2014. Come to Anna Maria Island and stay forever. Furnished vacation rental or make it your primary home. This unique style duplex fe...
- 3 Beds
- 2 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
4 Bedroom, 2 Bath house in the heart of Holmes Beach. TILE FLOORING throughout. Short peaceful and sunny 100-step stroll to the Gulf of Mexico and our flour soft, sugar s...
- 4 Beds
- 2 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Under Construction. Magnificent NEW CONSTRUCTION home in the heart of Anna Maria and only two blocks to the crystal-clear waters of the Gulf of Mexico. This exquisite bui...
- 5 Beds
- 5.5 Baths
- Coconut Ave SubDv.
- 34216 Zip Code
One or more photo(s) has been virtually staged. DO NOT MISS THIS RARE OPPORTUNITY...Looking for your dream home with amazing Gulf of Mexico views or a one-in-a-million op...
- 5 Beds
- 5.5 Baths
- Azure Shores SubDv.
- 34217 Zip Code
If you’ve ever wanted a Beach House on Anna Maria Island this bright and cheerful house in the center of Anna Maria Island is the one for you. Two short blocks to the lux...
- 3 Beds
- 2 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
*** PRICE REDUCTION *** Your new Anna Maria Cottage is calling your name. Welcome to 155 Crescent Dr. A very special location on the preferred north end of Anna Maria, ye...
- 3 Beds
- 2 Baths
- Lake La Vista Sub SubDv.
- 34216 Zip Code
This fully furnished 3 bed/2 bath custom canal front home on deep sailboat water, has no bridges to the bay, and is located on a quiet cul-de-sac, overlooking mangroves w...
- 3 Beds
- 2 Baths
- Wells Bay Harbor SubDv.
- 34216 Zip Code
This sleek, modern newly custom built 3 bedroom, 2 bathroom pool home is ideally located directly across the street from Anna Maria City's Bayfront park. The main level ...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
BEAUTIFUL CUSTOM HOME WEST OF GULF IN Anna Maria HAS IT ALL. THERE ARE GREAT FEATURES INSIDE AND OUT. INSIDE THERE ARE SOLID WOOD CABINETS, QUARTS COUNTERTOPS, WOOD LOO...
- 4 Beds
- 4.5 Baths
- Gulf View Sub SubDv.
- 34216 Zip Code
AMAZING COASTAL HOME IS ONLY A BLOCK TO THE WHITE SANDY BEACHES OF ANNA MARIA ISLAND. THIS COASTAL BEAUTY HAS BEEN BEAUTIFULLY MAINTAINED AND HAS GREAT FEATURES INSIDE A...
- 4 Beds
- 3.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
BACK ON THE MARKET - PRICE REDUCTION - Welcome to "Hidden Treasure" - Built in 2019 this luxury canal front home features 7 bedrooms with 7.5 bathrooms all en-suite, maki...
- 7 Beds
- 7.5 Baths
- Bayview Of Bradenton Beach Con SubDv.
- 34217 Zip Code
LOWEST $/SQFT ELEVATED SINGLE FAMILY HOME IN Bradenton Beach IS A GREAT CUSTOM BUILT HOME AND HAS GREAT FEATURES INSIDE AND OUT. INSIDE THERE ARE 5 BEDS AND 4 BATHS, ENG...
- 5 Beds
- 4 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Completely updated & turnkey! Stunning 4 bedroom 4 bath luxury duplex pool home just 1 block from the beach! Newer heated salt water pool & backyard is a private oasi...
- 4 Beds
- 4 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
Spacious Fully furnished and ready to move in. A perfect spot to work from your new home or a great vacation rental. High speed internet and excellent cell service. This...
- 4 Beds
- 4 Baths
- Island Cedars SubDv.
- 34216 Zip Code
In the heart of The City of Anna Maria directly on historic Pine Ave just 2 blocks to the beach! This 3 bedroom 2 Bath property is a wonderful island getaway and rental i...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
It's Blue-ti-ful! This gorgeous 4 bedroom, 3 bath home is located in one of the prime neighborhoods near the North End of Anna Maria Island. NEWLY refreshed with coastal...
- 4 Beds
- 3 Baths
- Lake La Vista Sub SubDv.
- 34216 Zip Code
Full of Florida Charm and Recently Restored. Welcome to Buttonwood Cottage situated in the heart of Anna Maria Island on the Famous Pine Avenue. Every corner of this gorg...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Coastal construction 5-bedroom home with 3.5 baths with stunning views of the Gulf of Mexico from the second and third living levels, but especially from the roof top dec...
- 5 Beds
- 3.5 Baths
- Azure Shores SubDv.
- 34217 Zip Code
MOTIVATED SELLER SAYS "BRING OFFERS" NEW PRICE AND UPDATES! One-of-a-kind CANAL FRONT home on an estate sized parcel of 13,200 sq ft, located on highly desirable N...
- 3 Beds
- 3 Baths
- Island Cedars SubDv.
- 34216 Zip Code
Welcome to "Absolute Paradise" at 217 Magnolia Ave! This wonderful property that features 5 Bedrooms and 4 Bathrooms, a private tropical pool and spa, covered patio and m...
- 5 Beds
- 4 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Luxury Island living at its finest! You simply will not find another property like it on AMI, with many features that are no longer available for construction in Holmes ...
- 6 Beds
- 6.5 Baths
- Jones Sub SubDv.
- 34217 Zip Code
AMAZING ISLAND HOME IN THE HEART OF ANNA MARIA. THIS IS A CUSTOM BUILT 2000 SQUARE FOOT 5 BEDROOM, 3 AND ONE HALF BATH WITH HIGH END FINISHES. THIS HOME IS ONLY A BLOCK ...
- 5 Beds
- 3.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
This beautiful home is located right in the heart of Anna Maria Island and borders the island's only true lake. This 3 story home was finished in November 2015 and has 3 ...
- 3 Beds
- 3.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Beach House Paradise! Open the front door, take in the sea breeze, take a look to the side and start walking - 600 steps to the Beach on Anna Maria Island where Summer l...
- 3 Beds
- 2.5 Baths
- Gulf Breeze Condominium SubDv.
- 34217 Zip Code
Welcome to AMI Oasis A spectacular 4 bedroom, 4..5 home located in the most desired area of the North End of Anna Maria Island. The location has the best of both worlds o...
- 4 Beds
- 4.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
A GREAT INVESTMENT PROPERTY ON ANNA MARIA ISLAND WITH $235K PER YEAR IN GROSS RENTAL INCOME. THIS LARGE RENTAL HOME IS LESS THAN THREE BLOCKS TO THE WORLD FAMOUS BEACHE...
- 6 Beds
- 4.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Blue Bay is an upscale, luxury home that offers the desirable north end location on Anna Maria Island, high-end finishes, unique layout that includes a guest house, a res...
- 8 Beds
- 6 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Under Construction. BRAND NEW CONSTRUCTION AT THE GULF OF MEXICO BY PREMIER, WELL RESPECTED BUILDER WHITEHEAD CONSTRUCTION. Soaring Gulf Views, Volume Ceilings, Open Floo...
- 4 Beds
- 4 Baths
- Holmes Beach SubDv.
- 34217 Zip Code