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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!

423 Pine Avenue, Anna Maria image
423 Pine Avenue, Anna Maria $3,295,000

Pre-Construction. To be built. Pre-Construction, to be built. LUXURY LIVING at its finest in the heart of Anna Maria on historic Pine Avenue! Stunning 6 bedroom 6.5 bath...

  • 6 Beds
  • 6 Baths
  • Anna Maria Beach SubDv.
  • 34216 Zip Code
401 72nd Street, Holmes Beach image
401 72nd Street, Holmes Beach $1,949,000

This beautiful completely remodeled ground level Duplex is one of a kind on Anna Maria Island. Two amazing homes...each with 2 bedrooms with en-suites and dens with and ...

  • 4 Beds
  • 5 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
1105 Gulf Drive N, Bradenton Beach image
1105 Gulf Drive N, Bradenton Beach $2,975,000

Under Construction. ~ SOON TO BE COMPLETE! Spectacular new construction 8 Bedroom 7 1/2 Bath Luxury Beach House featuring a ROOF TOP DECK AND SPA!! Enjoy gorgeous panora...

  • 8 Beds
  • 7 Baths
  • Bay Manor Pb7/23 SubDv.
  • 34217 Zip Code
509 Pine Avenue, Anna Maria image
509 Pine Avenue, Anna Maria $1,695,000

Welcome to Naut 2 shabby Cottage - Please view the 360 virtual tours attached!. Main home features: 3 bedrooms 2 full baths, Guest House features 1 bedroom and 1 bath sep...

  • 4 Beds
  • 3 Baths
  • Anna Maria Beach SubDv.
  • 34216 Zip Code
6700 Gulf Drive Unit 15, Holmes Beach image
6700 Gulf Drive Unit 15, Holmes Beach — Gulfplace $1,150,000

Excepting back ups. Exceptionally rare to come on the market in Gulf Place, this desirable three-bedroom residence offers a lovely Gulf view and an abundance of space to ...

  • 3 Beds
  • 2 Baths
  • Gulfplace SubDv.
  • 34217 Zip Code
4001 5th Avenue, Holmes Beach image
4001 5th Avenue, Holmes Beach $1,495,000

Beautiful custom-built all concrete. Mediterranean style home 1 block away from the gorgeous beaches of Anna Maria Island! The Lot is extra large and is not leased. T...

  • 4 Beds
  • 3 Baths
  • Casanas Sub SubDv.
  • 34217 Zip Code
2206 Avenue A, Bradenton Beach image
2206 Avenue A, Bradenton Beach $2,395,000

Pre-Construction. To be built. PARADISE FOUND! NEW LUXURY BEACH HOME Soon to be UNDER CONSTRUCTION~ over 3,000 square feet of living space and 7 bedrooms! This gorgeous c...

  • 7 Beds
  • 6 Baths
  • Cortez Beach SubDv.
  • 34217 Zip Code
412 72nd Street, Holmes Beach image
412 72nd Street, Holmes Beach $1,350,000

Enjoy Island lifestyle in this 3 Bedroom 2.5 bath home in the heart of Holmes Beach. The Master Bedroom features a large bathroom with double vanity, soaking tub and walk...

  • 3 Beds
  • 2 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
4603 Gulf Drive, Holmes Beach image
4603 Gulf Drive, Holmes Beach $1,195,000

Hidden Treasure, a popular vacation rental is a beautifully renovated, 4 bedroom, and 2 bathroom single family home tucked away on Anna Maria Island with just a short 5-m...

  • 4 Beds
  • 2 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
307B 63rd Street, Holmes Beach image
307B 63rd Street, Holmes Beach $1,445,000 ▲

Casa Azul is a 3 bedroom, 3 bath, LUXURY, beach house LOCATED STEPS FROM THE BEACH and sparkling waters of the Gulf of Mexico in beautiful Holmes Beach on Anna Maria Isla...

  • 3 Beds
  • 3 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
215 Chilson Avenue, Anna Maria image
215 Chilson Avenue, Anna Maria $3,395,000 ▼

A MAJOR RENOVATION IN 2019-2020, THIS HOME IS LIKE NEW. IT CHECKS EVERY BOX! THIS LARGE 4BED/4.5 BATH 3,350 SQ FT ANNA MARIA CITY CANAL HOME SITS ON A VERY PRIVATE OVER...

  • 4 Beds
  • 4 Baths
  • Anna Maria Beach SubDv.
  • 34216 Zip Code
239 S Harbor Drive, Holmes Beach image
239 S Harbor Drive, Holmes Beach $2,249,500

New Construction!!! Coastal luxury 4 bedrooms, 4.5 baths, plus a den with a private pool/spa and spectacular views of the bay from the rooftop deck. As you walk in the fi...

  • 4 Beds
  • 4 Baths
  • Sportsmans Harbor SubDv.
  • 34217 Zip Code
211 81st Street Unit A, Holmes Beach image
211 81st Street Unit A, Holmes Beach $2,375,000

Professional photos coming soon!! New Construction in the heart of the island ~ Exquisite coastal design, luxury home featuring 4 bedrooms, 5 baths, and private pool loca...

  • 4 Beds
  • 5 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
4915 Gulf Drive, Holmes Beach image
4915 Gulf Drive, Holmes Beach $3,200,000

UNIQUE 5 UNIT BAYFRONT INCOME PROPERTY! Nestled down a quiet private drive on over a half-acre are 2 duplexes and a single family home right on the Intracoastal Waterway....

  • 3 Beds
  • 2 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
800 Jacaranda Road, Anna Maria image
800 Jacaranda Road, Anna Maria $2,895,000

North End Gem! Impeccably detailed custom beach home with an open concept that welcomes you into a luxurious island retreat. Just steps from the acclaimed oyster white sa...

  • 3 Beds
  • 2 Baths
  • Shore Acres SubDv.
  • 34216 Zip Code
6424 Gulf Drive Unit 7, Holmes Beach image
6424 Gulf Drive Unit 7, Holmes Beach — L' Plage $2,399,000

RARELY on the market! Top floor, 3 bedroom, 2.5 bathroom Gulf front condo #7 at the luxury La Plage condominiums. This unit is located in the gulf front building on the ...

  • 3 Beds
  • 2 Baths
  • L'Plage, A Condominium SubDv.
  • 34217 Zip Code
228 Willow Avenue, Anna Maria image
228 Willow Avenue, Anna Maria $3,485,000

Anna Maria living at its finest. It truly does not get better than this canal front home located on one of the most coveted streets on Anna Maria. This stunning home exud...

  • 6 Beds
  • 4 Baths
  • Bimini Bay Estates SubDv.
  • 34216 Zip Code
2508 Gulf Drive N, Bradenton Beach image
2508 Gulf Drive N, Bradenton Beach $5,875,000

Have you dreamed of waking up to the sound of crashing waves and settling in at night to the beautiful lighting of a Florida sunset? Here is your chance! Beach Side Parad...

  • 7 Beds
  • 6 Baths
  • Ilexhurst SubDv.
  • 34217 Zip Code
112 8th Street S, Bradenton Beach image
112 8th Street S, Bradenton Beach $2,495,000 ▼

Under Construction. New luxury home with amazing views located between the bay and Gulf of Mexico. This seven bedroom dream home offers high-end finishes, professional dé...

  • 7 Beds
  • 6 Baths
  • Cortez Beach SubDv.
  • 34217 Zip Code
205 S Bay Boulevard, Anna Maria image
205 S Bay Boulevard, Anna Maria $4,875,000 ▲

Blue Bay is a gorgeous custom luxury home on the northern end of Anna Maria Island that features 8 bedrooms and 6 bathrooms, fantastic views of the water and Sunshine Sky...

  • 8 Beds
  • 6 Baths
  • Anna Maria Beach SubDv.
  • 34216 Zip Code
131 White Avenue, Holmes Beach image
131 White Avenue, Holmes Beach $1,895,000 ▼

Excellent opportunity to own this elevated 5 Bedroom 4.5 Bath Pool Home West of Gulf Drive just seconds to the beach. This property is perfect for a large family island r...

  • 5 Beds
  • 4 Baths
  • Edgemere Sub SubDv.
  • 34217 Zip Code
4006 5th Avenue, Holmes Beach image
4006 5th Avenue, Holmes Beach — 4 $1,495,000

NEWLY RENOVATED 3 STORY HOME HAS IT ALL. THERE ARE 4 EN SUITE BEDROOMS, NEW FLOORING, NEW PAINT INSIDE AND OUT, REMODELED KITCHEN AND BATHS, COASTAL DECOR, S/S APPLIANCE...

  • 4 Beds
  • 4 Baths
  • 4th Avenue Condominium SubDv.
  • 34217 Zip Code
714 Jacaranda Road, Anna Maria image
714 Jacaranda Road, Anna Maria $3,950,000 ▲

Custom built 4BD/3.5BA home nestled in your private waterfront oasis at the north end of Anna Maria. From the Carriage House to the heated pool/spa, to the extra perks o...

  • 4 Beds
  • 3 Baths
  • Wells Terrace SubDv.
  • 34216 Zip Code
104 Beach Avenue, Anna Maria image
104 Beach Avenue, Anna Maria $3,700,000

"Blue Destiny", sheltered in highly sought after Banyan Tree Estates at Anna Maria's quiet north end, represents the definition of fine architecture and construction. Cu...

  • 4 Beds
  • 3 Baths
  • Anna Maria Beach SubDv.
  • 34216 Zip Code
116 50th Street, Holmes Beach image
116 50th Street, Holmes Beach $4,495,000 ▼

Luxury living at it's finest! This stunning custom built home is located on quaint Anna Maria Island and just steps from the sugar sands and crystal clear waters of the ...

  • 5 Beds
  • 6 Baths
  • Jones Sub SubDv.
  • 34217 Zip Code
118 48th Street, Holmes Beach image
118 48th Street, Holmes Beach $3,495,000

NEW COASTAL CONTEMPORARY HOME IS EVERYTHING YOU COULD WANT IN A BEACH HOUSE. THIS STUNNING 4 BED, 5.5 BATH PROPERTY IS LOCATED BEACH BLOCK WITH ONLY A 1 MINUTE WALK TO T...

  • 4 Beds
  • 5 Baths
  • Jones Sub SubDv.
  • 34217 Zip Code
305 Highland Avenue, Bradenton Beach image
305 Highland Avenue, Bradenton Beach $1,799,000

BACK ON THE MARKET AFTER BUYER'S FINANCING FELL THROUGH! Beautiful new island home. Luxury private vacation home at its finest! Beach Daze is an amazing luxury proper...

  • 7 Beds
  • 5 Baths
  • Ilexhurst SubDv.
  • 34217 Zip Code
201 72nd Street, Holmes Beach image
201 72nd Street, Holmes Beach $1,525,000 ▲

Welcome to this coastal luxury 4 bedrooms & 4 bathrooms pool duplex home centrally located on Anna Maria Island. With only steps to direct beach access and the Gulf of Me...

  • 4 Beds
  • 4 Baths
  • West Wind Shores SubDv.
  • 34217 Zip Code
108 11th Street S, Bradenton Beach image
108 11th Street S, Bradenton Beach $2,595,000 ▲

Coastal luxury ~ recently completed new construction home with amazing views located between the bay and Gulf of Mexico. This seven bedroom, dream home offers high-end fi...

  • 7 Beds
  • 7 Baths
  • Cortez Beach SubDv.
  • 34217 Zip Code
2213 Gulf Drive N, Bradenton Beach image
2213 Gulf Drive N, Bradenton Beach $1,775,000 ▼

Gorgeous, unobstructed views of the Gulf & beaches of Anna Maria Island. This spectacular 3 bedroom, 3 bath home sits across the street from a beach front park that can n...

  • 3 Beds
  • 3 Baths
  • Ilexhurst SubDv.
  • 34217 Zip Code
303 68th Street, Holmes Beach image
303 68th Street, Holmes Beach $1,695,000 ▲

LOCATED IN THE HEART OF HOLMES BEACH! This 4/3 home is a perfect family beach getaway! With vaulted ceilings and an open floor plan, this home feels bright and beachy! Fe...

  • 4 Beds
  • 3 Baths
  • Holmes Beach SubDv.
  • 34217 Zip Code
2500 Gulf Drive N, Bradenton Beach image
2500 Gulf Drive N, Bradenton Beach $4,499,000 ▼

Newly renovated luxury walkout gulf front home on beautiful Anna Maria Island. Enjoy the gulf breezes and nightly sunsets from multiple gulf front balconies. This home is...

  • 5 Beds
  • 5 Baths
  • Ilexhurst SubDv.
  • 34217 Zip Code
317 Iris Street, Anna Maria image
317 Iris Street, Anna Maria $3,700,000 ▼

Sophisticated custom home designed by the notable and highly admired architect, Gene Aubry. Behold the beauty of conceptual design to culmination here: http://listing.nob...

  • 5 Beds
  • 5 Baths
  • Luana Isles SubDv.
  • 34216 Zip Code
107 66th Street Unit 12, Holmes Beach image
107 66th Street Unit 12, Holmes Beach — 2 $848,888 ▼

Welcome to island living. This huge three-bedroom townhome has a space that can be used as another living area or turned in to a fourth bedroom. Step out on the top deck ...

  • 3 Beds
  • 3 Baths
  • Mainsail Beach Inn A Condo SubDv.
  • 34217 Zip Code
6420 Gulf Drive Unit 3, Holmes Beach image
6420 Gulf Drive Unit 3, Holmes Beach — 3 $1,349,000 ▼

You will love this delightful and spacious island condominium situated right on the Gulf of Mexico. This turnkey 3-bedroom, 3-bathroom condo has all of the amenities and ...

  • 3 Beds
  • 3 Baths
  • L'Plage, A Condominium SubDv.
  • 34217 Zip Code
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  • Anna Maria
  • Holmes Beach
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Most Popular Searches in Holmes Beach & Bradenton Beach

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Anna Maria Real Estate Types

  • Anna Maria Beach Homes
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Holmes Beach and Bradenton Beach Real Estate Types

  • Holmes Beach and Bradenton Beach Beach Homes
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What To Do On The Island

  • Biking on Anna Maria Island
  • Kayaking on Anna Maria Island
  • Shelling on Anna Maria Island
  • Paddle Boarding on Anna Maria Island
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  • Places to Visit on Anna Maria Island

 

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Billi Gartman | Realtor
ANNA MARIA LIFE

941-545-8877

    314 Pine Ave, Anna Maria, Florida, 34216

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