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!
Situated on a corner lot this 6BD/5BA furnished residence checks all the boxes. The foyer entry leads to the great room with lots of living space, dining nook, open kitch...
- 6 Beds
- 5 Baths
- Bay Palms Add SubDv.
- 34217 Zip Code
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. Walkable to area attractio...
- 3 Beds
- 2 Baths
- Lake La Vista Sub SubDv.
- 34216 Zip Code
Incomparable views of Bimini Bay from this one-of-a-kind property positioined in one of the most desirable waterfront locations on beautiful Anna Maria Island. Build your...
- 4 Beds
- 3 Baths
- Bimini Bay Estates SubDv.
- 34216 Zip Code
Dreaming of azure tides out your back door? This charming beach bungalow is located directly on the beautiful sand in Holmes Beach. Enjoy the sounds of the waves from The...
- 4 Beds
- 3.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
This gorgeous mid century modern home is truly something out of your wildest dreams! This showstopper is over 5,000 square feet of living space, designed by an award winn...
- 7 Beds
- 3 Baths
- Shore Acres SubDv.
- 34216 Zip Code
Come see Pineapple Paradise! This exceptional coastal cottage is only steps to the beach and ready for you to enjoy all the designer updates this home has to offer. The k...
- 4 Beds
- 6.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
If you are looking for a home that's fits the whole family, this is it! This amazing income producing property is one of the few 8-bedroom homes built on the island and h...
- 8 Beds
- 5.5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Island living at it's finest! This stunning coastal home features 5 bedrooms and 6.5 baths and is designed with exquisite touches throughout. The home features wood grain...
- 5 Beds
- 6.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
This beautifully appointed 6 bedroom 4.5 bathroom luxury beach house is just steps away from the sugary soft sandy beaches. This navy blue stunner is settled in the middl...
- 6 Beds
- 4.5 Baths
- West Wind Shores SubDv.
- 34217 Zip Code
This luxury island home beautifully boasts 6 bedrooms, and 5 bathrooms. With 11 foot ceilings in the kitchen and living area, plus an outdoor backyard pool area complete ...
- 6 Beds
- 5.5 Baths
- Gulf View Sub SubDv.
- 34217 Zip Code
Welcome to Happy Ourz in Paradise Village on Anna Maria Island, where coastal charm and exceptional privacy create a blissful retreat. Experience the quintessential islan...
- 3 Beds
- 2 Baths
- Lindo Vista SubDv.
- 34217 Zip Code
Under Construction. LOCATION, LOCATION, LOCATION! This brand-new home with estimated completion date of August 2022 has everything you're looking for in a luxury home. ...
- 7 Beds
- 6.5 Baths
- Anna Maria SubDv.
- 34216 Zip Code
Under Construction. ~ Exquisite coastal luxury 5 bedrooms, 5 baths, and private pool home located on the North end of Anna Maria Island. This coastal home is ideally loca...
- 5 Beds
- 5.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Florida living at its finest! Located just steps away from the sandy Gulf Beaches of Anna Maria Island, this newly renovated 4 bedroom, 4 bathroom beach home awaits its n...
- 4 Beds
- 4 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
If you love to relax and watch the boats go by this home has the perfect view. During the day you can watch the kayakers, boaters and cruise ships passing in the bay. At ...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Stunning 7 Bedroom/4.5 bath home located in the heart of Anna Maria Island is being sold with a Bert Harris Award allowing 16 guests. Only 2 blocks from the beach, two st...
- 7 Beds
- 4.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Out of the box!! This brand new totally remodeled home in one of the most coveted locations on the north end of Anna Maria Island can be yours right out of the wrapper! ...
- 3 Beds
- 2 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Under Construction. Brand new bayfront luxury home with amazing water views and only 3 blocks to the beach. This fabulous eight-bedroom dream home offers high-end finishe...
- 8 Beds
- 8.5 Baths
- Azure Shores SubDv.
- 34217 Zip Code
Turtle Cove 4 bed / 2 bath home, presently set up as a duplex with (2) Bedroom, (1) Bath on each side. This updated oasis is a Short 100 step stroll to the Gulf of Mexico...
- 4 Beds
- 2 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. PRE-CONSTRUCTION: Get in on the ground floor of this New Home in Holmes Beach nestled in th...
- 4 Beds
- 5.5 Baths
- Sportsmans Harbor SubDv.
- 34217 Zip Code
Pre-Construction. To be built. Under Construction. Here's your opportunity to own a brand new beach house just steps away from the world famous beaches of Anna Maria Isla...
- 7 Beds
- 6.5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Evoking a Mediterranean-Spanish essence and island vibe, this charming residence allows you to immerse yourself in the Anna Maria Island lifestyle with ease and style. Ac...
- 3 Beds
- 3 Baths
- 4th Avenue Condominium SubDv.
- 34217 Zip Code
Looking for a vacation home "on the sand?" This is it! Mainsail's Beach Inn offers immediate access to the pristine beaches of Anna Maria Island on the Gulf of Mexico. En...
- 3 Beds
- 3 Baths
- Mainsail Beach Inn SubDv.
- 34217 Zip Code
Brand new Luxury Gulf Front Home positioned on the north end of Anna Maria Island, steps from Bean Point. This 4 bedroom, 4 full and 2 half bathroom home sits right on t...
- 4 Beds
- 4.5 Baths
- Wells Terrace SubDv.
- 34216 Zip Code
Pre-Construction. To be built. BRAND NEW CONSTRUCTION AT THE GULF OF MEXICO BY PREMIER, WELL RESPECTED BUILDER WHITEHEAD CONSTRUCTION. Soaring Gulf Views, Volume Ceilings...
- 4 Beds
- 4 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
THIS KEY WEST STYLE HOME IS BEING SOLD TURNKEY FURNISHED AND WAS BUILT WITH ALL HIGH END FINISHES INCLUDING SOLID GRANITE SURFACES, 8FT DOORS, TRAVERTINE AND WOOD GRAINED...
- 5 Beds
- 3.5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
CENTRALLY LOCATED IN Holmes Beach AND ONLY A SHORT STROLL TO THE BEACH, THIS HOME HAS IT ALL. IT WAS COMPLETELY RENOVATED A FEW YEARS AGO WITH VAULTED CEILINGS, WOOD GRA...
- 4 Beds
- 3 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
BEACH BLOCK HOME! Copy and paste this link into your web browser to view the virtual tour https://tours.coastalhomephotography.net/1848266?idx=1 Come and enjoy this 4 bed...
- 4 Beds
- 3.5 Baths
- Anna Maria Beach SubDv.
- 34216 Zip Code
Spectacular one of a kind duplex with some views of the fabulous beaches of Anna Maria and Sarasota Bay and only 95 steps to the beach. Each apartment offers over 1500 s...
- 4 Beds
- 5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Views, views, and more views! Bayfront Paradise has some of the most amazing views of Anna Maria Sound, Tampa Bay, and the Skyway Bridge. From the living room or bedroom,...
- 5 Beds
- 4.5 Baths
- Sportsmans Harbor SubDv.
- 34217 Zip Code
Welcome to "The Garden House" You will love this tropical hideaway right in the heart of Holmes Beach and walking distance to the beach! This adorable 3 bedroom home has ...
- 3 Beds
- 3 Baths
- Edgemere Sub SubDv.
- 34217 Zip Code
Under Construction. New luxury Key West style home with amazing views located between the bay and Gulf of Mexico. Gorgeous home that will feature professional décor, hig...
- 7 Beds
- 6.5 Baths
- Cortez Beach SubDv.
- 34217 Zip Code
ISLAND DREAMING....Beautifully appointed beach bungalow in the heart of Anna Maria. This recently renovated 4 bedroom, 3 bath home has an open floor plan featuring shipla...
- 4 Beds
- 3 Baths
- S C Cobbs Sub SubDv.
- 34217 Zip Code
Centrally located in Holmes Beach this 6BD/3.5BA Mediterranean style home is the perfect location for easy access to the beaches and shops and restaurants. Well appointe...
- 6 Beds
- 3.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
Investors dream of Vacation Rental Income as well as enjoying the property when it isn't rented. Highly sought after Gulf Place on Anna Maria Island in Holmes Beach is lo...
- 3 Beds
- 2 Baths
- Gulf Place SubDv.
- 34217 Zip Code
Pre-Construction. To be built. BRAND NEW CONSTRUCTION IN HOLMES BEACH NEXT TO SHOPS AND RESTAURANTS. THIS HOME WILL HAVE 4 BEDROOMS AND 4.5 BATHS AND AN OFFICE. FEATURES ...
- 4 Beds
- 4.5 Baths
- Holmes Beach SubDv.
- 34217 Zip Code
https://youtu.be/uB6tZyADFO4 ( copy and paste) Gorgeous Mediterranean style ,FULLY FURNISHED, Half Duplex, one block from Beautiful Bradenton Beach . This Luxury...
- 3 Beds
- 2 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
https://youtu.be/iNVfJ3t24Nw ( copy and paste ) Gorgeous Mediterranean style , Half Duplex, one block from Beautiful Bradenton Beach . This Luxury Condo features 3 b...
- 3 Beds
- 2 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
This Gulf Front estate is a beach lover’s dream! An incredibly-appointed, expansive home sitting right on 110’ of powdery white sand beaches of the exclusive, highly-sou...
- 5 Beds
- 5.5 Baths
- Banyan Bay SubDv.
- 34216 Zip Code
So close to the beach! Beautiful 4 BD 2BA island home with vaulted ceilings, luxurious furnishings and open floor plan for family, guests and entertaining in paradise. Ex...
- 4 Beds
- 2 Baths
- Holmes Gulf To Bay Dev Subdivison SubDv.
- 34217 Zip Code
Pre-Construction. To be built. TO BE BUILT. READY TO BREAK GROUND! INCREDIBLE INVESTMENT OPPORTUNITY! New luxury home with amazing views! This 7 bedroom dream home will ...
- 7 Beds
- 6.5 Baths
- Ilexhurst SubDv.
- 34217 Zip Code
Island Paradise on Homes Beach is a six unit complex directly on the Gulf of Mexico. The building is a contemporary design and the lush landscaping surrounds the large Gu...
- 3 Beds
- 2 Baths
- Island Paradise Condo SubDv.
- 34217 Zip Code
Mediterranean style 3 bedroom, 3 bathroom pool condominium located just blocks away a short stroll from the gorgeous beach of Anna Maria Island! These condominiums have e...
- 3 Beds
- 3 Baths
- Holmes Gulf To Bay Dev Subdivison SubDv.
- 34217 Zip Code
Whether making this your permanent home in "Paradise" or the ideal investment for vacation rental, this condominium complex does not disappoint. Excellent location on sm...
- 3 Beds
- 2 Baths
- Gulf Place SubDv.
- 34217 Zip Code
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
- 4.5 Baths
- Edgemere Sub SubDv.
- 34217 Zip Code