Florida Gulf Coast Vacation Homes for Sale
The Central Florida Gulf Coast is a popular destination for vacationers from all over the world. With its beautiful beaches, world-class theme parks, and mild weather, the area is a year-round playground. This demand for vacation rentals has created a strong market for Central Florida Gulf Coast vacation homes.
If you’re considering investing in a vacation home in this area, there are a few things you should keep in mind. First, the demand for vacation rentals is high, so you’re likely to be able to rent your home out for most of the year. Second, the prices of vacation homes in this area are relatively affordable, so you can get a good return on your investment.
Contact us today to learn more about how Holiday Realty LLC can help you with your Central Florida Gulf Coast vacation home investment.
Search all short term rental properties for sale on the Central Florida Gulf Coast
704 Gladiolus St, Anna Maria, Florida 34216
Residential For Sale
ISLAND REAL ESTATE-ANNA MARIA
You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool home with private elevator.
$2,995,000
607 S Bay Boulevard, Anna Maria, Florida 34216
Residential For Sale
SATO REAL ESTATE INC.
This 4 bedroom, 3 bathroom waterfront home on a canal with spectacular outdoor space with multiple decks and both bay and canal views! The home is situated at the north end of the island within an easy bike or golf cart ride to Anna Maria's Pine Avenue shops, the bayside beach, Anna Maria City Pier and gulf-side beaches! The home's ground floor has a one car garage an indoor/outdoor space with si
$2,895,000
796 Jacaranda Rd, Anna Maria, Florida 34216
Residential For Sale
ANNA MARIA ISLAND BEACHES RE
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, SOLID WOOD CABINETS, HARDWOOD FLOORS, VOLUME CEILINGS, NEW S/S APPLIANCES, ELEVATOR, AND COMES TURNKEY FURNISHED WITH A COASTAL DECOR. OUTSIDE IT HAS A METAL ROOF, IMPACT WINDOWS AND DOORS, HARDI SIDING, AND TROPICAL LANDSCAPING.
$2,875,000
103 Sunset Ln, Anna Maria, Florida 34216
Residential For Sale
DUNCAN REAL ESTATE, INC.
Tucked away at the end of a quiet cul-de-sac in Sunset Cove, this elevated beach home is all about location— just steps from the sugar-sand shoreline of Anna Maria with beach access just around the corner. Designed by architect H.
$2,695,000
509 Pine Ave #a, Anna Maria, Florida 34216
Residential For Sale
RE/MAX ALLIANCE GROUP
Income-Producing Property or Commercial Opportunity – Prime Pine Avenue Location!
Attention investors and business-minded buyers! 509 Pine Avenue offers a rare chance to own a dual-zoned (residential/commercial) property in the heart of Anna Maria Island — ideal for those seeking immediate rental income, a business location, or the flexibility to do both.
$2,500,000
733 Holly Rd, Anna Maria, Florida 34216
Residential For Sale
RE/MAX ALLIANCE GROUP
Welcome to Summer Breeze - A rare island gem tucked away on Anna Maria’s coveted North End! This elevated 5-bedroom, 4-bath coastal retreat sits on an oversized corner ¼-acre lot surrounded by lush tropical landscaping, just steps from the world-famous Bean Point beach. Whether you're seeking the ultimate family getaway or a high-performing investment property, Summer Breeze delivers.
$2,500,000
526 Loquat Dr, Anna Maria, Florida 34216
Residential For Sale
AN ISLAND PLACE REALTY INC
You have to see this home to appreciate the efficient layout and spacious living spaces. This property comes turnkey furnished, making it a seamless transition for the fortunate new owners. Meticulously maintained and never rented, the home exudes a sense of care and pride. For those considering short-term rentals, this residence presents an attractive opportunity.
$2,450,000
616 Fern St, Anna Maria, Florida 34216
Residential For Sale
SATO REAL ESTATE INC.
Under contract-accepting backup offers. THIS is PARADISE! Enjoy this like-new construction beautiful 3 bedroom, 3 bathroom multi-leveled home. Nestled on the north end of Anna Maria Island just steps away from the sparkling waters of the Gulf and Bay as well as close to Pine Ave! Enjoy the natural sunlight open concept and the professionally decorated interior design.
$2,425,000
311 Iris St, Anna Maria, Florida 34216
Residential For Sale
DUNCAN REAL ESTATE, INC.
Under contract-accepting backup offers. Surrounded by lush tropical beauty on the north end of Anna Maria Island, this lovingly maintained canal front home invites you to embrace island living with both style and ease.
$2,350,000
401 N Shore Dr, Anna Maria, Florida 34216
Residential For Sale
NDC REALTY, LLC
Stunning Fully Remodeled 3-Bedroom Home with Pool & Spa – Prime North End Location. Welcome to your dream coastal retreat! This beautifully remodeled 3-bedroom, 2-bath home was completely transformed in the spring of 2025 and professionally decorated with designer furnishings. Since the renovation, the home has never been occupied—offering a truly brand-new interior experience.
$2,200,000
527 Magnolia Ave, Anna Maria, Florida 34216
Residential For Sale
DUNCAN REAL ESTATE, INC.
Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom, 2-bathroom waterfront retreat offers the perfect blend of coastal elegance and island convenience. Being sold turnkey with a strong rental history and bookings in place, this property is an ideal investment opportunity or full-time residence.
$2,195,000
307 Spring Ave, Anna Maria, Florida 34216
Residential For Sale
ANNA MARIA LIFE REAL ESTATE
~~~~~ READY.....SET..... HERE'S YOUR DEAL! ~~~~~ Come take a look at this amazing Anna Maria home. Villa Maria is ready for you! An amazing 3 bedroom, 2 bathroom and a half bath just 2.5 blocks away from some of the most coveted beaches in the country. This popular vacation rental is perfectly nestled in the city of Anna Maria.
$2,125,000
785 Jacaranda Rd, Anna Maria, Florida 34216
Residential For Sale
ISLAND REAL ESTATE-ANNA MARIA
OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to enjoy about this great investment home! This is the perfect beach haven, just a hop, skip & a jump to the Gulf beach! Just steps to Bean Point, this elevated 3 bed/2.5 bath pool home is a great income property! Updated with beautiful coastal style, this home is designed for relaxing.
$1,999,900
312 Hardin Ave, Anna Maria, Florida 34216
Residential For Sale
ANNA MARIA LIFE REAL ESTATE
WELCOME to Bimini Bay – Your Oasis Awaits! Step into your dream getaway at Bimini Bay, where this stunning home offers everything you need for the perfect beach house in paradise. Ideal for both vacationers and renters alike, this four-bedroom, three-bathroom retreat is nestled in the charming heart of Anna Maria.
$1,999,500
110 Palmetto Ave, Anna Maria, Florida 34216
Residential For Sale
ISLAND REAL ESTATE-ANNA MARIA
Under contract-accepting backup offers. Prime location at Anna Maria's north end. West of Gulf Drive and only 3 houses to the Gulf. Home was hurricane damaged and being sold for lot value.
$1,850,000
511 Spring Ave, Anna Maria, Florida 34216
Residential For Sale
BLUESRQ REAL ESTATE INC
Welcome to Cabana Breeze, an elevated, eco-friendly retreat on the coveted north end of Anna Maria Island. Complete with solar panels—this four-bedroom, two-bath home sits just a short walk from Anna Maria City Beach and steps from Pine Avenue’s popular shops and restaurants.
$1,825,000
