Real Estate Investment Properties for Sale in Anna Maria, FL

Looking for investment property in Anna Maria, FL with high ROI ?

Explore a variety of short-term homes & houses in Anna Maria, FL. Invest wisely with VRBO & Anna Maria, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Anna Maria, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
313 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestle...	3 beds \| 2 baths \| 1,424 sq.ft.	$1,575,000	Airbnb cash on cash: -0.52% Traditional cash on cash: -0.1% Airbnb Rental Income: $3306 Traditional Rental Income: $3172 Airbnb ROI: -0.52% Traditional ROI: -0.1%
527 MAGNOLIA AVENUE ANNA MARIA, FL Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom,...	3 beds \| 2 baths \| 1,924 sq.ft.	$2,195,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.09% Airbnb Rental Income: $3306 Traditional Rental Income: $4093 Airbnb ROI: -0.84% Traditional ROI: -0.09%
704 GLADIOLUS STREET ANNA MARIA, FL PRICE CHANGE! You are just a short walk to Beach and Bay from this quality constructed 4 b...	4 beds \| 3 baths \| 2,415 sq.ft.	$2,945,000	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.6% Airbnb Rental Income: $3476 Traditional Rental Income: $4352 Airbnb ROI: -1.2% Traditional ROI: -0.6%
222 WILLOW AVENUE ANNA MARIA, FL Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable str...	4 beds \| 6 baths \| 3,265 sq.ft.	$4,800,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 0.53% Airbnb Rental Income: $3476 Traditional Rental Income: $11575 Airbnb ROI: -1.47% Traditional ROI: 0.53%
733 HOLLY ROAD ANNA MARIA, FL ***Welcome to Summer Breeze â a rare island gem on Anna Maria Islandâs coveted North E...	5 beds \| 4 baths \| 2,838 sq.ft.	$2,499,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.42% Airbnb Rental Income: $3130 Traditional Rental Income: $5694 Airbnb ROI: -0.99% Traditional ROI: 0.42%
212 OAK AVENUE ANNA MARIA, FL STUNNING RENOVATED 5 BEDROOM POOL HOME ON A DEEP WATER CANAL ONLY STEPS FROM THE BEACH!!! ...	5 beds \| 5 baths \| 3,844 sq.ft.	$3,950,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 0.48% Airbnb Rental Income: $3130 Traditional Rental Income: $8717 Airbnb ROI: -1.24% Traditional ROI: 0.48%
893 N SHORE DRIVE ANNA MARIA, FL One or more photo(s) has been virtually staged. One or more photos have been virtually sta...	4 beds \| 3 baths \| 2,933 sq.ft.	$3,499,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.56% Airbnb Rental Income: $3476 Traditional Rental Income: $6577 Airbnb ROI: -0.64% Traditional ROI: 0.56%
229 WILLOW AVENUE ANNA MARIA, FL Here is your chance to own a 5 bed/4.5 bath custom waterfront residence on one of the most...	5 beds \| 5 baths \| 3,250 sq.ft.	$6,375,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.81% Airbnb Rental Income: $3130 Traditional Rental Income: $7641 Airbnb ROI: -1.69% Traditional ROI: -0.81%
401 N SHORE DRIVE ANNA MARIA, FL Stunning Fully Remodeled 3-Bedroom Home with Pool & Spa â Prime North End Location. Welc...	3 beds \| 2 baths \| 1,680 sq.ft.	$2,200,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.37% Airbnb Rental Income: $3306 Traditional Rental Income: $3390 Airbnb ROI: -0.78% Traditional ROI: -0.37%
771 JACARANDA ROAD ANNA MARIA, FL An easy 5-minute walk to the Gulf on the coveted north end of Anna Maria Island, Limelight...	3 beds \| 2 baths \| 1,447 sq.ft.	$1,799,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -0.38% Airbnb Rental Income: $3306 Traditional Rental Income: $3213 Airbnb ROI: -0.77% Traditional ROI: -0.38%
111 CEDAR AVENUE ANNA MARIA, FL AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVA...	3 beds \| 3 baths \| 2,263 sq.ft.	$3,895,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.47% Airbnb Rental Income: $3306 Traditional Rental Income: $5227 Airbnb ROI: -1.21% Traditional ROI: -0.47%
103 SUNSET LANE ANNA MARIA, FL Tucked away at the end of a quiet cul-de-sac in Sunset Cove, this elevated beach home is a...	3 beds \| 3 baths \| 2,800 sq.ft.	$2,695,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.18% Airbnb Rental Income: $3306 Traditional Rental Income: $4152 Airbnb ROI: -0.45% Traditional ROI: 0.18%
519 VILLA ROSA WAY ANNA MARIA, FL This stunning property, situated on the premier private street of Anna Maria, was designed...	4 beds \| 5 baths \| 3,385 sq.ft.	$5,000,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.31% Airbnb Rental Income: $3476 Traditional Rental Income: $8447 Airbnb ROI: -0.93% Traditional ROI: 0.31%
912 N SHORE DRIVE ANNA MARIA, FL Gorgeous recently renovated 2-bedroom, 2-bathroom cottage is perfectly situated on the nor...	2 beds \| 2 baths \| 1,332 sq.ft.	$1,195,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.12% Airbnb Rental Income: $2055 Traditional Rental Income: $2597 Airbnb ROI: -0.85% Traditional ROI: 0.12%
510 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to Aloha Beaches. This home is a successful active rental in the city of Anna Mari...	4 beds \| 3 baths \| 2,225 sq.ft.	$2,995,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.42% Airbnb Rental Income: $3476 Traditional Rental Income: $4300 Airbnb ROI: -0.99% Traditional ROI: -0.42%
110 SPRING AVENUE ANNA MARIA, FL Welcome to this exceptional beach retreat, an exquisite 5-bedroom, 4.5-bath luxury coastal...	5 beds \| 5 baths \| 2,925 sq.ft.	$3,000,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.42% Airbnb Rental Income: $3130 Traditional Rental Income: $5041 Airbnb ROI: -1.37% Traditional ROI: -0.42%
136 CRESCENT DR ANNA MARIA, FL Best priced Anna Maria City move in ready single family home with room for a pool. Anna Ma...	2 beds \| 2 baths \| 1,068 sq.ft.	$1,199,999	Airbnb cash on cash: -1.09% Traditional cash on cash: -0.43% Airbnb Rental Income: $2055 Traditional Rental Income: $2256 Airbnb ROI: -1.09% Traditional ROI: -0.43%
115 LOS CEDROS DRIVE ANNA MARIA, FL Located on the highly sought-after North End of Anna Maria Island, 115 Los Cedrosâknown ...	4 beds \| 4 baths \| 2,203 sq.ft.	$2,290,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.63% Airbnb Rental Income: $3476 Traditional Rental Income: $5954 Airbnb ROI: -0.9% Traditional ROI: 0.63%
519 SOUTH DRIVE ANNA MARIA, FL âAnna Maria Oasisâ is a Bimini Bay Coastal Classic, perfectly positioned on the covete...	3 beds \| 2 baths \| 2,131 sq.ft.	$1,695,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.1% Airbnb Rental Income: $3306 Traditional Rental Income: $4305 Airbnb ROI: -1% Traditional ROI: 0.1%
115 N BAY BOULEVARD ANNA MARIA, FL Welcome to this stunning show stopping property on the North End of Anna Maria Island!Â Â ...	3 beds \| 4 baths \| 3,548 sq.ft.	$4,150,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.31% Airbnb Rental Income: $3306 Traditional Rental Income: $5271 Airbnb ROI: -1.02% Traditional ROI: -0.31%
116 HAMMOCK ROAD ANNA MARIA, FL Discover Mia Bella â a rare canal-front estate on Anna Maria Islandâs coveted North En...	4 beds \| 4 baths \| 2,366 sq.ft.	$2,395,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.43% Airbnb Rental Income: $3476 Traditional Rental Income: $4784 Airbnb ROI: -0.51% Traditional ROI: 0.43%
150 CRESCENT DRIVE ANNA MARIA, FL Ease into Island Life at Crescent Palms. If youâve been dreaming of that perfect, easy-...	3 beds \| 2 baths \| 1,765 sq.ft.	$1,790,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.49% Airbnb Rental Income: $3306 Traditional Rental Income: $3971 Airbnb ROI: -0.36% Traditional ROI: 0.49%
801 N SHORE DRIVE ANNA MARIA, FL Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless...	3 beds \| 4 baths \| 4,728 sq.ft.	$10,850,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -0.85% Airbnb Rental Income: $3306 Traditional Rental Income: $7514 Airbnb ROI: -1.34% Traditional ROI: -0.85%
57 N SHORE DRIVE ANNA MARIA, FL 57 North Shore Drive: The Art of Island Living Discover the perfect balance of classic An...	3 beds \| 3 baths \| 1,240 sq.ft.	$1,890,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.43% Airbnb Rental Income: $3306 Traditional Rental Income: $3076 Airbnb ROI: -0.72% Traditional ROI: -0.43%
50 N SHORE DRIVE ANNA MARIA, FL An exceptional opportunity to experience true island living where waterfront boating and b...	4 beds \| 5 baths \| 3,055 sq.ft.	$4,850,000	Airbnb cash on cash: -1.33% Traditional cash on cash: -0.08% Airbnb Rental Income: $3476 Traditional Rental Income: $8321 Airbnb ROI: -1.33% Traditional ROI: -0.08%
110 OAK AVENUE #A ANNA MARIA, FL Old Florida Charm â Income-Producing Property! Looking for a true Old Florida beach cott...	2 beds \| 2 baths \| 640 sq.ft.	$899,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.01% Airbnb Rental Income: $2055 Traditional Rental Income: $1965 Airbnb ROI: -0.54% Traditional ROI: -0.01%
870 N SHORE DRIVE ANNA MARIA, FL LOCATION!!!! North Shore Drive, one of the most popular streets in Anna Maria! This is a g...	4 beds \| 5 baths \| 2,091 sq.ft.	$3,895,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.69% Airbnb Rental Income: $3476 Traditional Rental Income: $4597 Airbnb ROI: -1.22% Traditional ROI: -0.69%
413 POINSETTIA ROAD ANNA MARIA, FL Back on the Market with a substantial price Adjustment!!!! Take another look at 413 Poinse...	2 beds \| 2 baths \| 1,677 sq.ft.	$1,595,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -0.12% Airbnb Rental Income: $2055 Traditional Rental Income: $3108 Airbnb ROI: -1.19% Traditional ROI: -0.12%
120 MAPLE AVENUE ANNA MARIA, FL Prime Beachside Retreat â Steps to the Sand on Anna Maria Island! Discover coastal livi...	3 beds \| 2 baths \| 1,506 sq.ft.	$1,575,000	Airbnb cash on cash: -0.38% Traditional cash on cash: -0.58% Airbnb Rental Income: $3306 Traditional Rental Income: $2274 Airbnb ROI: -0.38% Traditional ROI: -0.58%
821 S BAY BOULEVARD ANNA MARIA, FL A rare expression of modern island luxury, this newly constructed Polynesian-inspired esta...	5 beds \| 6 baths \| 4,964 sq.ft.	$7,995,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.83% Airbnb Rental Income: $3130 Traditional Rental Income: $2691 Airbnb ROI: -0.86% Traditional ROI: -0.83%
807 S BAY BOULEVARD ANNA MARIA, FL Experience the perfect blend of modern luxury and coastal functionality in this impeccably...	3 beds \| 2 baths \| 1,969 sq.ft.	$2,300,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -0.07% Airbnb Rental Income: $3306 Traditional Rental Income: $3125 Airbnb ROI: -0.34% Traditional ROI: -0.07%
866 N SHORE DRIVE ANNA MARIA, FL Don't miss your chance to own a fully remodeled home in the City of Anna Maria. Extensivel...	4 beds \| 4 baths \| 1,904 sq.ft.	$1,999,000	Airbnb cash on cash: -0.4% Traditional cash on cash: -0.19% Airbnb Rental Income: $3476 Traditional Rental Income: $3097 Airbnb ROI: -0.4% Traditional ROI: -0.19%
102 TUNA STREET ANNA MARIA, FL Finding a lot of this scale on one of Anna Mariaâs most quiet and secluded streets is an...	3 beds \| 3 baths \| 1,926 sq.ft.	$6,800,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -1.31% Airbnb Rental Income: $3306 Traditional Rental Income: $3491 Airbnb ROI: -1.46% Traditional ROI: -1.31%
313 HAMMOCK CIRCLE ANNA MARIA, FL This waterfront coastal retreat embodies refined island luxury, offered completely turnkey...	4 beds \| 4 baths \| 3,755 sq.ft.	$4,495,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -1.11% Airbnb Rental Income: $3476 Traditional Rental Income: $3607 Airbnb ROI: -1.32% Traditional ROI: -1.11%
108 PELICAN DRIVE ANNA MARIA, FL Located on the north end of Anna Maria, this elevated canal-front home is a true boaterâ...	4 beds \| 2 baths \| 1,472 sq.ft.	$2,295,000	Airbnb cash on cash: -0.21% Traditional cash on cash: -0.17% Airbnb Rental Income: $3476 Traditional Rental Income: $2796 Airbnb ROI: -0.21% Traditional ROI: -0.17%
111 PALMETTO AVENUE ANNA MARIA, FL Experience elevated island living in this exceptional brand-new custom four bedroom four a...	4 beds \| 5 baths \| 2,677 sq.ft.	$5,250,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -0.6% Airbnb Rental Income: $3476 Traditional Rental Income: $3505 Airbnb ROI: -0.77% Traditional ROI: -0.6%
403 N BAY BOULEVARD ANNA MARIA, FL AVAILABLE TO SHOW THIS SATURDAY, 3/7/26 FROM NOON - 2PM. PLEASE CALL REALTOR TO SCHEDULE. ...	4 beds \| 3 baths \| 2,112 sq.ft.	$2,650,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -1.03% Airbnb Rental Income: $3476 Traditional Rental Income: $2767 Airbnb ROI: -1.06% Traditional ROI: -1.03%
519 LOQUAT DRIVE ANNA MARIA, FL Welcome to 519 Loquat Drive, an exceptional waterfront retreat in the heart of Anna Maria....	4 beds \| 4 baths \| 2,606 sq.ft.	$2,995,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.73% Airbnb Rental Income: $3476 Traditional Rental Income: $3545 Airbnb ROI: -1.03% Traditional ROI: -0.73%
108 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to your dream coastal retreat at 108 Magnolia Ave on the north end of Anna Maria! ...	4 beds \| 4 baths \| 3,052 sq.ft.	$4,199,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.95% Airbnb Rental Income: $3476 Traditional Rental Income: $4719 Airbnb ROI: -1.47% Traditional ROI: -0.95%
903 N SHORE DRIVE #B ANNA MARIA, FL Welcome to this stunning show stopping property on the North End of Anna Maria Island very...	4 beds \| 5 baths \| 2,915 sq.ft.	$5,595,000	Airbnb cash on cash: -1.48% Traditional cash on cash: -1.32% Airbnb Rental Income: $3476 Traditional Rental Income: $3505 Airbnb ROI: -1.48% Traditional ROI: -1.32%

Real Estate investment in Anna-maria, FL

There are 62 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,745,000 and the average price per square foot is $1,159. In April 2026, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,864.

Anna-maria, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 62 investment properties available for sale in Anna-maria.

In 2026, the best neighborhood to buy investment property is ANNA MARIA.

The ROI for Short-Term is higher than the Long-Term in Anna-maria with average rental income of $3,306.

Your search for investment property begins and ends here

Investment Property for Sale in Anna Maria, FL

313 MAGNOLIA AVENUE

ANNA MARIA, FL

3 beds | 2 baths | 1,424 sq.ft.

$1,575,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: -0.1%

Airbnb Rental Income: $3306

Traditional Rental Income: $3172

Airbnb ROI: -0.52%

Traditional ROI: -0.1%

527 MAGNOLIA AVENUE

ANNA MARIA, FL

3 beds | 2 baths | 1,924 sq.ft.

$2,195,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: -0.09%

Airbnb Rental Income: $3306

Traditional Rental Income: $4093

Airbnb ROI: -0.84%

Traditional ROI: -0.09%

704 GLADIOLUS STREET

ANNA MARIA, FL

4 beds | 3 baths | 2,415 sq.ft.

$2,945,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: -0.6%

Airbnb Rental Income: $3476

Traditional Rental Income: $4352

Airbnb ROI: -1.2%

Traditional ROI: -0.6%

222 WILLOW AVENUE

ANNA MARIA, FL

4 beds | 6 baths | 3,265 sq.ft.

$4,800,000

Airbnb cash on cash: -1.47%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $3476

Traditional Rental Income: $11575

Airbnb ROI: -1.47%

Traditional ROI: 0.53%

733 HOLLY ROAD

ANNA MARIA, FL

5 beds | 4 baths | 2,838 sq.ft.

$2,499,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $3130

Traditional Rental Income: $5694

Airbnb ROI: -0.99%

Traditional ROI: 0.42%

212 OAK AVENUE

ANNA MARIA, FL

5 beds | 5 baths | 3,844 sq.ft.

$3,950,000

Airbnb cash on cash: -1.24%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $3130

Traditional Rental Income: $8717

Airbnb ROI: -1.24%

Traditional ROI: 0.48%

893 N SHORE DRIVE

ANNA MARIA, FL

4 beds | 3 baths | 2,933 sq.ft.

$3,499,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 0.56%

Airbnb Rental Income: $3476

Traditional Rental Income: $6577

Airbnb ROI: -0.64%

Traditional ROI: 0.56%

229 WILLOW AVENUE

ANNA MARIA, FL

5 beds | 5 baths | 3,250 sq.ft.

$6,375,000

Airbnb cash on cash: -1.69%

Traditional cash on cash: -0.81%

Airbnb Rental Income: $3130

Traditional Rental Income: $7641

Airbnb ROI: -1.69%