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: 1.53% Traditional cash on cash: 0.02% Airbnb Rental Income: $6906 Traditional Rental Income: $3358 Airbnb ROI: 1.53% Traditional ROI: 0.02%
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: -0.25% Traditional cash on cash: 0.6% Airbnb Rental Income: $9956 Traditional Rental Income: $11922 Airbnb ROI: -0.25% Traditional ROI: 0.6%
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: 0.77% Traditional cash on cash: -0.52% Airbnb Rental Income: $9956 Traditional Rental Income: $4584 Airbnb ROI: 0.77% Traditional ROI: -0.52%
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: N/A Traditional cash on cash: 0.72% Airbnb Rental Income: $null Traditional Rental Income: $6373 Airbnb ROI: N/A Traditional ROI: 0.72%
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: N/A Traditional cash on cash: -0.55% Airbnb Rental Income: $null Traditional Rental Income: $9134 Airbnb ROI: N/A Traditional ROI: -0.55%
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: N/A Traditional cash on cash: 0.7% Airbnb Rental Income: $null Traditional Rental Income: $9512 Airbnb ROI: N/A Traditional ROI: 0.7%
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: 0.69% Traditional cash on cash: -0.19% Airbnb Rental Income: $6906 Traditional Rental Income: $3761 Airbnb ROI: 0.69% Traditional ROI: -0.19%
893 N SHORE DRIVE ANNA MARIA, FL One or more photo(s) has been virtually staged. Price reduced â dramatic value on Anna M...	4 beds \| 3 baths \| 2,933 sq.ft.	$2,950,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 1.16% Airbnb Rental Income: $9956 Traditional Rental Income: $7443 Airbnb ROI: 1.41% Traditional ROI: 1.16%
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: -0.38% Traditional cash on cash: -0.39% Airbnb Rental Income: $6906 Traditional Rental Income: $5519 Airbnb ROI: -0.38% Traditional ROI: -0.39%
103 SUNSET LANE ANNA MARIA, FL A premier setting defines this offering. Tucked at the end of a quiet cul-de-sac in Sunset...	3 beds \| 3 baths \| 2,800 sq.ft.	$2,395,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.48% Airbnb Rental Income: $6906 Traditional Rental Income: $4491 Airbnb ROI: 0.96% Traditional ROI: 0.48%
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: 0.24% Traditional cash on cash: 0.52% Airbnb Rental Income: $9956 Traditional Rental Income: $9413 Airbnb ROI: 0.24% Traditional ROI: 0.52%
136 CRESCENT DR ANNA MARIA, FL The Beach Is Calling!!! Best priced Anna Maria City move in ready single family home with ...	2 beds \| 2 baths \| 1,068 sq.ft.	$1,149,999	Airbnb cash on cash: 1.28% Traditional cash on cash: -0.15% Airbnb Rental Income: $5105 Traditional Rental Income: $2530 Airbnb ROI: 1.28% Traditional ROI: -0.15%
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: 0.95% Traditional cash on cash: -0.4% Airbnb Rental Income: $9956 Traditional Rental Income: $4357 Airbnb ROI: 0.95% Traditional ROI: -0.4%
110 SPRING AVENUE ANNA MARIA, FL Welcome to one of Anna Maria Island's most distinctive addresses â a 5-bedroom, 4.5-bath...	5 beds \| 5 baths \| 2,925 sq.ft.	$3,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.15% Airbnb Rental Income: $null Traditional Rental Income: $5813 Airbnb ROI: N/A Traditional ROI: -0.15%
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: 1.44% Traditional cash on cash: 0.29% Airbnb Rental Income: $5105 Traditional Rental Income: $2786 Airbnb ROI: 1.44% Traditional ROI: 0.29%
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.	$1,598,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 0.54% Airbnb Rental Income: $6906 Traditional Rental Income: $4852 Airbnb ROI: 1.02% Traditional ROI: 0.54%
154 CRESCENT DRIVE ANNA MARIA, FL Location! Location! Location! TRY BEFORE YOU BUY!!** Come Visitâ¦Fall in Love with luxur...	3 beds \| 3 baths \| 1,421 sq.ft.	$1,799,900	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.34% Airbnb Rental Income: $6906 Traditional Rental Income: $3805 Airbnb ROI: 1.39% Traditional ROI: 0.34%
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: 1.64% Traditional cash on cash: 0.89% Airbnb Rental Income: $9956 Traditional Rental Income: $6507 Airbnb ROI: 1.64% Traditional ROI: 0.89%
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: -0.24% Traditional cash on cash: -0.07% Airbnb Rental Income: $6906 Traditional Rental Income: $6218 Airbnb ROI: -0.24% Traditional ROI: -0.07%
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: 1.45% Traditional cash on cash: 0.56% Airbnb Rental Income: $6906 Traditional Rental Income: $4093 Airbnb ROI: 1.45% Traditional ROI: 0.56%
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.	$9,850,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -0.69% Airbnb Rental Income: $6906 Traditional Rental Income: $8842 Airbnb ROI: -1.05% Traditional ROI: -0.69%
413 POINSETTIA ROAD ANNA MARIA, FL Back on the Market! Take a look at 413 Poinsettia Rd. Once you walk through the door you w...	2 beds \| 2 baths \| 1,800 sq.ft.	$1,595,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 0.14% Airbnb Rental Income: $5105 Traditional Rental Income: $3491 Airbnb ROI: 0.53% Traditional ROI: 0.14%
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.	$4,650,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.27% Airbnb Rental Income: $9956 Traditional Rental Income: $9668 Airbnb ROI: -0.09% Traditional ROI: 0.27%
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: 0.28% Traditional cash on cash: -0.45% Airbnb Rental Income: $9956 Traditional Rental Income: $5463 Airbnb ROI: 0.28% Traditional ROI: -0.45%
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.	$849,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 0.13% Airbnb Rental Income: $5105 Traditional Rental Income: $2033 Airbnb ROI: 2.7% Traditional ROI: 0.13%
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.	$1,545,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 0.04% Airbnb Rental Income: $6906 Traditional Rental Income: $3157 Airbnb ROI: 1.72% Traditional ROI: 0.04%
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.	$2,199,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 0.37% Airbnb Rental Income: $9956 Traditional Rental Income: $3825 Airbnb ROI: 2.47% Traditional ROI: 0.37%
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: -0.98% Traditional cash on cash: -1.11% Airbnb Rental Income: $6906 Traditional Rental Income: $4783 Airbnb ROI: -0.98% Traditional ROI: -1.11%
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.	$3,995,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.14% Airbnb Rental Income: $9956 Traditional Rental Income: $8262 Airbnb ROI: 0.1% Traditional ROI: 0.14%
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.	$5,125,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.2% Airbnb Rental Income: $9956 Traditional Rental Income: $7302 Airbnb ROI: 0.37% Traditional ROI: 0.2%
403 N BAY BOULEVARD ANNA MARIA, FL AVAIABLE TO BE SHOWN SUNDAY 5/17/26 FROM 10AM - 3PM - LARGE PRICE REDUCTION â Now Priced...	4 beds \| 3 baths \| 2,112 sq.ft.	$2,473,000	Airbnb cash on cash: 1.29% Traditional cash on cash: -0.34% Airbnb Rental Income: $9956 Traditional Rental Income: $4367 Airbnb ROI: 1.29% Traditional ROI: -0.34%
103 PALM AVENUE ANNA MARIA, FL Welcome to 103 Palm Avenue on Anna Maria Island, home to some of the best beaches in Flori...	4 beds \| 4 baths \| 2,252 sq.ft.	$6,050,000	Airbnb cash on cash: -0.15% Traditional cash on cash: -0.74% Airbnb Rental Income: $9956 Traditional Rental Income: $4803 Airbnb ROI: -0.15% Traditional ROI: -0.74%
155 CRESCENT DRIVE ANNA MARIA, FL Your private island retreat awaits in this exquisitely renovated coastal cottage, situated...	3 beds \| 2 baths \| 1,512 sq.ft.	$1,900,000	Airbnb cash on cash: 0.8% Traditional cash on cash: -0.17% Airbnb Rental Income: $6906 Traditional Rental Income: $3858 Airbnb ROI: 0.8% Traditional ROI: -0.17%
112 CEDAR AVENUE ANNA MARIA, FL Completely remodeled 4-bedroom, 4-bathroom coastal retreat blending the charm of an origin...	4 beds \| 4 baths \| 1,800 sq.ft.	$2,795,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.38% Airbnb Rental Income: $9956 Traditional Rental Income: $5098 Airbnb ROI: 1.54% Traditional ROI: 0.38%
811 N SHORE DRIVE ANNA MARIA, FL Experience one of the most extraordinary waterfront settings on the coveted North End of A...	4 beds \| 8 baths \| 5,079 sq.ft.	$10,950,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 0.22% Airbnb Rental Income: $9956 Traditional Rental Income: $16033 Airbnb ROI: -0.56% Traditional ROI: 0.22%
109 TERN DRIVE ANNA MARIA, FL Delightful waterfront home on the famed North end of Anna Maria Island. This 2 bedroom 2 ...	2 beds \| 2 baths \| 1,223 sq.ft.	$1,499,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.1% Airbnb Rental Income: $5105 Traditional Rental Income: $3262 Airbnb ROI: 0.68% Traditional ROI: 0.1%
246 GLADIOLUS STREET ANNA MARIA, FL Kick off your shoes and come enjoy this Island home with a truly Anna Maria feel. This is ...	3 beds \| 3 baths \| 1,979 sq.ft.	$1,999,000	Airbnb cash on cash: 0.36% Traditional cash on cash: -0.25% Airbnb Rental Income: $6906 Traditional Rental Income: $4435 Airbnb ROI: 0.36% Traditional ROI: -0.25%
406 N SHORE DRIVE ANNA MARIA, FL Under Construction. Luxury residence coming soon in the heart of Anna Maria! This 4 bedroo...	4 beds \| 5 baths \| 2,999 sq.ft.	$5,450,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.53% Airbnb Rental Income: $9956 Traditional Rental Income: $8513 Airbnb ROI: 0.45% Traditional ROI: 0.53%
165 CRESCENT DRIVE ANNA MARIA, FL Charming coastal retreat located at 165 Crescent Dr in the heart of Anna Maria! This beaut...	3 beds \| 2 baths \| 1,403 sq.ft.	$1,695,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 0.2% Airbnb Rental Income: $6906 Traditional Rental Income: $3857 Airbnb ROI: 1.28% Traditional ROI: 0.2%
889 N SHORE DRIVE ANNA MARIA, FL This Bayfront home is calling your name! Perfectly positioned directly on the bay, this 3-...	3 beds \| 3 baths \| 2,025 sq.ft.	$4,500,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.91% Airbnb Rental Income: $6906 Traditional Rental Income: $4095 Airbnb ROI: -0.55% Traditional ROI: -0.91%

Real Estate investment in Anna-maria, FL

There are 63 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,795,000 and the average price per square foot is $1,189. In May 2026, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,934.

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

There are 63 investment properties available for sale in Anna-maria.

The ROI for Short-Term is higher than the Long-Term in Anna-maria with average rental income of $6,906.

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: 1.53%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $6906

Traditional Rental Income: $3358

Airbnb ROI: 1.53%

Traditional ROI: 0.02%

222 WILLOW AVENUE

ANNA MARIA, FL

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

$4,800,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $9956

Traditional Rental Income: $11922

Airbnb ROI: -0.25%

Traditional ROI: 0.6%

704 GLADIOLUS STREET

ANNA MARIA, FL

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

$2,945,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: -0.52%

Airbnb Rental Income: $9956

Traditional Rental Income: $4584

Airbnb ROI: 0.77%

Traditional ROI: -0.52%

733 HOLLY ROAD

ANNA MARIA, FL

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

$2,499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.72%

Airbnb Rental Income: $null

Traditional Rental Income: $6373

Airbnb ROI: N/A

Traditional ROI: 0.72%

229 WILLOW AVENUE

ANNA MARIA, FL

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

$6,375,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.55%

Airbnb Rental Income: $null

Traditional Rental Income: $9134

Airbnb ROI: N/A

Traditional ROI: -0.55%

212 OAK AVENUE

ANNA MARIA, FL

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

$3,950,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.7%

Airbnb Rental Income: $null

Traditional Rental Income: $9512

Airbnb ROI: N/A

Traditional ROI: 0.7%

401 N SHORE DRIVE

ANNA MARIA, FL

3 beds | 2 baths | 1,680 sq.ft.

$2,200,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $6906

Traditional Rental Income: $3761

Airbnb ROI: 0.69%

Traditional ROI: -0.19%

893 N SHORE DRIVE

ANNA MARIA, FL

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

$2,950,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $9956

Traditional Rental Income: $7443

Airbnb ROI: 1.41%