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.

Single Family Homes for Sale in Anna Maria, FL

Search for Single Family Residential for Sale in Anna Maria, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 61 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
215 SYCAMORE AVENUE ANNA MARIA, FL Welcome to a rare offering on the coveted north end of Anna Maria Island â a brand-new c...	4 beds \| 5 baths \| 3,250 sq.ft.	$5,895,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0% Airbnb Rental Income: $9956 Traditional Rental Income: $6840 Airbnb ROI: 0.23% Traditional ROI: 0%

Your search for investment property begins and ends here

Single Family Homes 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%