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
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: -0.45% Airbnb Rental Income: $3306 Traditional Rental Income: $3362 Airbnb ROI: -0.84% Traditional ROI: -0.45%
329 TARPON STREET ANNA MARIA, FL Experience the charm of Anna Maria Island with this NEWLY COMPLETED CONSTRUCTION. This lux...	4 beds \| 5 baths \| 3,751 sq.ft.	$5,750,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.14% Airbnb Rental Income: $3476 Traditional Rental Income: $7593 Airbnb ROI: -0.77% Traditional ROI: 0.14%
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.	$1,675,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.66% Airbnb Rental Income: $3306 Traditional Rental Income: $2383 Airbnb ROI: -0.55% Traditional ROI: -0.66%
785 JACARANDA ROAD ANNA MARIA, FL OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to ...	3 beds \| 3 baths \| 1,500 sq.ft.	$1,999,900	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.71% Airbnb Rental Income: $3306 Traditional Rental Income: $2832 Airbnb ROI: -0.85% Traditional ROI: -0.71%
113 MAPLE AVENUE ANNA MARIA, FL THIS INCREDIBLE CUSTOM BUILT ESTATE IS JUST FIVE HOUSES FROM THE GULF AND NESTLED ON ONE O...	5 beds \| 5 baths \| 2,680 sq.ft.	$3,690,000	Airbnb cash on cash: -1.59% Traditional cash on cash: -0.56% Airbnb Rental Income: $3130 Traditional Rental Income: $5965 Airbnb ROI: -1.59% Traditional ROI: -0.56%
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.	$4,995,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.06% Airbnb Rental Income: $3476 Traditional Rental Income: $9145 Airbnb ROI: -1.45% Traditional ROI: -0.06%
120 WHITE AVENUE ANNA MARIA, FL Nestled on Anna Maria Islandâs most famous street, this beautifully renovated coastal re...	5 beds \| 4 baths \| 2,763 sq.ft.	$3,497,500	Airbnb cash on cash: -1.67% Traditional cash on cash: -1.06% Airbnb Rental Income: $3130 Traditional Rental Income: $4407 Airbnb ROI: -1.67% Traditional ROI: -1.06%
704 GLADIOLUS STREET ANNA MARIA, FL You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool...	4 beds \| 3 baths \| 2,415 sq.ft.	$2,995,000	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.87% Airbnb Rental Income: $3476 Traditional Rental Income: $3609 Airbnb ROI: -1.2% Traditional ROI: -0.87%
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.	$2,500,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.31% Airbnb Rental Income: $3130 Traditional Rental Income: $3997 Airbnb ROI: -0.99% Traditional ROI: -0.31%
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: -0.3% Airbnb Rental Income: $3130 Traditional Rental Income: $5840 Airbnb ROI: -1.24% Traditional ROI: -0.3%
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: -0.85% Airbnb Rental Income: $3130 Traditional Rental Income: $7388 Airbnb ROI: -1.69% Traditional ROI: -0.85%
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: -0.64% Airbnb Rental Income: $3306 Traditional Rental Income: $2846 Airbnb ROI: -0.78% Traditional ROI: -0.64%
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: -1.1% Airbnb Rental Income: $3306 Traditional Rental Income: $2024 Airbnb ROI: -0.77% Traditional ROI: -1.1%
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.	$3,990,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.01% Airbnb Rental Income: $3476 Traditional Rental Income: $5167 Airbnb ROI: -0.68% Traditional ROI: -0.01%
112 MAPLE AVENUE ANNA MARIA, FL STUNNING NEW CONSTRUCTION HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED...	5 beds \| 5 baths \| 2,545 sq.ft.	$4,965,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.11% Airbnb Rental Income: $3130 Traditional Rental Income: $5495 Airbnb ROI: -0.78% Traditional ROI: -0.11%
513 BAYVIEW PLACE ANNA MARIA, FL This Bayview Palace is a One of a kind, thereâs nothing quite like this on Anna Maria Is...	4 beds \| 6 baths \| 3,464 sq.ft.	$3,999,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.31% Airbnb Rental Income: $3476 Traditional Rental Income: $10270 Airbnb ROI: -0.73% Traditional ROI: 1.31%
412 ALAMANDA ROAD ANNA MARIA, FL This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, fl...	2 beds \| 2 baths \| 1,168 sq.ft.	$1,650,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.44% Airbnb Rental Income: $2055 Traditional Rental Income: $2344 Airbnb ROI: -0.97% Traditional ROI: -0.44%
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: -1.11% Airbnb Rental Income: $3306 Traditional Rental Income: $2935 Airbnb ROI: -1.21% Traditional ROI: -1.11%
113 PALMETTO AVENUE ANNA MARIA, FL Under Construction. Welcome to 113 Palmetto Avenue, an architectural showcase by Eason Bui...	4 beds \| 5 baths \| 2,220 sq.ft.	$5,500,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.27% Airbnb Rental Income: $3476 Traditional Rental Income: $5335 Airbnb ROI: -0.78% Traditional ROI: -0.27%
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: 0.12% Airbnb Rental Income: $3306 Traditional Rental Income: $3991 Airbnb ROI: -0.45% Traditional ROI: 0.12%
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: 0.12% Airbnb Rental Income: $3476 Traditional Rental Income: $7544 Airbnb ROI: -0.93% Traditional ROI: 0.12%
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.	$1,244,000	Airbnb cash on cash: -1.09% Traditional cash on cash: -0.55% Airbnb Rental Income: $2055 Traditional Rental Income: $2141 Airbnb ROI: -1.09% Traditional ROI: -0.55%
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: 0.12% Airbnb Rental Income: $3476 Traditional Rental Income: $5806 Airbnb ROI: -0.99% Traditional ROI: 0.12%
527 BAYVIEW PLACE ANNA MARIA, FL Discover the potential of this two-bedroom, two-bathroom home situated on a generous 6,500...	2 beds \| 2 baths \| 1,246 sq.ft.	$1,100,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.77% Airbnb Rental Income: $2055 Traditional Rental Income: $2253 Airbnb ROI: 0.06% Traditional ROI: 0.77%
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: -0.18% Airbnb Rental Income: $3130 Traditional Rental Income: $5723 Airbnb ROI: -1.37% Traditional ROI: -0.18%
159 CRESCENT DRIVE ANNA MARIA, FL Location, location, Location. Welcome to Tropical Paradise. What more can you ask for in t...	4 beds \| 3 baths \| 2,567 sq.ft.	$2,995,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.65% Airbnb Rental Income: $3476 Traditional Rental Income: $3646 Airbnb ROI: -0.99% Traditional ROI: -0.65%
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: -0.03% Airbnb Rental Income: $2055 Traditional Rental Income: $2430 Airbnb ROI: -0.85% Traditional ROI: -0.03%
301 PALM AVENUE ANNA MARIA, FL One or more photo(s) has been virtually staged. Come feast your eyes on 301 Palm Avenue. F...	2 beds \| 2 baths \| 1,120 sq.ft.	$1,095,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.27% Airbnb Rental Income: $3306 Traditional Rental Income: $2287 Airbnb ROI: 0.54% Traditional ROI: 0.27%
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.	$1,995,000	Airbnb cash on cash: -0.46% Traditional cash on cash: -0.42% Airbnb Rental Income: $3306 Traditional Rental Income: $2642 Airbnb ROI: -0.46% Traditional ROI: -0.42%
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.	$1,750,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.65% Airbnb Rental Income: $3306 Traditional Rental Income: $3141 Airbnb ROI: -1% Traditional ROI: -0.65%
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 \| 2,013 sq.ft.	$2,495,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.39% Airbnb Rental Income: $3476 Traditional Rental Income: $4821 Airbnb ROI: -0.53% Traditional ROI: 0.39%
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.	$2,495,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.18% Airbnb Rental Income: $3476 Traditional Rental Income: $4387 Airbnb ROI: -0.91% Traditional ROI: -0.18%
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.	$4,395,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.61% Airbnb Rental Income: $3306 Traditional Rental Income: $4217 Airbnb ROI: -1.02% Traditional ROI: -0.61%
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.	$2,095,900	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.7% Airbnb Rental Income: $3306 Traditional Rental Income: $2653 Airbnb ROI: -0.75% Traditional ROI: -0.7%
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.	$1,995,000	Airbnb cash on cash: -0.42% Traditional cash on cash: -0.05% Airbnb Rental Income: $3306 Traditional Rental Income: $3249 Airbnb ROI: -0.42% Traditional ROI: -0.05%
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.	$10,950,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -1.19% Airbnb Rental Income: $3306 Traditional Rental Income: $4094 Airbnb ROI: -1.34% Traditional ROI: -1.19%
413 POINSETTIA ROAD ANNA MARIA, FL Back on the Market!!!! Take another look at 413 Poinsettia Rd. Once you walk through the d...	2 beds \| 2 baths \| 1,677 sq.ft.	$1,950,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.35% Airbnb Rental Income: $2055 Traditional Rental Income: $2973 Airbnb ROI: -1.15% Traditional ROI: -0.35%
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: -0.39% Airbnb Rental Income: $3476 Traditional Rental Income: $6935 Airbnb ROI: -1.33% Traditional ROI: -0.39%
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: -0.18% Airbnb Rental Income: $2055 Traditional Rental Income: $1826 Airbnb ROI: -0.54% Traditional ROI: -0.18%
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: -0.74% Airbnb Rental Income: $3476 Traditional Rental Income: $4428 Airbnb ROI: -1.22% Traditional ROI: -0.74%

Real Estate investment in Anna-maria, FL

There are 51 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,500,000 and the average price per square foot is $1,092. In February 2026, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,829.

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

There are 51 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

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: -0.45%

Airbnb Rental Income: $3306

Traditional Rental Income: $3362

Airbnb ROI: -0.84%

Traditional ROI: -0.45%

329 TARPON STREET

ANNA MARIA, FL

4 beds | 5 baths | 3,751 sq.ft.

$5,750,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $3476

Traditional Rental Income: $7593

Airbnb ROI: -0.77%

Traditional ROI: 0.14%

313 MAGNOLIA AVENUE

ANNA MARIA, FL

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

$1,675,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $3306

Traditional Rental Income: $2383

Airbnb ROI: -0.55%

Traditional ROI: -0.66%

785 JACARANDA ROAD

ANNA MARIA, FL

3 beds | 3 baths | 1,500 sq.ft.

$1,999,900

Airbnb cash on cash: -0.85%

Traditional cash on cash: -0.71%

Airbnb Rental Income: $3306

Traditional Rental Income: $2832

Airbnb ROI: -0.85%

Traditional ROI: -0.71%

113 MAPLE AVENUE

ANNA MARIA, FL

5 beds | 5 baths | 2,680 sq.ft.

$3,690,000

Airbnb cash on cash: -1.59%

Traditional cash on cash: -0.56%

Airbnb Rental Income: $3130

Traditional Rental Income: $5965

Airbnb ROI: -1.59%

Traditional ROI: -0.56%

222 WILLOW AVENUE

ANNA MARIA, FL

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

$4,995,000

Airbnb cash on cash: -1.45%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $3476

Traditional Rental Income: $9145

Airbnb ROI: -1.45%

Traditional ROI: -0.06%

120 WHITE AVENUE

ANNA MARIA, FL

5 beds | 4 baths | 2,763 sq.ft.

$3,497,500

Airbnb cash on cash: -1.67%

Traditional cash on cash: -1.06%

Airbnb Rental Income: $3130

Traditional Rental Income: $4407

Airbnb ROI: -1.67%

Traditional ROI: -1.06%

704 GLADIOLUS STREET

ANNA MARIA, FL

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

$2,995,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $3476

Traditional Rental Income: $3609

Airbnb ROI: -1.2%