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
108 TERN DRIVE ANNA MARIA, FL Welcome to your island oasis! This stunning modern waterfront home redefines relaxation. S...	5 beds \| 6 baths \| 3,874 sq.ft.	$3,550,000	Airbnb cash on cash: -1.55% Traditional cash on cash: -0.01% Airbnb Rental Income: $3050 Traditional Rental Income: $7412 Airbnb ROI: -1.55% Traditional ROI: -0.01%
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.	$5,850,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.12% Airbnb Rental Income: $3747 Traditional Rental Income: $7593 Airbnb ROI: -0.74% Traditional ROI: 0.12%
418 MAGNOLIA AVENUE ANNA MARIA, FL Sea Vous Play is 4 bedroom, 4.5 bathroom home located on Anna Maria Island. The home has a...	4 beds \| 5 baths \| 2,186 sq.ft.	$2,995,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.17% Airbnb Rental Income: $3747 Traditional Rental Income: $5065 Airbnb ROI: -0.94% Traditional ROI: -0.17%
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%
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.	$3,890,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.58% Airbnb Rental Income: $3050 Traditional Rental Income: $5965 Airbnb ROI: -1.58% Traditional ROI: -0.58%
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: -1.4% Traditional cash on cash: -0.06% Airbnb Rental Income: $3747 Traditional Rental Income: $9145 Airbnb ROI: -1.4% 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: -1.69% Traditional cash on cash: -1.06% Airbnb Rental Income: $3050 Traditional Rental Income: $4407 Airbnb ROI: -1.69% 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: -1.12% Traditional cash on cash: -0.87% Airbnb Rental Income: $3747 Traditional Rental Income: $3609 Airbnb ROI: -1.12% Traditional ROI: -0.87%
616 FERN STREET ANNA MARIA, FL THIS is PARADISE! Enjoy this like-new construction beautiful 3 bedroom, 3 bathroom multi-...	3 beds \| 3 baths \| 2,156 sq.ft.	$2,425,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.28% Airbnb Rental Income: $3306 Traditional Rental Income: $3776 Airbnb ROI: -0.81% Traditional ROI: -0.28%
733 HOLLY ROAD ANNA MARIA, FL Welcome to Summer Breeze - A rare island gem tucked away on Anna Mariaâs coveted North E...	5 beds \| 4 baths \| 2,838 sq.ft.	$2,500,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.31% Airbnb Rental Income: $3050 Traditional Rental Income: $3997 Airbnb ROI: -1.02% Traditional ROI: -0.31%
411 ALAMANDA ROAD ANNA MARIA, FL Incredible opportunity on the North end of Anna Maria Island. Located in the heart of the...	N/A beds \| N/A baths \| 2,880 sq.ft.	$2,350,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -1.34% Airbnb Rental Income: $3306 Traditional Rental Income: $1523 Airbnb ROI: -0.86% Traditional ROI: -1.34%
50 N SHORE DRIVE ANNA MARIA, FL Welcome to your dream coastal retreat on beautiful Anna Maria Island! This stunning 4-bedr...	4 beds \| 5 baths \| 3,055 sq.ft.	$4,895,000	Airbnb cash on cash: -1.3% Traditional cash on cash: -0.41% Airbnb Rental Income: $3747 Traditional Rental Income: $6935 Airbnb ROI: -1.3% Traditional ROI: -0.41%
522 PINE AVENUE #6B ANNA MARIA, FL This is your chance to fall in love with this hidden gem - 2 bedroom, 1 bathroom WATERFRON...	2 beds \| 1 baths \| 822 sq.ft.	$549,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -0.64% Airbnb Rental Income: $2123 Traditional Rental Income: $1788 Airbnb ROI: -1.05% Traditional ROI: -0.64%
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: -1.7% Traditional cash on cash: -0.85% Airbnb Rental Income: $3050 Traditional Rental Income: $7388 Airbnb ROI: -1.7% Traditional ROI: -0.85%
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: -1.25% Traditional cash on cash: -0.3% Airbnb Rental Income: $3050 Traditional Rental Income: $5840 Airbnb ROI: -1.25% Traditional ROI: -0.3%
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%
709 GLADIOLUS STREET ANNA MARIA, FL Great opportunity for investors and homeowners to start over and design to your very own t...	4 beds \| 3 baths \| 1,933 sq.ft.	$1,595,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.58% Airbnb Rental Income: $3747 Traditional Rental Income: $3777 Airbnb ROI: 0.01% Traditional ROI: 0.58%
893 N SHORE DRIVE ANNA MARIA, FL One or more photo(s) has been virtually staged. Waterfront Living on Anna Maria Island â...	4 beds \| 3 baths \| 2,933 sq.ft.	$3,990,000	Airbnb cash on cash: -0.62% Traditional cash on cash: -0.01% Airbnb Rental Income: $3747 Traditional Rental Income: $5167 Airbnb ROI: -0.62% Traditional ROI: -0.01%
771 JACARANDA ROAD ANNA MARIA, FL Welcome to Limelight â a beautifully appointed and fully furnished 3-bedroom, 2-bath coa...	3 beds \| 2 baths \| 1,447 sq.ft.	$1,890,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -1.09% Airbnb Rental Income: $3306 Traditional Rental Income: $2024 Airbnb ROI: -0.78% Traditional ROI: -1.09%
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.	$4,495,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.06% Airbnb Rental Income: $3747 Traditional Rental Income: $10270 Airbnb ROI: -0.7% Traditional ROI: 1.06%
403 N SHORE DRIVE ANNA MARIA, FL Discover unparalleled elegance in this stunning 3,400 sq. ft. very private residence 5 hou...	5 beds \| 7 baths \| 3,400 sq.ft.	$5,995,000	Airbnb cash on cash: -1.53% Traditional cash on cash: -0.33% Airbnb Rental Income: $3050 Traditional Rental Income: $9066 Airbnb ROI: -1.53% Traditional ROI: -0.33%
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: -0.79% Traditional cash on cash: -0.11% Airbnb Rental Income: $3050 Traditional Rental Income: $5495 Airbnb ROI: -0.79% Traditional ROI: -0.11%
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: -0.94% Traditional cash on cash: -0.44% Airbnb Rental Income: $2123 Traditional Rental Income: $2344 Airbnb ROI: -0.94% Traditional ROI: -0.44%
111 GULL DRIVE ANNA MARIA, FL Significant price drop makes this an incredible opportunity!!!! Stunning, brand new constr...	4 beds \| 5 baths \| 2,905 sq.ft.	$4,499,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.09% Airbnb Rental Income: $3747 Traditional Rental Income: $5997 Airbnb ROI: -0.64% Traditional ROI: 0.09%
311 IRIS STREET ANNA MARIA, FL Surrounded by lush tropical beauty on the north end of Anna Maria Island, this lovingly ma...	3 beds \| 2 baths \| 2,233 sq.ft.	$2,350,000	Airbnb cash on cash: -0.59% Traditional cash on cash: -0.03% Airbnb Rental Income: $3306 Traditional Rental Income: $3794 Airbnb ROI: -0.59% Traditional ROI: -0.03%
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%
216 ARCHER WAY ANNA MARIA, FL Under contract-accepting backup offers. Opportunity knocks at Anna Maria Island's much des...	3 beds \| 2 baths \| 1,020 sq.ft.	$895,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.55% Airbnb Rental Income: $3306 Traditional Rental Income: $2640 Airbnb ROI: 1.46% Traditional ROI: 1.55%
407 PINE AVENUE ANNA MARIA, FL Under contract-accepting backup offers. The Captivating Luxury Listing! Experience the...	4 beds \| 5 baths \| 3,022 sq.ft.	$3,999,000	Airbnb cash on cash: -1.41% Traditional cash on cash: -0.4% Airbnb Rental Income: $3747 Traditional Rental Income: $6650 Airbnb ROI: -1.41% Traditional ROI: -0.4%
110 PALMETTO AVENUE ANNA MARIA, FL Under contract-accepting backup offers. Prime location at Anna Maria's north end. West of...	1 beds \| 1 baths \| 596 sq.ft.	$1,850,000	Airbnb cash on cash: -0.29% Traditional cash on cash: -0.43% Airbnb Rental Income: $2337 Traditional Rental Income: $1527 Airbnb ROI: -0.29% Traditional ROI: -0.43%
239 GLADIOLUS STREET ANNA MARIA, FL Under contract-accepting backup offers. Welcome to your island retreat on beautiful Anna M...	3 beds \| 2 baths \| 1,296 sq.ft.	$1,450,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.88% Airbnb Rental Income: $3306 Traditional Rental Income: $2305 Airbnb ROI: -0.69% Traditional ROI: -0.88%

Real Estate investment in Anna-maria, FL

There are 32 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,995,000 and the average price per square foot is $1,252. In November 2025, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,818.

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

There are 32 investment properties available for sale in Anna-maria.

In 2025, 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

108 TERN DRIVE

ANNA MARIA, FL

5 beds | 6 baths | 3,874 sq.ft.

$3,550,000

Airbnb cash on cash: -1.55%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $3050

Traditional Rental Income: $7412

Airbnb ROI: -1.55%

Traditional ROI: -0.01%

329 TARPON STREET

ANNA MARIA, FL

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

$5,850,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $3747

Traditional Rental Income: $7593

Airbnb ROI: -0.74%

Traditional ROI: 0.12%

418 MAGNOLIA AVENUE

ANNA MARIA, FL

4 beds | 5 baths | 2,186 sq.ft.

$2,995,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $3747

Traditional Rental Income: $5065

Airbnb ROI: -0.94%

Traditional ROI: -0.17%

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%

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.

$3,890,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: -0.58%

Airbnb Rental Income: $3050

Traditional Rental Income: $5965

Airbnb ROI: -1.58%

Traditional ROI: -0.58%

222 WILLOW AVENUE

ANNA MARIA, FL

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

$4,995,000

Airbnb cash on cash: -1.4%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $3747

Traditional Rental Income: $9145

Airbnb ROI: -1.4%