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
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.	$4,899,000	Airbnb cash on cash: 0.61% Traditional cash on cash: -0.01% Airbnb Rental Income: $10781 Traditional Rental Income: $5997 Airbnb ROI: 0.61% Traditional ROI: -0.01%
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.	$3,950,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.11% Airbnb Rental Income: $9368 Traditional Rental Income: $7412 Airbnb ROI: -0.05% Traditional ROI: -0.11%
136 CRESCENT DR ANNA MARIA, FL Anna Maria Island charming remodeled coastal cottage offered for sale for the first time i...	2 beds \| 2 baths \| 1,068 sq.ft.	$1,249,000	Airbnb cash on cash: 0.89% Traditional cash on cash: -0.53% Airbnb Rental Income: $4769 Traditional Rental Income: $2141 Airbnb ROI: 0.89% Traditional ROI: -0.53%
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.	$5,975,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.1% Airbnb Rental Income: $10781 Traditional Rental Income: $7593 Airbnb ROI: 0.32% Traditional ROI: 0.1%
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.	$3,800,000	Airbnb cash on cash: 0.32% Traditional cash on cash: -0.92% Airbnb Rental Income: $10781 Traditional Rental Income: $4428 Airbnb ROI: 0.32% Traditional ROI: -0.92%
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: 1.17% Traditional cash on cash: -0.17% Airbnb Rental Income: $10781 Traditional Rental Income: $5065 Airbnb ROI: 1.17% Traditional ROI: -0.17%
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: 1.27% Traditional cash on cash: -0.66% Airbnb Rental Income: $6697 Traditional Rental Income: $2383 Airbnb ROI: 1.27% Traditional ROI: -0.66%
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.	$2,290,000	Airbnb cash on cash: 0.49% Traditional cash on cash: -0.47% Airbnb Rental Income: $6697 Traditional Rental Income: $3362 Airbnb ROI: 0.49% Traditional ROI: -0.47%
807 S BAY BOULEVARD ANNA MARIA, FL Elevated Island Dream on Anna Maria! Embrace the quintessential Anna Maria Island lifestyl...	3 beds \| 2 baths \| 1,969 sq.ft.	$2,300,000	Airbnb cash on cash: 1.01% Traditional cash on cash: -0.05% Airbnb Rental Income: $6697 Traditional Rental Income: $3125 Airbnb ROI: 1.01% Traditional ROI: -0.05%
216 ARCHER WAY ANNA MARIA, FL Opportunity knocks at Anna Maria Island's much desired North End. This 3 bedroom/2 bath ho...	3 beds \| 2 baths \| 1,020 sq.ft.	$895,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 1.55% Airbnb Rental Income: $6697 Traditional Rental Income: $2640 Airbnb ROI: 4.85% Traditional ROI: 1.55%
612 FERN STREET ANNA MARIA, FL Welcome to Anna Maria Chateau, a beautiful vacation rental nestled on a peaceful street at...	3 beds \| 2 baths \| 1,472 sq.ft.	$1,950,000	Airbnb cash on cash: 0.54% Traditional cash on cash: -0.96% Airbnb Rental Income: $6697 Traditional Rental Income: $2671 Airbnb ROI: 0.54% Traditional ROI: -0.96%
216 PALMETTO AVENUE ANNA MARIA, FL Welcome to your dream coastal retreat! This fully furnished, elevated 2 bedroom, 1 bathro...	2 beds \| 1 baths \| 1,008 sq.ft.	$1,675,000	Airbnb cash on cash: 0.16% Traditional cash on cash: -1.04% Airbnb Rental Income: $4769 Traditional Rental Income: $1906 Airbnb ROI: 0.16% Traditional ROI: -1.04%
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.	$4,150,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.6% Airbnb Rental Income: $9368 Traditional Rental Income: $5965 Airbnb ROI: -0.17% 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.	$4,995,000	Airbnb cash on cash: -0.13% Traditional cash on cash: -0.06% Airbnb Rental Income: $10781 Traditional Rental Income: $9145 Airbnb ROI: -0.13% Traditional ROI: -0.06%
704 GLADIOLUS STREET ANNA MARIA, FL Embrace Island Life in this perfectly situated North End 4 bed/3 bath pool home with only ...	4 beds \| 3 baths \| 2,415 sq.ft.	$2,995,000	Airbnb cash on cash: 0.99% Traditional cash on cash: -0.87% Airbnb Rental Income: $10781 Traditional Rental Income: $3609 Airbnb ROI: 0.99% Traditional ROI: -0.87%
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.	$3,795,000	Airbnb cash on cash: -0.14% Traditional cash on cash: -1.05% Airbnb Rental Income: $9368 Traditional Rental Income: $4407 Airbnb ROI: -0.14% Traditional ROI: -1.05%
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.	$2,900,000	Airbnb cash on cash: 0.94% Traditional cash on cash: -0.4% Airbnb Rental Income: $9368 Traditional Rental Income: $3997 Airbnb ROI: 0.94% Traditional ROI: -0.4%
315 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to your slice of paradise! Nestled in the heart of Anna Maria Island, this adorabl...	2 beds \| 2 baths \| 999 sq.ft.	$1,495,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 0.09% Airbnb Rental Income: $4769 Traditional Rental Income: $2056 Airbnb ROI: 1.34% Traditional ROI: 0.09%
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.	$2,440,000	Airbnb cash on cash: 0.43% Traditional cash on cash: -0.28% Airbnb Rental Income: $6697 Traditional Rental Income: $3776 Airbnb ROI: 0.43% Traditional ROI: -0.28%
401 N BAY BOULEVARD ANNA MARIA, FL Perfectly positioned just steps from the sparkling turquoise waters of Tampa Bay, this ele...	2 beds \| 3 baths \| 1,710 sq.ft.	$1,995,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.14% Airbnb Rental Income: $4769 Traditional Rental Income: $2749 Airbnb ROI: 0.7% Traditional ROI: 0.14%
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: -0.3% Traditional cash on cash: -1.34% Airbnb Rental Income: $4769 Traditional Rental Income: $1523 Airbnb ROI: -0.3% 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.	$4,995,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -0.43% Airbnb Rental Income: $10781 Traditional Rental Income: $6935 Airbnb ROI: -0.02% Traditional ROI: -0.43%
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.	$575,000	Airbnb cash on cash: 3.06% Traditional cash on cash: -0.66% Airbnb Rental Income: $4769 Traditional Rental Income: $1788 Airbnb ROI: 3.06% Traditional ROI: -0.66%
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: -0.81% Traditional cash on cash: -0.85% Airbnb Rental Income: $9368 Traditional Rental Income: $7388 Airbnb ROI: -0.81% 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: 0.18% Traditional cash on cash: -0.3% Airbnb Rental Income: $9368 Traditional Rental Income: $5840 Airbnb ROI: 0.18% Traditional ROI: -0.3%
413 POINSETTIA ROAD ANNA MARIA, FL What would you think if you could find a completely renovated two-bedroom two-bath open fl...	2 beds \| 2 baths \| 1,677 sq.ft.	$2,050,000	Airbnb cash on cash: 0.04% Traditional cash on cash: -0.39% Airbnb Rental Income: $4769 Traditional Rental Income: $2973 Airbnb ROI: 0.04% Traditional ROI: -0.39%
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: 0.97% Traditional cash on cash: -0.01% Airbnb Rental Income: $10781 Traditional Rental Income: $5167 Airbnb ROI: 0.97% Traditional ROI: -0.01%
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: 0.61% Traditional cash on cash: -0.64% Airbnb Rental Income: $6697 Traditional Rental Income: $2846 Airbnb ROI: 0.61% 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: 3.97% Traditional cash on cash: 0.58% Airbnb Rental Income: $10781 Traditional Rental Income: $3777 Airbnb ROI: 3.97% Traditional ROI: 0.58%
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: 0.83% Traditional cash on cash: -1.09% Airbnb Rental Income: $6697 Traditional Rental Income: $2024 Airbnb ROI: 0.83% 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: $10781 Traditional Rental Income: $10270 Airbnb ROI: 0.7% Traditional ROI: 1.06%
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: 0.35% Traditional cash on cash: -0.11% Airbnb Rental Income: $9368 Traditional Rental Income: $5495 Airbnb ROI: 0.35% Traditional ROI: -0.11%
212 MAGNOLIA AVENUE ANNA MARIA, FL Beach Walks, Pool Days, and Endless Island Living Await. Just a 4-minute stroll to the san...	3 beds \| 2 baths \| 1,292 sq.ft.	$1,450,000	Airbnb cash on cash: 1.63% Traditional cash on cash: -0.65% Airbnb Rental Income: $6697 Traditional Rental Income: $2310 Airbnb ROI: 1.63% Traditional ROI: -0.65%
785 JACARANDA ROAD ANNA MARIA, FL Under contract-accepting backup offers. NEW PRICE! Steps to the beach at Bean Point this e...	3 beds \| 3 baths \| 1,500 sq.ft.	$1,999,900	Airbnb cash on cash: 0.67% Traditional cash on cash: -0.71% Airbnb Rental Income: $6697 Traditional Rental Income: $2832 Airbnb ROI: 0.67% Traditional ROI: -0.71%
110 HAMMOCK ROAD ANNA MARIA, FL Under contract-accepting backup offers. Welcome to island living! Nestled on the north end...	4 beds \| 2 baths \| 2,654 sq.ft.	$1,695,000	Airbnb cash on cash: 3.26% Traditional cash on cash: -0.34% Airbnb Rental Income: $10781 Traditional Rental Income: $3115 Airbnb ROI: 3.26% Traditional ROI: -0.34%
511 LOQUAT DRIVE ANNA MARIA, FL Under contract-accepting backup offers. BRING THE BOAT! BRING THE FAMILY! Fun and relaxat...	4 beds \| 5 baths \| 2,752 sq.ft.	$3,300,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 0.27% Airbnb Rental Income: $10781 Traditional Rental Income: $7360 Airbnb ROI: 0.74% Traditional ROI: 0.27%
103 PARK AVENUE ANNA MARIA, FL Under contract-accepting backup offers. EXCEPTIONAL COASTAL LIVING AT IT'S FINEST!!! ONE H...	5 beds \| 5 baths \| 4,540 sq.ft.	$5,995,000	Airbnb cash on cash: -1.14% Traditional cash on cash: -1.21% Airbnb Rental Income: $9368 Traditional Rental Income: $7205 Airbnb ROI: -1.14% Traditional ROI: -1.21%
799 JACARANDA ROAD ANNA MARIA, FL Under contract-accepting backup offers. Located on the sought-after north end of Anna Mari...	2 beds \| 2 baths \| 1,100 sq.ft.	$1,475,000	Airbnb cash on cash: 0.36% Traditional cash on cash: -0.82% Airbnb Rental Income: $4769 Traditional Rental Income: $2170 Airbnb ROI: 0.36% Traditional ROI: -0.82%
108 PELICAN DRIVE ANNA MARIA, FL Located on the coveted north end of Anna Maria Island, this elevated canal-front retreat o...	4 beds \| 2 baths \| 1,472 sq.ft.	$1,450,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 0.31% Airbnb Rental Income: $10781 Traditional Rental Income: $2796 Airbnb ROI: 4.77% Traditional ROI: 0.31%
764 N SHORE DRIVE ANNA MARIA, FL Under contract-accepting backup offers. GULF VIEWS & ISLAND VIBES: A COASTAL RETREAT LIKE ...	3 beds \| 2 baths \| 1,768 sq.ft.	$1,300,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.66% Airbnb Rental Income: $6697 Traditional Rental Income: $2695 Airbnb ROI: 2.89% Traditional ROI: 0.66%

Real Estate investment in Anna-maria, FL

There are 40 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,325,000 and the average price per square foot is $1,032. In September 2025, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,785.

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

There are 40 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 $6,697.

Your search for investment property begins and ends here

Investment Property for Sale in Anna Maria, FL

111 GULL DRIVE

ANNA MARIA, FL

4 beds | 5 baths | 2,905 sq.ft.

$4,899,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $10781

Traditional Rental Income: $5997

Airbnb ROI: 0.61%

Traditional ROI: -0.01%

108 TERN DRIVE

ANNA MARIA, FL

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

$3,950,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $9368

Traditional Rental Income: $7412

Airbnb ROI: -0.05%

Traditional ROI: -0.11%

136 CRESCENT DR

ANNA MARIA, FL

2 beds | 2 baths | 1,068 sq.ft.

$1,249,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: -0.53%

Airbnb Rental Income: $4769

Traditional Rental Income: $2141

Airbnb ROI: 0.89%

Traditional ROI: -0.53%

329 TARPON STREET

ANNA MARIA, FL

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

$5,975,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $10781

Traditional Rental Income: $7593

Airbnb ROI: 0.32%

Traditional ROI: 0.1%

870 N SHORE DRIVE

ANNA MARIA, FL

4 beds | 5 baths | 2,091 sq.ft.

$3,800,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: -0.92%

Airbnb Rental Income: $10781

Traditional Rental Income: $4428

Airbnb ROI: 0.32%

Traditional ROI: -0.92%

418 MAGNOLIA AVENUE

ANNA MARIA, FL

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

$2,995,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $10781

Traditional Rental Income: $5065

Airbnb ROI: 1.17%

Traditional ROI: -0.17%

313 MAGNOLIA AVENUE

ANNA MARIA, FL

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

$1,675,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $6697

Traditional Rental Income: $2383

Airbnb ROI: 1.27%

Traditional ROI: -0.66%

527 MAGNOLIA AVENUE

ANNA MARIA, FL

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

$2,290,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: -0.47%

Airbnb Rental Income: $6697

Traditional Rental Income: $3362

Airbnb ROI: 0.49%