Real Estate Investment Properties for Sale in Big Pine Key, FL

Looking for investment property in Big Pine Key, FL with high ROI ?

Explore a variety of short-term homes & houses in Big Pine Key, FL. Invest wisely with VRBO & Big Pine Key, 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 Big Pine Key, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
29030 Iris Drive Big Pine Key, FL This 3BR spacious canal front home with quick open water access is nestled at the end of a...	3 beds \| 2 baths \| 1,353 sq.ft.	$669,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.7% Airbnb Rental Income: $1535 Traditional Rental Income: $3326 Airbnb ROI: 0.11% Traditional ROI: 3.7%
29850 Journeys End Road Big Pine Key, FL Nestled among lush tropical foliage, this inviting 3-bedroom, 2-bath home offers privacy, ...	3 beds \| 2 baths \| 1,152 sq.ft.	$785,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.8% Airbnb Rental Income: $1535 Traditional Rental Income: $2615 Airbnb ROI: -0.28% Traditional ROI: 1.8%
30170 Linda Street Big Pine Key, FL Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residenc...	1 beds \| 1 baths \| 528 sq.ft.	$415,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.1% Airbnb Rental Income: $1438 Traditional Rental Income: $1672 Airbnb ROI: 0.4% Traditional ROI: 2.1%
3746 Park Avenue Big Pine Key, FL Welcome to your private paradise in the Lower Keys! This beautifully updated 2 bed, 2 bath...	2 beds \| 2 baths \| 1,312 sq.ft.	$1,850,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.28% Airbnb Rental Income: $2198 Traditional Rental Income: $3006 Airbnb ROI: -0.52% Traditional ROI: 0.28%
1659 LONG BEACH DRIVE Big Pine Key, FL One of the only true luxury oceanfront estates with a private sandy beach available in the...	3 beds \| 2 baths \| 1,850 sq.ft.	$2,199,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.52% Airbnb Rental Income: $1535 Traditional Rental Income: $3852 Airbnb ROI: -0.84% Traditional ROI: 0.52%
29051 MAGNOLIA LANE Big Pine Key, FL Welcome to 29051 Magnolia Lane in Big Pine Key, FL! This inviting home offers a 2-bedroom,...	3 beds \| 3 baths \| 1,344 sq.ft.	$1,099,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.62% Airbnb Rental Income: $1535 Traditional Rental Income: $3346 Airbnb ROI: -0.59% Traditional ROI: 1.62%
31047 Avenue I Big Pine Key, FL Discover the charm of island living in this beautifully maintained 3-bedroom, 2.5-bath hom...	3 beds \| 3 baths \| 1,500 sq.ft.	$699,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.76% Airbnb Rental Income: $1535 Traditional Rental Income: $2904 Airbnb ROI: -0.02% Traditional ROI: 2.76%
31243 E Avenue Big Pine Key, FL *Price Enhancement Welcome to your slice of paradise in Big Pine Key! This charming 3-b...	3 beds \| 2 baths \| 1,204 sq.ft.	$634,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 2.28% Airbnb Rental Income: $1535 Traditional Rental Income: $2498 Airbnb ROI: -0.09% Traditional ROI: 2.28%
30461 Poinciana Rd Big Pine Key, FL Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 b...	3 beds \| 2 baths \| 1,431 sq.ft.	$544,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.6% Airbnb Rental Income: $1535 Traditional Rental Income: $3413 Airbnb ROI: 0.03% Traditional ROI: 4.6%
31568 AVENUE D Big Pine Key, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,536 sq.ft.	$727,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.09% Airbnb Rental Income: $1535 Traditional Rental Income: $3063 Airbnb ROI: 0.18% Traditional ROI: 3.09%
29523 Enterprise Avenue Big Pine Key, FL Welcome to effortless waterfront living in the heart of Big Pine Key. This updated canal-f...	3 beds \| 2 baths \| 1,539 sq.ft.	$1,080,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 3.29% Airbnb Rental Income: $1535 Traditional Rental Income: $5145 Airbnb ROI: -0.75% Traditional ROI: 3.29%
30363 Flamingo Lane Big Pine Key, FL Tranquility meets coastal living, discover this stunning concrete constructed home built i...	3 beds \| 3 baths \| 1,837 sq.ft.	$1,795,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.88% Airbnb Rental Income: $1535 Traditional Rental Income: $3928 Airbnb ROI: -0.82% Traditional ROI: 0.88%
1672 Pandorea Lane Big Pine Key, FL Lowest priced stilted canal-front home on Big Pine! 2/2 up. Recently updated. New central ...	3 beds \| 3 baths \| 912 sq.ft.	$799,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.81% Airbnb Rental Income: $1535 Traditional Rental Income: $2716 Airbnb ROI: -0.37% Traditional ROI: 1.81%
3962-3964 No Name Road Big Pine Key, FL Investment Opportunity! Waterfront duplex with 2BD\|1BA on each side. Property features con...	4 beds \| 2 baths \| 1,536 sq.ft.	$987,500	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.28% Airbnb Rental Income: $1535 Traditional Rental Income: $3583 Airbnb ROI: -0.43% Traditional ROI: 2.28%
30995 Watson Boulevard Big Pine Key, FL FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 ...	4 beds \| 3 baths \| 2,400 sq.ft.	$2,300,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 0.71% Airbnb Rental Income: $8598 Traditional Rental Income: $4183 Airbnb ROI: 2.02% Traditional ROI: 0.71%
1733 Sunrise Dr Big Pine Key, FL Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean an...	3 beds \| 2 baths \| 1,849 sq.ft.	$2,069,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.62% Airbnb Rental Income: $1535 Traditional Rental Income: $4128 Airbnb ROI: -0.97% Traditional ROI: 0.62%
1633 Lantana Lane Big Pine Key, FL Located in Big Pine Key, this 3-bedroom, 2-bathroom, canal front Pool Home is a perfect bl...	3 beds \| 2 baths \| 1,204 sq.ft.	$949,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.39% Airbnb Rental Income: $1535 Traditional Rental Income: $2829 Airbnb ROI: -0.58% Traditional ROI: 1.39%
550 Pine Lane Big Pine Key, FL This newly remodeled 2-bedroom, 1-bathroom home is perfectly positioned on two spacious lo...	3 beds \| 1 baths \| 1,043 sq.ft.	$1,275,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.61% Airbnb Rental Income: $1535 Traditional Rental Income: $2522 Airbnb ROI: -0.6% Traditional ROI: 0.61%
31490 Avenue F Big Pine Key, FL This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and f...	3 beds \| 3 baths \| 1,492 sq.ft.	$975,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.78% Airbnb Rental Income: $1535 Traditional Rental Income: $5960 Airbnb ROI: -0.59% Traditional ROI: 4.78%
30366 Falcon Lane Big Pine Key, FL Fantastic CBS canal front Pool home on a double lot in Tropical Bay Estates. Entering int...	3 beds \| 2 baths \| 1,398 sq.ft.	$1,249,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.74% Airbnb Rental Income: $1535 Traditional Rental Income: $5066 Airbnb ROI: -0.68% Traditional ROI: 2.74%
3 W Cook Big Pine Key, FL Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfron...	3 beds \| 2 baths \| 704 sq.ft.	$549,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.16% Airbnb Rental Income: $1535 Traditional Rental Income: $2277 Airbnb ROI: 0.85% Traditional ROI: 3.16%
1136 W SHORE Drive Big Pine Key, FL Don't miss out on this home... It is NOT a drive by.....Located on the West Side of the Is...	3 beds \| N/A baths \| 2,295 sq.ft.	$1,924,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.2% Airbnb Rental Income: $1535 Traditional Rental Income: $5044 Airbnb ROI: -1.01% Traditional ROI: 1.2%
3635 Tradewinds Street Big Pine Key, FL Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-ba...	2 beds \| 2 baths \| 1,042 sq.ft.	$840,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 1.45% Airbnb Rental Income: $2198 Traditional Rental Income: $2479 Airbnb ROI: 0.38% Traditional ROI: 1.45%
29559 Ranger Avenue Big Pine Key, FL This well desired location and immaculately maintained home is 5 minutes from world class ...	2 beds \| 3 baths \| 1,200 sq.ft.	$1,050,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.83% Airbnb Rental Income: $2198 Traditional Rental Income: $3146 Airbnb ROI: 0.29% Traditional ROI: 1.83%
1607 Sunrise Drive Big Pine Key, FL Open water pool home with breathtaking views of Bogie Channel and direct deep water access...	2 beds \| 2 baths \| 1,980 sq.ft.	$1,699,000	Airbnb cash on cash: -0.58% Traditional cash on cash: -0.12% Airbnb Rental Income: $2198 Traditional Rental Income: $2371 Airbnb ROI: -0.58% Traditional ROI: -0.12%
30246 Watson Boulevard Big Pine Key, FL Discover your dream home on Big Pine Key at this expansive 37,500 sq. ft., property totali...	3 beds \| 2 baths \| 1,193 sq.ft.	$799,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2% Airbnb Rental Income: $1535 Traditional Rental Income: $2588 Airbnb ROI: -0.01% Traditional ROI: 2%
29176 Violet Drive Big Pine Key, FL Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen p...	5 beds \| 4 baths \| 2,447 sq.ft.	$2,340,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.37% Airbnb Rental Income: $null Traditional Rental Income: $5940 Airbnb ROI: N/A Traditional ROI: 1.37%
30985 Hibiscus Drive Big Pine Key, FL CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning sta...	4 beds \| 3 baths \| 2,166 sq.ft.	$1,250,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 2.36% Airbnb Rental Income: $8598 Traditional Rental Income: $4771 Airbnb ROI: 4.25% Traditional ROI: 2.36%
29662 Independence Avenue Big Pine Key, FL Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home...	2 beds \| 2 baths \| 1,024 sq.ft.	$1,299,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 0.76% Airbnb Rental Income: $2198 Traditional Rental Income: $2580 Airbnb ROI: -0.02% Traditional ROI: 0.76%
29859 Overseas Highway #UNIT A-6 Big Pine Key, FL Own a Piece of Paradise - A Renovator's Dream!Embrace the possibilities with this project ...	2 beds \| 2 baths \| 780 sq.ft.	$234,900	Airbnb cash on cash: 5.1% Traditional cash on cash: 7.14% Airbnb Rental Income: $2198 Traditional Rental Income: $2096 Airbnb ROI: 5.1% Traditional ROI: 7.14%
32734 Bimini Lane Big Pine Key, FL Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a s...	3 beds \| 2 baths \| 1,654 sq.ft.	$1,149,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.47% Airbnb Rental Income: $1535 Traditional Rental Income: $3542 Airbnb ROI: -0.83% Traditional ROI: 1.47%
30416 Coconut Highway Big Pine Key, FL This 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV,...	2 beds \| 1 baths \| 1,497 sq.ft.	$718,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.18% Airbnb Rental Income: $2198 Traditional Rental Income: $2351 Airbnb ROI: 1.12% Traditional ROI: 2.18%
31450 Avenue G Big Pine Key, FL This expansive 4 bedroom, 3 bathroom home offers over 2,300 sq ft of solid concrete constr...	4 beds \| 3 baths \| 2,323 sq.ft.	$1,789,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.01% Airbnb Rental Income: $8598 Traditional Rental Income: $4139 Airbnb ROI: 2.72% Traditional ROI: 1.01%
31569 Avenue D Big Pine Key, FL Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete h...	4 beds \| 3 baths \| 1,896 sq.ft.	$1,189,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.13% Airbnb Rental Income: $8598 Traditional Rental Income: $3791 Airbnb ROI: 5.02% Traditional ROI: 2.13%
31441 Avenue F Big Pine Key, FL This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the p...	4 beds \| 3 baths \| 1,457 sq.ft.	$980,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 1.86% Airbnb Rental Income: $8598 Traditional Rental Income: $2968 Airbnb ROI: 6.26% Traditional ROI: 1.86%
31131 Ave D Big Pine Key, FL Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Be...	2 beds \| 1 baths \| 754 sq.ft.	$459,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.86% Airbnb Rental Income: $2198 Traditional Rental Income: $2081 Airbnb ROI: 1.84% Traditional ROI: 2.86%
3742 Seagrape Street Big Pine Key, FL Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front...	3 beds \| 3 baths \| 4,687 sq.ft.	$5,900,000	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.79% Airbnb Rental Income: $1535 Traditional Rental Income: $3839 Airbnb ROI: -1.29% Traditional ROI: -0.79%
31034 Hollerich Drive Big Pine Key, FL A great investment opportunity, or the chance for your paradise retreat to pay for itself!...	4 beds \| 2 baths \| 1,460 sq.ft.	$995,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 2.27% Airbnb Rental Income: $1389 Traditional Rental Income: $3489 Airbnb ROI: -0.45% Traditional ROI: 2.27%
29283 Coconut Palm Drive Big Pine Key, FL Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residentia...	3 beds \| 2 baths \| 1,247 sq.ft.	$715,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 2.81% Airbnb Rental Income: $1535 Traditional Rental Income: $2734 Airbnb ROI: 0.35% Traditional ROI: 2.81%
1433 Sunset Road Big Pine Key, FL Great income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogi...	4 beds \| 3 baths \| 1,924 sq.ft.	$839,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.8% Airbnb Rental Income: $1535 Traditional Rental Income: $4379 Airbnb ROI: -0.4% Traditional ROI: 3.8%

Real Estate investment in Big-pine-key, FL

There are 46 properties for sale in the city of Big Pine Key . The median list price in Big Pine Key is $995,000 and the average price per square foot is $635. In December 2025, the average monthly cash on cash return in Big Pine Key is 2.00%. The average monthly rental income in Big Pine Key is $2,743.

Big-pine-key, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 46 investment properties available for sale in Big-pine-key.

In 2025, the best neighborhood to buy investment property is Big Pine Key.

The ROI for Short-Term is higher than the Long-Term in Big-pine-key with average rental income of $1,535.

Your search for investment property begins and ends here

Investment Property for Sale in Big Pine Key, FL

29030 Iris Drive

Big Pine Key, FL

3 beds | 2 baths | 1,353 sq.ft.

$669,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1535

Traditional Rental Income: $3326

Airbnb ROI: 0.11%

Traditional ROI: 3.7%

29850 Journeys End Road

Big Pine Key, FL

3 beds | 2 baths | 1,152 sq.ft.

$785,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $1535

Traditional Rental Income: $2615

Airbnb ROI: -0.28%

Traditional ROI: 1.8%

30170 Linda Street

Big Pine Key, FL

1 beds | 1 baths | 528 sq.ft.

$415,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $1438

Traditional Rental Income: $1672

Airbnb ROI: 0.4%

Traditional ROI: 2.1%

3746 Park Avenue

Big Pine Key, FL

2 beds | 2 baths | 1,312 sq.ft.

$1,850,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $2198

Traditional Rental Income: $3006

Airbnb ROI: -0.52%

Traditional ROI: 0.28%

1659 LONG BEACH DRIVE

Big Pine Key, FL

3 beds | 2 baths | 1,850 sq.ft.

$2,199,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $1535

Traditional Rental Income: $3852

Airbnb ROI: -0.84%

Traditional ROI: 0.52%

29051 MAGNOLIA LANE

Big Pine Key, FL

3 beds | 3 baths | 1,344 sq.ft.

$1,099,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $1535

Traditional Rental Income: $3346

Airbnb ROI: -0.59%

Traditional ROI: 1.62%

31047 Avenue I

Big Pine Key, FL

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

$699,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $1535

Traditional Rental Income: $2904

Airbnb ROI: -0.02%

Traditional ROI: 2.76%

31243 E Avenue

Big Pine Key, FL

3 beds | 2 baths | 1,204 sq.ft.

$634,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1535

Traditional Rental Income: $2498

Airbnb ROI: -0.09%