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
29034 Rose Drive Big Pine Key, FL Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key cana...	2 beds \| 1 baths \| 864 sq.ft.	$795,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 4.29% Airbnb Rental Income: $2687 Traditional Rental Income: $4559 Airbnb ROI: 0.9% Traditional ROI: 4.29%
3746 Park Avenue Big Pine Key, FL Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-...	2 beds \| 2 baths \| 1,312 sq.ft.	$1,399,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.67% Airbnb Rental Income: $2687 Traditional Rental Income: $4285 Airbnb ROI: -0.05% Traditional ROI: 1.67%
29175 Violet Drive Big Pine Key, FL Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted R...	3 beds \| 2 baths \| 986 sq.ft.	$685,000	Airbnb cash on cash: 9.89% Traditional cash on cash: 2.18% Airbnb Rental Income: $9228 Traditional Rental Income: $2574 Airbnb ROI: 9.89% Traditional ROI: 2.18%
29051 MAGNOLIA LANE Big Pine Key, FL Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front h...	3 beds \| 3 baths \| 1,344 sq.ft.	$1,055,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 2.94% Airbnb Rental Income: $9228 Traditional Rental Income: $4535 Airbnb ROI: 5.96% Traditional ROI: 2.94%
29284 Coconut Palm Drive Big Pine Key, FL Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush...	2 beds \| 1 baths \| 812 sq.ft.	$525,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.46% Airbnb Rental Income: $2687 Traditional Rental Income: $3141 Airbnb ROI: 2.23% Traditional ROI: 4.46%
30937 Baileys Lane Big Pine Key, FL Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the be...	3 beds \| 2 baths \| 1,980 sq.ft.	$849,000	Airbnb cash on cash: 7.77% Traditional cash on cash: 3.72% Airbnb Rental Income: $9228 Traditional Rental Income: $4295 Airbnb ROI: 7.77% Traditional ROI: 3.72%
31011 Avenue C Big Pine Key, FL New interior photos! This 4-bedroom, 2-bath, 1566 sq. ft. home in the Keys is a rare find ...	4 beds \| 2 baths \| 1,566 sq.ft.	$675,000	Airbnb cash on cash: 9.15% Traditional cash on cash: 5.18% Airbnb Rental Income: $8598 Traditional Rental Income: $4474 Airbnb ROI: 9.15% Traditional ROI: 5.18%
29635 Saratoga Avenue Big Pine Key, FL Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This bea...	3 beds \| 2 baths \| 1,396 sq.ft.	$1,550,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 0.54% Airbnb Rental Income: $9228 Traditional Rental Income: $3300 Airbnb ROI: 3.45% Traditional ROI: 0.54%
1657 Watson Boulevard Big Pine Key, FL Experience the keys waterfront lifestyle! This charming 3 bedroom, 2 bath home has peekabo...	3 beds \| 2 baths \| 1,330 sq.ft.	$1,275,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 2% Airbnb Rental Income: $9228 Traditional Rental Income: $4316 Airbnb ROI: 4.69% Traditional ROI: 2%
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: 9.64% Traditional cash on cash: 4.75% Airbnb Rental Income: $9228 Traditional Rental Income: $4186 Airbnb ROI: 9.64% Traditional ROI: 4.75%
1672 Pandorea Lane Big Pine Key, FL Discover canal-front living in Eden Pines Colony where local amenities are within easy rea...	2 beds \| 2 baths \| 912 sq.ft.	$799,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.25% Airbnb Rental Income: $2687 Traditional Rental Income: $3790 Airbnb ROI: 0.91% Traditional ROI: 3.25%
3962-3964 No Name Road Big Pine Key, FL Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD\|1BA on each side. Property features,...	4 beds \| 2 baths \| 1,536 sq.ft.	$987,500	Airbnb cash on cash: 5.97% Traditional cash on cash: 2.71% Airbnb Rental Income: $8598 Traditional Rental Income: $3973 Airbnb ROI: 5.97% Traditional ROI: 2.71%
30995 Watson Boulevard Big Pine Key, FL Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level re...	4 beds \| 3 baths \| 2,400 sq.ft.	$2,300,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 1.71% Airbnb Rental Income: $8598 Traditional Rental Income: $6314 Airbnb ROI: 2.02% Traditional ROI: 1.71%
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: 2.37% Traditional cash on cash: 1.28% Airbnb Rental Income: $9228 Traditional Rental Income: $5396 Airbnb ROI: 2.37% Traditional ROI: 1.28%
29562 Saratoga Avenue Big Pine Key, FL Embrace island living in your own tropical paradise, where comfort, space, and waterfront ...	4 beds \| 2 baths \| 2,310 sq.ft.	$1,435,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 1.1% Airbnb Rental Income: $8598 Traditional Rental Income: $3804 Airbnb ROI: 3.48% Traditional ROI: 1.1%
30525 Winifred Street Big Pine Key, FL Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in PO...	3 beds \| 3 baths \| 1,774 sq.ft.	$1,250,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 4.54% Airbnb Rental Income: $9228 Traditional Rental Income: $7247 Airbnb ROI: 4.76% Traditional ROI: 4.54%
216 Newfound Boulevard Big Pine Key, FL A true tropical oasis nestled on a 6,600 sq ft lot with lush landscaping and a mature mang...	3 beds \| 2 baths \| 1,360 sq.ft.	$900,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 3.62% Airbnb Rental Income: $9228 Traditional Rental Income: $4574 Airbnb ROI: 7.12% Traditional ROI: 3.62%
1540 Lantana Lane Big Pine Key, FL Bring your boats to this beautifully furnished canal front home. This home is secluded on ...	3 beds \| 2 baths \| 1,418 sq.ft.	$949,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 4.82% Airbnb Rental Income: $9228 Traditional Rental Income: $5883 Airbnb ROI: 6.66% Traditional ROI: 4.82%
30375 Oleander Boulevard Big Pine Key, FL Island Living in Big Pine Key! Charming and updated 2-bedroom, 1-bath concrete block home ...	2 beds \| 1 baths \| 816 sq.ft.	$549,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.64% Airbnb Rental Income: $2687 Traditional Rental Income: $1783 Airbnb ROI: 2.16% Traditional ROI: 1.64%
3922 Gordon Road Big Pine Key, FL Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordo...	2 beds \| 2 baths \| 1,040 sq.ft.	$799,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.47% Airbnb Rental Income: $2687 Traditional Rental Income: $3984 Airbnb ROI: 0.87% Traditional ROI: 3.47%
1136 W SHORE Drive Big Pine Key, FL Not a drive by- Must see inside and the back yard too. Located on the West Side of the Isl...	3 beds \| 4 baths \| 2,295 sq.ft.	$1,599,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.96% Airbnb Rental Income: $9228 Traditional Rental Income: $8717 Airbnb ROI: 3.15% Traditional ROI: 3.96%
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: 0.9% Traditional cash on cash: 3.07% Airbnb Rental Income: $2687 Traditional Rental Income: $3751 Airbnb ROI: 0.9% Traditional ROI: 3.07%
30468 Oleander Boulevard Big Pine Key, FL Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuri...	3 beds \| 3 baths \| 2,486 sq.ft.	$2,150,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 1.6% Airbnb Rental Income: $9228 Traditional Rental Income: $6518 Airbnb ROI: 2.1% Traditional ROI: 1.6%
30368 Killdeer Lane Big Pine Key, FL Welcome to island living in Big Pine Key. Situated on a desirable corner lot, this beautif...	3 beds \| 2 baths \| 1,200 sq.ft.	$964,999	Airbnb cash on cash: 6.59% Traditional cash on cash: 2.94% Airbnb Rental Income: $9228 Traditional Rental Income: $4223 Airbnb ROI: 6.59% Traditional ROI: 2.94%
29662 Independence Avenue Big Pine Key, FL DOUBLE LOT waterfront opportunity in Big Pine Key! This charming 2 bedroom, 2 bathroom hom...	2 beds \| 2 baths \| 1,024 sq.ft.	$1,199,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.06% Airbnb Rental Income: $2687 Traditional Rental Income: $3882 Airbnb ROI: 0.41% Traditional ROI: 2.06%
29115 Rose Drive Big Pine Key, FL Back on the market! Welcome to this meticulously maintained and updated move-in ready cana...	3 beds \| 2 baths \| 1,250 sq.ft.	$825,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.25% Airbnb Rental Income: $9228 Traditional Rental Income: $4301 Airbnb ROI: 8.41% Traditional ROI: 4.25%
31135 Hollerich Drive Big Pine Key, FL A beautifully kept home with amazing views of the Gulf, and easy boating access to some of...	2 beds \| 2 baths \| 1,313 sq.ft.	$1,099,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.56% Airbnb Rental Income: $2687 Traditional Rental Income: $4293 Airbnb ROI: 0.36% Traditional ROI: 2.56%
3742 Seagrape Street Big Pine Key, FL Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres o...	3 beds \| 3 baths \| 4,687 sq.ft.	$4,995,000	Airbnb cash on cash: -0.01% Traditional cash on cash: -0.3% Airbnb Rental Income: $9228 Traditional Rental Income: $6139 Airbnb ROI: -0.01% Traditional ROI: -0.3%
1433 Sunset Road Big Pine Key, FL 699,000 for 2 units. Great price reduction on income producing CBS duplex in Big Pine Key....	4 beds \| 3 baths \| 1,924 sq.ft.	$699,000	Airbnb cash on cash: 8.71% Traditional cash on cash: 5.48% Airbnb Rental Income: $8598 Traditional Rental Income: $4870 Airbnb ROI: 8.71% Traditional ROI: 5.48%
31473 Warner Road Big Pine Key, FL Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of moder...	3 beds \| 4 baths \| 2,087 sq.ft.	$2,450,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 1.01% Airbnb Rental Income: $9228 Traditional Rental Income: $6082 Airbnb ROI: 1.64% Traditional ROI: 1.01%
31449 Avenue I Big Pine Key, FL Dolphinus del Sol is a Waterfront Estate Masterpiece! Enjoy this custom, ultra-modern smar...	5 beds \| 4 baths \| 3,500 sq.ft.	$4,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.34% Airbnb Rental Income: $null Traditional Rental Income: $6488 Airbnb ROI: N/A Traditional ROI: 0.34%
2211 San Sebastian Drive Big Pine Key, FL Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected de...	4 beds \| 3 baths \| 2,000 sq.ft.	$1,700,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.03% Airbnb Rental Income: $8598 Traditional Rental Income: $5199 Airbnb ROI: 3.16% Traditional ROI: 2.03%
1634 Lantana Lane Big Pine Key, FL Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-a...	2 beds \| 2 baths \| 1,152 sq.ft.	$799,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.27% Airbnb Rental Income: $2687 Traditional Rental Income: $3861 Airbnb ROI: 0.84% Traditional ROI: 3.27%
31033 Hibiscus Drive Big Pine Key, FL Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Ke...	3 beds \| 2 baths \| 1,008 sq.ft.	$750,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 4.42% Airbnb Rental Income: $9228 Traditional Rental Income: $4061 Airbnb ROI: 9.34% Traditional ROI: 4.42%
31478 Avenue E Big Pine Key, FL PRICED RIGHT RESORT SETTING Adorable charm and the essential Florida Keys lifestyle ca...	1 beds \| 1 baths \| 557 sq.ft.	$509,999	Airbnb cash on cash: 1.01% Traditional cash on cash: 4.19% Airbnb Rental Income: $1991 Traditional Rental Income: $2985 Airbnb ROI: 1.01% Traditional ROI: 4.19%
1553 Sunrise Drive Big Pine Key, FL Walk into this luxurious palace with captivating open water views. Light colors accenting ...	3 beds \| 3 baths \| 2,100 sq.ft.	$2,700,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.05% Airbnb Rental Income: $9228 Traditional Rental Income: $6142 Airbnb ROI: 1.6% Traditional ROI: 1.05%
30374 Oleander Boulevard Big Pine Key, FL If you want a spacious home with plenty of privacy, this property delivers. Set within a l...	4 beds \| 2 baths \| 2,136 sq.ft.	$763,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 5.45% Airbnb Rental Income: $8598 Traditional Rental Income: $5225 Airbnb ROI: 7.91% Traditional ROI: 5.45%

Real Estate investment in Big-pine-key, FL

There are 49 properties for sale in the city of Big Pine Key . The median list price in Big Pine Key is $634,672 and the average price per square foot is $414. In June 2026, the average monthly cash on cash return in Big Pine Key is 2.00%. The average monthly rental income in Big Pine Key is $3,209.

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

There are 49 investment properties available for sale in Big-pine-key.

In 2026, 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 $8,598.

Your search for investment property begins and ends here

Investment Property for Sale in Big Pine Key, FL

29034 Rose Drive

Big Pine Key, FL

2 beds | 1 baths | 864 sq.ft.

$795,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2687

Traditional Rental Income: $4559

Airbnb ROI: 0.9%

Traditional ROI: 4.29%

3746 Park Avenue

Big Pine Key, FL

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

$1,399,900

Airbnb cash on cash: -0.05%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $2687

Traditional Rental Income: $4285

Airbnb ROI: -0.05%

Traditional ROI: 1.67%

29175 Violet Drive

Big Pine Key, FL

3 beds | 2 baths | 986 sq.ft.

$685,000

Airbnb cash on cash: 9.89%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $9228

Traditional Rental Income: $2574

Airbnb ROI: 9.89%

Traditional ROI: 2.18%

29051 MAGNOLIA LANE

Big Pine Key, FL

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

$1,055,000

Airbnb cash on cash: 5.96%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $9228

Traditional Rental Income: $4535

Airbnb ROI: 5.96%

Traditional ROI: 2.94%

29284 Coconut Palm Drive

Big Pine Key, FL

2 beds | 1 baths | 812 sq.ft.

$525,000

Airbnb cash on cash: 2.23%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2687

Traditional Rental Income: $3141

Airbnb ROI: 2.23%

Traditional ROI: 4.46%

30937 Baileys Lane

Big Pine Key, FL

3 beds | 2 baths | 1,980 sq.ft.

$849,000

Airbnb cash on cash: 7.77%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $9228

Traditional Rental Income: $4295

Airbnb ROI: 7.77%

Traditional ROI: 3.72%

31011 Avenue C

Big Pine Key, FL

4 beds | 2 baths | 1,566 sq.ft.

$675,000

Airbnb cash on cash: 9.15%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $8598

Traditional Rental Income: $4474

Airbnb ROI: 9.15%

Traditional ROI: 5.18%

29635 Saratoga Avenue

Big Pine Key, FL

3 beds | 2 baths | 1,396 sq.ft.

$1,550,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 0.54%

Airbnb Rental Income: $9228

Traditional Rental Income: $3300

Airbnb ROI: 3.45%