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.

Single Family Homes for Sale in Big Pine Key, FL

Search for Single Family Residential for Sale in Big Pine Key, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 46 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
1719 Narcissus Avenue Big Pine Key, FL Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home i...	2 beds \| 2 baths \| 912 sq.ft.	$779,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.41% Airbnb Rental Income: $2687 Traditional Rental Income: $3614 Airbnb ROI: 1.25% Traditional ROI: 3.41%

Your search for investment property begins and ends here

Single Family Homes 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%