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 40 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
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: 8.48% Traditional cash on cash: 3.87% Airbnb Rental Income: $9228 Traditional Rental Income: $4130 Airbnb ROI: 8.48% Traditional ROI: 3.87%
29961 Pine Channel Road Big Pine Key, FL Welcome to your perfect Florida Keys getaway in the heart of Big Pine Key. This charming 2...	2 beds \| 1 baths \| 850 sq.ft.	$595,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 3.58% Airbnb Rental Income: $6343 Traditional Rental Income: $3066 Airbnb ROI: 7.24% Traditional ROI: 3.58%
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: 2.29% Traditional cash on cash: 1.67% Airbnb Rental Income: $6343 Traditional Rental Income: $4285 Airbnb ROI: 2.29% 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%
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: 3.46% Traditional cash on cash: 0.54% Airbnb Rental Income: $9228 Traditional Rental Income: $3300 Airbnb ROI: 3.46% 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: 5% Traditional cash on cash: 3.25% Airbnb Rental Income: $6343 Traditional Rental Income: $3790 Airbnb ROI: 5% Traditional ROI: 3.25%
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: 1.71% Airbnb Rental Income: $8598 Traditional Rental Income: $6314 Airbnb ROI: 2.02% Traditional ROI: 1.71%
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%
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.	$989,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 4.59% Airbnb Rental Income: $9228 Traditional Rental Income: $5883 Airbnb ROI: 6.35% Traditional ROI: 4.59%
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: 8.09% Traditional cash on cash: 1.64% Airbnb Rental Income: $6343 Traditional Rental Income: $1783 Airbnb ROI: 8.09% Traditional ROI: 1.64%
29048 Iris Drive Big Pine Key, FL 50' wide canal provides great boat access to the Atlantic and back country via Pine Channe...	3 beds \| 2 baths \| 1,039 sq.ft.	$698,800	Airbnb cash on cash: 9.62% Traditional cash on cash: 4.52% Airbnb Rental Income: $9228 Traditional Rental Income: $4179 Airbnb ROI: 9.62% Traditional ROI: 4.52%
3922 Gordon Road Big Pine Key, FL Seller is offering a $15,000 credit toward an interest rate buydown for qualified buyers o...	2 beds \| 2 baths \| 1,040 sq.ft.	$845,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 3.22% Airbnb Rental Income: $6343 Traditional Rental Income: $3984 Airbnb ROI: 4.64% Traditional ROI: 3.22%
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: 4.79% Traditional cash on cash: 3.07% Airbnb Rental Income: $6343 Traditional Rental Income: $3751 Airbnb ROI: 4.79% 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.	$979,999	Airbnb cash on cash: 6.47% Traditional cash on cash: 2.88% Airbnb Rental Income: $9228 Traditional Rental Income: $4223 Airbnb ROI: 6.47% Traditional ROI: 2.88%
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.	$1,199,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.06% Airbnb Rental Income: $6343 Traditional Rental Income: $3882 Airbnb ROI: 3.15% Traditional ROI: 2.06%
30416 Coconut Highway Big Pine Key, FL Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft...	2 beds \| 2 baths \| 1,497 sq.ft.	$665,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 5.19% Airbnb Rental Income: $6343 Traditional Rental Income: $4063 Airbnb ROI: 6.85% Traditional ROI: 5.19%
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.	$1,149,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.4% Airbnb Rental Income: $6343 Traditional Rental Income: $4293 Airbnb ROI: 3.15% Traditional ROI: 2.4%
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.	$5,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.25% Airbnb Rental Income: $null Traditional Rental Income: $6488 Airbnb ROI: N/A Traditional ROI: 0.25%
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: 4.93% Traditional cash on cash: 3.27% Airbnb Rental Income: $6343 Traditional Rental Income: $3861 Airbnb ROI: 4.93% 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 OPEN HOUSE SAT FEB 7TH 12-2Discover the quintessential Florida Keys lifestyle in this...	1 beds \| 1 baths \| 557 sq.ft.	$525,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 4.04% Airbnb Rental Income: $3882 Traditional Rental Income: $2985 Airbnb ROI: 4.17% Traditional ROI: 4.04%
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%
30830 Palm Drive Big Pine Key, FL Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an overs...	3 beds \| 2 baths \| 2,556 sq.ft.	$1,385,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.09% Airbnb Rental Income: $9228 Traditional Rental Income: $5873 Airbnb ROI: 4.35% Traditional ROI: 3.09%
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: 5.45% Traditional cash on cash: 3.41% Airbnb Rental Income: $6343 Traditional Rental Income: $3614 Airbnb ROI: 5.45% Traditional ROI: 3.41%
1547 Gardenia Lane Big Pine Key, FL Coastal Retreat in Florida Keys. Stunning new construction canal-front,island living. Situ...	4 beds \| 3 baths \| 1,900 sq.ft.	$1,125,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.01% Airbnb Rental Income: $8598 Traditional Rental Income: $5623 Airbnb ROI: 5.3% Traditional ROI: 4.01%
1112 W Shore Drive Big Pine Key, FL Experience elevated coastal luxury in this stunning CBS waterfront home in highly desirabl...	4 beds \| 3 baths \| 2,330 sq.ft.	$2,449,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 0.52% Airbnb Rental Income: $8598 Traditional Rental Income: $4556 Airbnb ROI: 1.58% Traditional ROI: 0.52%
29131 Watson Boulevard Big Pine Key, FL Peaceful serenity found on this 22,077 square foot property with a cozy two bedroom one an...	2 beds \| 2 baths \| 960 sq.ft.	$995,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 1.28% Airbnb Rental Income: $6343 Traditional Rental Income: $2496 Airbnb ROI: 4.09% Traditional ROI: 1.28%
29555 Enterprise Avenue Big Pine Key, FL Welcome to your Lower Keys retreat where comfort, and coastal living come together beautif...	3 beds \| 3 baths \| 1,352 sq.ft.	$1,100,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 1.35% Airbnb Rental Income: $9228 Traditional Rental Income: $3207 Airbnb ROI: 5.54% Traditional ROI: 1.35%
30361 Hardin Road Big Pine Key, FL 270' OF CANAL FRONTAGE & TWO CONCRETE DOCKS (70' + 54') - DOUBLE LOT - Welcome to the Blue...	3 beds \| 2 baths \| 888 sq.ft.	$749,900	Airbnb cash on cash: 9.24% Traditional cash on cash: 2.36% Airbnb Rental Income: $9228 Traditional Rental Income: $2690 Airbnb ROI: 9.24% Traditional ROI: 2.36%

Your search for investment property begins and ends here

Single Family Homes for Sale in Big Pine Key, FL

29850 Journeys End Road

Big Pine Key, FL

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

$785,000

Airbnb cash on cash: 8.48%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $9228

Traditional Rental Income: $4130

Airbnb ROI: 8.48%

Traditional ROI: 3.87%

29961 Pine Channel Road

Big Pine Key, FL

2 beds | 1 baths | 850 sq.ft.

$595,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $6343

Traditional Rental Income: $3066

Airbnb ROI: 7.24%

Traditional ROI: 3.58%

3746 Park Avenue

Big Pine Key, FL

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

$1,399,900

Airbnb cash on cash: 2.29%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $6343

Traditional Rental Income: $4285

Airbnb ROI: 2.29%

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%

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: 3.46%

Traditional cash on cash: 0.54%

Airbnb Rental Income: $9228

Traditional Rental Income: $3300

Airbnb ROI: 3.46%

Traditional ROI: 0.54%

1657 Watson Boulevard

Big Pine Key, FL

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%