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
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%
3962-3964 No Name Road Big Pine Key, FL Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD\|1BA on each side. Property feature...	4 beds \| 2 baths \| 1,536 sq.ft.	$987,500	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.71% Airbnb Rental Income: $6343 Traditional Rental Income: $3973 Airbnb ROI: 3.93% Traditional ROI: 2.71%
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%
29859 Overseas Highway #UNIT 37 Big Pine Key, FL Welcome to easy island living in this 2021 Skyline Park Model Home located in the desirabl...	1 beds \| 1 baths \| 312 sq.ft.	$269,999	Airbnb cash on cash: 9.84% Traditional cash on cash: 9.07% Airbnb Rental Income: $3882 Traditional Rental Income: $2849 Airbnb ROI: 9.84% Traditional ROI: 9.07%
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%
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: 2.34% Traditional cash on cash: 5.51% Airbnb Rental Income: $3588 Traditional Rental Income: $4870 Airbnb ROI: 2.34% Traditional ROI: 5.51%
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%

Real Estate investment in Big-pine-key, FL

There are 43 properties for sale in the city of Big Pine Key . The median list price in Big Pine Key is $940,000 and the average price per square foot is $605. In May 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 $3,206.

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

There are 43 investment properties available for sale in 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

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%