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.	$785,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 4.36% Airbnb Rental Income: $3624 Traditional Rental Income: $4559 Airbnb ROI: 1.99% Traditional ROI: 4.36%
2131 Coral Way Big Pine Key, FL SPECTACULAR OPEN-WATER VIEWS AND PROTECTED CANAL FRONTAGE WITH A BOAT HOUSE! Experience th...	4 beds \| 4 baths \| 2,100 sq.ft.	$2,750,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.89% Airbnb Rental Income: $8598 Traditional Rental Income: $8924 Airbnb ROI: 1.12% Traditional ROI: 1.89%
30354 Palm Drive Big Pine Key, FL Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2B...	2 beds \| 2 baths \| 1,030 sq.ft.	$499,999	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.05% Airbnb Rental Income: $3624 Traditional Rental Income: $2374 Airbnb ROI: 4.03% Traditional ROI: 3.05%
3746 Park Avenue Big Pine Key, FL SELLER WILL GIVE A $20,000.00 BUYER CLOSING CREDIT! Welcome to your private paradise in th...	2 beds \| 2 baths \| 1,312 sq.ft.	$1,099,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.39% Airbnb Rental Income: $3624 Traditional Rental Income: $4285 Airbnb ROI: 0.97% Traditional ROI: 2.39%
1669 Lantana Lane Big Pine Key, FL This beautifully updated 2 bedroom, 2 bathroom home sits on an oversized lot and offers th...	2 beds \| 2 baths \| 988 sq.ft.	$895,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 1.48% Airbnb Rental Income: $3624 Traditional Rental Income: $2628 Airbnb ROI: 1.72% Traditional ROI: 1.48%
1632 Bogie Drive Big Pine Key, FL Welcome to your tropical Keys retreat on a huge double lot totaling nearly half an acre--p...	3 beds \| 4 baths \| 1,508 sq.ft.	$1,164,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 1.55% Airbnb Rental Income: $9228 Traditional Rental Income: $3604 Airbnb ROI: 5.15% Traditional ROI: 1.55%
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.	$1,450,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 0.64% Airbnb Rental Income: $9228 Traditional Rental Income: $3300 Airbnb ROI: 3.76% Traditional ROI: 0.64%
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.	$1,150,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 2.32% Airbnb Rental Income: $9228 Traditional Rental Income: $4316 Airbnb ROI: 5.3% Traditional ROI: 2.32%
30363 Flamingo Lane Big Pine Key, FL Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete w...	4 beds \| 3 baths \| 2,136 sq.ft.	$1,695,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 1.73% Airbnb Rental Income: $8598 Traditional Rental Income: $5132 Airbnb ROI: 2.9% Traditional ROI: 1.73%
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.	$925,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 2.91% Airbnb Rental Income: $8598 Traditional Rental Income: $3973 Airbnb ROI: 6.4% Traditional ROI: 2.91%
1733 Sunrise Dr Big Pine Key, FL Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and ...	3 beds \| 2 baths \| 1,849 sq.ft.	$1,970,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 1.39% Airbnb Rental Income: $9228 Traditional Rental Income: $5396 Airbnb ROI: 2.54% Traditional ROI: 1.39%
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%
31357 Avenue C Big Pine Key, FL Bring your vision and make this Big Pine Key property your own! Situated on two spacious, ...	3 beds \| 2 baths \| 1,451 sq.ft.	$748,516	Airbnb cash on cash: 8.91% Traditional cash on cash: 6.16% Airbnb Rental Income: $9228 Traditional Rental Income: $5584 Airbnb ROI: 8.91% Traditional ROI: 6.16%
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.	$1,125,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 5.15% Airbnb Rental Income: $9228 Traditional Rental Income: $7247 Airbnb ROI: 5.39% Traditional ROI: 5.15%
31490 Avenue F Big Pine Key, FL Brand-New Waterfront Home in the Florida Keys Discover the ultimate Florida Keys lifestyle...	3 beds \| 3 baths \| 1,654 sq.ft.	$950,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 3.68% Airbnb Rental Income: $9228 Traditional Rental Income: $4935 Airbnb ROI: 6.58% Traditional ROI: 3.68%
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.	$899,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 5.15% Airbnb Rental Income: $9228 Traditional Rental Income: $5883 Airbnb ROI: 7.08% Traditional ROI: 5.15%
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.	$539,900	Airbnb cash on cash: 3.76% Traditional cash on cash: 1.69% Airbnb Rental Income: $3624 Traditional Rental Income: $1783 Airbnb ROI: 3.76% Traditional ROI: 1.69%
31507 Avenue E Big Pine Key, FL Experience waterfront living in Big Pine Key at this striking coastal residence, positione...	3 beds \| 2 baths \| 1,140 sq.ft.	$1,300,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 0.73% Airbnb Rental Income: $9228 Traditional Rental Income: $2821 Airbnb ROI: 4.61% Traditional ROI: 0.73%
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: 1.9% Traditional cash on cash: 3.07% Airbnb Rental Income: $3624 Traditional Rental Income: $3751 Airbnb ROI: 1.9% 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.	$925,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 3.11% Airbnb Rental Income: $9228 Traditional Rental Income: $4223 Airbnb ROI: 6.92% Traditional ROI: 3.11%
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: 1.13% Traditional cash on cash: 2.56% Airbnb Rental Income: $3624 Traditional Rental Income: $4293 Airbnb ROI: 1.13% Traditional ROI: 2.56%
31450 Avenue G Big Pine Key, FL Exclusive New Construction in Big Pine Key, Florida Discover the perfect blend of modern l...	4 beds \| 3 baths \| 2,323 sq.ft.	$1,750,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 2.17% Airbnb Rental Income: $8598 Traditional Rental Income: $6051 Airbnb ROI: 2.74% Traditional ROI: 2.17%
31569 Avenue D Big Pine Key, FL Brand-New Waterfront Luxury Home in the Florida Keys Discover the ultimate Florida Keys li...	4 beds \| 3 baths \| 1,896 sq.ft.	$1,200,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 3.35% Airbnb Rental Income: $8598 Traditional Rental Income: $5176 Airbnb ROI: 4.96% Traditional ROI: 3.35%
31441 Avenue F Big Pine Key, FL Brand-New Waterfront Home in the Florida Keys Discover the perfect blend of modern luxury ...	4 beds \| 3 baths \| 1,458 sq.ft.	$975,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 3.72% Airbnb Rental Income: $8598 Traditional Rental Income: $4631 Airbnb ROI: 6.3% Traditional ROI: 3.72%
1518 Sunrise Drive Big Pine Key, FL Discover your paradise in the heart of Big Pine Key! This beautifully maintained 3-bedroom...	3 beds \| 2 baths \| 1,540 sq.ft.	$1,400,000	Airbnb cash on cash: 4.13% Traditional cash on cash: -0.08% Airbnb Rental Income: $9228 Traditional Rental Income: $2018 Airbnb ROI: 4.13% Traditional ROI: -0.08%
29486 Ranger Avenue Big Pine Key, FL Your Florida Keys lifestyle is calling! This newly updated Big Pine Key home offers 3 bedr...	3 beds \| 2 baths \| 1,320 sq.ft.	$1,200,000	Airbnb cash on cash: 5% Traditional cash on cash: 0.51% Airbnb Rental Income: $9228 Traditional Rental Income: $2492 Airbnb ROI: 5% Traditional ROI: 0.51%
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.	$4,450,000	Airbnb cash on cash: 0.11% Traditional cash on cash: -0.22% Airbnb Rental Income: $9228 Traditional Rental Income: $6139 Airbnb ROI: 0.11% Traditional ROI: -0.22%
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 Waterfront views of mesmerizing sunrises and moonrises. Imagine having your own private do...	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%
31478 Avenue E Big Pine Key, FL Check out this Price Improvement!!! Adorable charm and the essential Florida Keys lifestyl...	1 beds \| 1 baths \| 557 sq.ft.	$460,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 4.75% Airbnb Rental Income: $2103 Traditional Rental Income: $2985 Airbnb ROI: 1.45% Traditional ROI: 4.75%
30374 Oleander Boulevard Big Pine Key, FL This spacious Big Pine Key home is situated on a lushly landscaped 12,500 sq. ft. double 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.	$729,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 3.71% Airbnb Rental Income: $3624 Traditional Rental Income: $3614 Airbnb ROI: 2.56% Traditional ROI: 3.71%
29565 Flying Cloud Ave Big Pine Key, FL Waterfront retreat with excellent boating access in the heart of Big Pine Key! Home has 15...	4 beds \| 3 baths \| 960 sq.ft.	$1,100,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 1.02% Airbnb Rental Income: $8598 Traditional Rental Income: $2877 Airbnb ROI: 5.03% Traditional ROI: 1.02%
29424 Forrestal Avenue Big Pine Key, FL If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished ...	3 beds \| 2 baths \| 1,392 sq.ft.	$1,550,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 0.7% Airbnb Rental Income: $9228 Traditional Rental Income: $3313 Airbnb ROI: 3.61% Traditional ROI: 0.7%
29678 Enterprise Avenue Big Pine Key, FL Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex ...	4 beds \| 2 baths \| 1,820 sq.ft.	$1,295,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 1.77% Airbnb Rental Income: $9228 Traditional Rental Income: $3980 Airbnb ROI: 4.69% Traditional ROI: 1.77%
31032 Hollerich Drive Big Pine Key, FL Waterfront Duplex with Income Potential in Big Pine Key! Live the Florida Keys lifestyle w...	4 beds \| 2 baths \| 1,460 sq.ft.	$825,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 3.02% Airbnb Rental Income: $9228 Traditional Rental Income: $3346 Airbnb ROI: 8.43% Traditional ROI: 3.02%

Real Estate investment in Big-pine-key, FL

There are 41 properties for sale in the city of Big Pine Key . The median list price in Big Pine Key is $964,541 and the average price per square foot is $625. In November 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 $3,207.

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

There are 41 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.

$785,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $3624

Traditional Rental Income: $4559

Airbnb ROI: 1.99%

Traditional ROI: 4.36%

2131 Coral Way

Big Pine Key, FL

4 beds | 4 baths | 2,100 sq.ft.

$2,750,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $8598

Traditional Rental Income: $8924

Airbnb ROI: 1.12%

Traditional ROI: 1.89%

30354 Palm Drive

Big Pine Key, FL

2 beds | 2 baths | 1,030 sq.ft.

$499,999

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $3624

Traditional Rental Income: $2374

Airbnb ROI: 4.03%

Traditional ROI: 3.05%

3746 Park Avenue

Big Pine Key, FL

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

$1,099,900

Airbnb cash on cash: 0.97%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $3624

Traditional Rental Income: $4285

Airbnb ROI: 0.97%

Traditional ROI: 2.39%

1669 Lantana Lane

Big Pine Key, FL

2 beds | 2 baths | 988 sq.ft.

$895,000

Airbnb cash on cash: 1.72%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $3624

Traditional Rental Income: $2628

Airbnb ROI: 1.72%

Traditional ROI: 1.48%

1632 Bogie Drive

Big Pine Key, FL

3 beds | 4 baths | 1,508 sq.ft.

$1,164,000

Airbnb cash on cash: 5.15%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $9228

Traditional Rental Income: $3604

Airbnb ROI: 5.15%

Traditional ROI: 1.55%

29635 Saratoga Avenue

Big Pine Key, FL

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

$1,450,000

Airbnb cash on cash: 3.76%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $9228

Traditional Rental Income: $3300

Airbnb ROI: 3.76%

Traditional ROI: 0.64%

1657 Watson Boulevard

Big Pine Key, FL

3 beds | 2 baths | 1,330 sq.ft.

$1,150,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $9228

Traditional Rental Income: $4316

Airbnb ROI: 5.3%