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: 1.8% Airbnb Rental Income: $9228 Traditional Rental Income: $2615 Airbnb ROI: 8.48% Traditional ROI: 1.8%
3746 Park Avenue Big Pine Key, FL Welcome to your private paradise in the Lower Keys! This beautifully updated 2 bed, 2 bath...	2 beds \| 2 baths \| 1,312 sq.ft.	$1,850,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.28% Airbnb Rental Income: $2049 Traditional Rental Income: $3006 Airbnb ROI: -0.59% Traditional ROI: 0.28%
29051 Magnolia Ln Big Pine Key, FL Welcome to 29051 Magnolia Ln, Big Pine Key, FL! This home offers a 2-bedroom, 2-bath main ...	3 beds \| 3 baths \| 1,344 sq.ft.	$1,099,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 1.62% Airbnb Rental Income: $9228 Traditional Rental Income: $3346 Airbnb ROI: 5.68% Traditional ROI: 1.62%
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.	$1,399,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 0.92% Airbnb Rental Income: $9228 Traditional Rental Income: $3255 Airbnb ROI: 4.18% Traditional ROI: 0.92%
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: 3.09% Airbnb Rental Income: $9228 Traditional Rental Income: $3063 Airbnb ROI: 9.64% Traditional ROI: 3.09%
29523 Enterprise Avenue Big Pine Key, FL Welcome to effortless waterfront living in the heart of Big Pine Key. This updated canal-f...	3 beds \| 2 baths \| 1,539 sq.ft.	$1,080,000	Airbnb cash on cash: 5.63% Traditional cash on cash: 3.29% Airbnb Rental Income: $9228 Traditional Rental Income: $5145 Airbnb ROI: 5.63% Traditional ROI: 3.29%
30363 Flamingo Lane Big Pine Key, FL Tranquility meets coastal living, discover this stunning concrete constructed home built i...	3 beds \| 3 baths \| 1,837 sq.ft.	$1,785,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 0.89% Airbnb Rental Income: $9228 Traditional Rental Income: $3928 Airbnb ROI: 3.05% Traditional ROI: 0.89%
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: 0.19% Traditional cash on cash: 1.8% Airbnb Rental Income: $2049 Traditional Rental Income: $2716 Airbnb ROI: 0.19% Traditional ROI: 1.8%
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: 0.04% Traditional cash on cash: 2.28% Airbnb Rental Income: $2049 Traditional Rental Income: $3583 Airbnb ROI: 0.04% Traditional ROI: 2.28%
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: 0.71% Airbnb Rental Income: $8598 Traditional Rental Income: $4183 Airbnb ROI: 2.02% Traditional ROI: 0.71%
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: 0.62% Airbnb Rental Income: $9228 Traditional Rental Income: $4128 Airbnb ROI: 2.37% Traditional ROI: 0.62%
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.	$274,999	Airbnb cash on cash: 1.34% Traditional cash on cash: 7.92% Airbnb Rental Income: $1296 Traditional Rental Income: $2599 Airbnb ROI: 1.34% Traditional ROI: 7.92%
550 Pine Lane Big Pine Key, FL This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot ...	3 beds \| 1 baths \| 1,043 sq.ft.	$849,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 1.41% Airbnb Rental Income: $9228 Traditional Rental Income: $2522 Airbnb ROI: 7.7% Traditional ROI: 1.41%
31490 Avenue F Big Pine Key, FL This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and f...	3 beds \| 3 baths \| 1,492 sq.ft.	$975,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 4.78% Airbnb Rental Income: $9228 Traditional Rental Income: $5960 Airbnb ROI: 6.48% Traditional ROI: 4.78%
30366 Falcon Lane Big Pine Key, FL Fantastic CBS canal front Pool home on a double lot in Tropical Bay Estates. Entering int...	3 beds \| 2 baths \| 1,398 sq.ft.	$1,199,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 2.9% Airbnb Rental Income: $9228 Traditional Rental Income: $5066 Airbnb ROI: 5.08% Traditional ROI: 2.9%
3 W COOK Big Pine Key, FL Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfron...	2 beds \| 2 baths \| 750 sq.ft.	$489,500	Airbnb cash on cash: 1.52% Traditional cash on cash: 3.18% Airbnb Rental Income: $2049 Traditional Rental Income: $2277 Airbnb ROI: 1.52% Traditional ROI: 3.18%
1136 W SHORE Drive Big Pine Key, FL Don't miss out on this home... It is NOT a drive by.....Located on the West Side of the Is...	3 beds \| 4 baths \| 2,295 sq.ft.	$1,849,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.29% Airbnb Rental Income: $9228 Traditional Rental Income: $5044 Airbnb ROI: 2.72% Traditional ROI: 1.29%
3672 Fox Street Big Pine Key, FL Discover a peaceful Keys escape on a quiet canal in Big Pine Key. This attractive 3-bedroo...	3 beds \| 3 baths \| 1,224 sq.ft.	$825,000	Airbnb cash on cash: 8.53% Traditional cash on cash: 3.14% Airbnb Rental Income: $9228 Traditional Rental Income: $3358 Airbnb ROI: 8.53% Traditional ROI: 3.14%
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: 0.22% Traditional cash on cash: 1.45% Airbnb Rental Income: $2049 Traditional Rental Income: $2479 Airbnb ROI: 0.22% Traditional ROI: 1.45%
29559 Ranger Avenue Big Pine Key, FL This well desired location and immaculately maintained home is 5 minutes from world class ...	2 beds \| 3 baths \| 1,200 sq.ft.	$999,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 1.97% Airbnb Rental Income: $2049 Traditional Rental Income: $3146 Airbnb ROI: 0.22% Traditional ROI: 1.97%
1607 Sunrise Drive Big Pine Key, FL Open water pool home with breathtaking views of Bogie Channel and direct deep water access...	2 beds \| 2 baths \| 1,980 sq.ft.	$1,699,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.12% Airbnb Rental Income: $2049 Traditional Rental Income: $2371 Airbnb ROI: -0.66% Traditional ROI: -0.12%
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.	$2,450,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 0.58% Airbnb Rental Income: $9228 Traditional Rental Income: $4923 Airbnb ROI: 1.72% Traditional ROI: 0.58%
30246 Watson Boulevard Big Pine Key, FL Discover your dream home on Big Pine Key at this expansive 37,500 sq. ft., property totali...	3 beds \| 2 baths \| 1,193 sq.ft.	$749,000	Airbnb cash on cash: 9.2% Traditional cash on cash: 2.16% Airbnb Rental Income: $9228 Traditional Rental Income: $2588 Airbnb ROI: 9.2% Traditional ROI: 2.16%
30985 Hibiscus Drive Big Pine Key, FL CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning sta...	4 beds \| 3 baths \| 2,166 sq.ft.	$1,250,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 2.36% Airbnb Rental Income: $8598 Traditional Rental Income: $4771 Airbnb ROI: 4.25% Traditional ROI: 2.36%
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.	$1,250,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.83% Airbnb Rental Income: $2049 Traditional Rental Income: $2580 Airbnb ROI: -0.08% Traditional ROI: 0.83%
29115 Rose Drive Big Pine Key, FL Welcome to this meticulously maintained and updated move-in ready canal-front home that of...	3 beds \| 2 baths \| 1,250 sq.ft.	$837,500	Airbnb cash on cash: 8.27% Traditional cash on cash: 2.43% Airbnb Rental Income: $9228 Traditional Rental Income: $2943 Airbnb ROI: 8.27% Traditional ROI: 2.43%
29859 Overseas Highway #UNIT A-6 Big Pine Key, FL Own a Piece of Paradise - A Renovator's Dream!Embrace the possibilities with this project ...	2 beds \| 2 baths \| 780 sq.ft.	$224,890	Airbnb cash on cash: 4.78% Traditional cash on cash: 7.49% Airbnb Rental Income: $2049 Traditional Rental Income: $2096 Airbnb ROI: 4.78% Traditional ROI: 7.49%
30416 Coconut Highway Big Pine Key, FL This 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV,...	2 beds \| 1 baths \| 1,497 sq.ft.	$718,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 2.18% Airbnb Rental Income: $2049 Traditional Rental Income: $2351 Airbnb ROI: 0.93% Traditional ROI: 2.18%
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.	$1,199,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.16% Airbnb Rental Income: $2049 Traditional Rental Income: $3032 Airbnb ROI: -0.2% Traditional ROI: 1.16%
31450 Avenue G Big Pine Key, FL This expansive 4 bedroom, 3 bathroom home offers over 2,300 sq ft of solid concrete constr...	4 beds \| 3 baths \| 2,323 sq.ft.	$1,789,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.01% Airbnb Rental Income: $8598 Traditional Rental Income: $4139 Airbnb ROI: 2.72% Traditional ROI: 1.01%
31569 Avenue D Big Pine Key, FL Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete h...	4 beds \| 3 baths \| 1,896 sq.ft.	$1,189,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.13% Airbnb Rental Income: $8598 Traditional Rental Income: $3791 Airbnb ROI: 5.02% Traditional ROI: 2.13%
31441 Avenue F Big Pine Key, FL This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the p...	4 beds \| 3 baths \| 1,457 sq.ft.	$980,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 1.86% Airbnb Rental Income: $8598 Traditional Rental Income: $2968 Airbnb ROI: 6.26% Traditional ROI: 1.86%
3742 Seagrape Street Big Pine Key, FL Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front...	3 beds \| 3 baths \| 4,687 sq.ft.	$5,900,000	Airbnb cash on cash: -0.12% Traditional cash on cash: -0.79% Airbnb Rental Income: $9228 Traditional Rental Income: $3839 Airbnb ROI: -0.12% Traditional ROI: -0.79%
31034 Hollerich Drive Big Pine Key, FL A great investment opportunity, or the chance for your paradise retreat to pay for itself!...	4 beds \| 2 baths \| 1,460 sq.ft.	$899,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.61% Airbnb Rental Income: $813 Traditional Rental Income: $3489 Airbnb ROI: -0.97% Traditional ROI: 2.61%
1433 Sunset Road Big Pine Key, FL Great price reduction on income producing CBS duplex in Big Pine Key. Good boating with di...	4 beds \| 3 baths \| 1,924 sq.ft.	$799,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.04% Airbnb Rental Income: $9228 Traditional Rental Income: $4379 Airbnb ROI: 8.24% Traditional ROI: 4.04%
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.	$2,650,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 0.58% Airbnb Rental Income: $9228 Traditional Rental Income: $5379 Airbnb ROI: 1.44% Traditional ROI: 0.58%
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.	$5,800,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.01% Airbnb Rental Income: $null Traditional Rental Income: $5795 Airbnb ROI: N/A Traditional ROI: -0.01%
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: 1.25% Airbnb Rental Income: $8598 Traditional Rental Income: $3957 Airbnb ROI: 3.16% Traditional ROI: 1.25%
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.	$825,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.64% Airbnb Rental Income: $2049 Traditional Rental Income: $2710 Airbnb ROI: 0.09% Traditional ROI: 1.64%
30329 Heron Lane Big Pine Key, FL Nature Lover's Waterfront Retreat on a Rare Double Canal Lot. Imagine living where the sky...	3 beds \| 2 baths \| 1,302 sq.ft.	$1,199,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 1.27% Airbnb Rental Income: $9228 Traditional Rental Income: $3087 Airbnb ROI: 5.23% Traditional ROI: 1.27%

Real Estate investment in Big-pine-key, FL

There are 46 properties for sale in the city of Big Pine Key . The median list price in Big Pine Key is $980,000 and the average price per square foot is $637. In February 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 $2,758.

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

There are 46 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

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: 1.8%

Airbnb Rental Income: $9228

Traditional Rental Income: $2615

Airbnb ROI: 8.48%

Traditional ROI: 1.8%

3746 Park Avenue

Big Pine Key, FL

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

$1,850,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $2049

Traditional Rental Income: $3006

Airbnb ROI: -0.59%

Traditional ROI: 0.28%

29051 Magnolia Ln

Big Pine Key, FL

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

$1,099,000

Airbnb cash on cash: 5.68%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $9228

Traditional Rental Income: $3346

Airbnb ROI: 5.68%

Traditional ROI: 1.62%

1657 Watson Boulevard

Big Pine Key, FL

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

$1,399,000

Airbnb cash on cash: 4.18%

Traditional cash on cash: 0.92%

Airbnb Rental Income: $9228

Traditional Rental Income: $3255

Airbnb ROI: 4.18%

Traditional ROI: 0.92%

31568 AVENUE D

Big Pine Key, FL

3 beds | 2 baths | 1,536 sq.ft.

$727,000

Airbnb cash on cash: 9.64%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $9228

Traditional Rental Income: $3063

Airbnb ROI: 9.64%

Traditional ROI: 3.09%

29523 Enterprise Avenue

Big Pine Key, FL

3 beds | 2 baths | 1,539 sq.ft.

$1,080,000

Airbnb cash on cash: 5.63%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $9228

Traditional Rental Income: $5145

Airbnb ROI: 5.63%

Traditional ROI: 3.29%

30363 Flamingo Lane

Big Pine Key, FL

3 beds | 3 baths | 1,837 sq.ft.

$1,785,000

Airbnb cash on cash: 3.05%

Traditional cash on cash: 0.89%

Airbnb Rental Income: $9228

Traditional Rental Income: $3928

Airbnb ROI: 3.05%

Traditional ROI: 0.89%

1672 Pandorea Lane

Big Pine Key, FL

2 beds | 2 baths | 912 sq.ft.

$799,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2049

Traditional Rental Income: $2716

Airbnb ROI: 0.19%