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 42 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
29030 Iris Drive Big Pine Key, FL This 3BR spacious canal front home with quick open water access is nestled at the end of a...	3 beds \| 2 baths \| 1,353 sq.ft.	$719,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 3.37% Airbnb Rental Income: $6776 Traditional Rental Income: $3326 Airbnb ROI: 6.55% Traditional ROI: 3.37%
29457 Constitution Avenue Big Pine Key, FL Solid, Spacious & Ready for Your Island Lifestyle! This 3 BD/3 BA concrete block home is j...	3 beds \| 3 baths \| 1,608 sq.ft.	$1,319,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 1.37% Airbnb Rental Income: $6776 Traditional Rental Income: $3728 Airbnb ROI: 2.78% Traditional ROI: 1.37%
1541 Sunrise Drive Big Pine Key, FL Enjoy absolutely stunning open water views and spectacular sunrises every morning from thi...	3 beds \| 2 baths \| 2,068 sq.ft.	$1,399,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 1.29% Airbnb Rental Income: $6776 Traditional Rental Income: $3765 Airbnb ROI: 2.6% Traditional ROI: 1.29%
651 Pine Lane Big Pine Key, FL Nestled in the heart of Big Pine Key, this fantastic property offers 4 bedrooms, 2 baths, ...	4 beds \| 2 baths \| 2,176 sq.ft.	$1,245,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 1.77% Airbnb Rental Income: $8598 Traditional Rental Income: $4030 Airbnb ROI: 4.31% Traditional ROI: 1.77%
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: 0.8% Traditional cash on cash: 0.28% Airbnb Rental Income: $4913 Traditional Rental Income: $3006 Airbnb ROI: 0.8% Traditional ROI: 0.28%
1659 LONG BEACH DRIVE Big Pine Key, FL Motivated Seller, Let's make a deal! One of the ONLY luxury Oceanfront homes with your own...	3 beds \| 2 baths \| 1,850 sq.ft.	$2,199,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.52% Airbnb Rental Income: $6776 Traditional Rental Income: $3852 Airbnb ROI: 1.3% Traditional ROI: 0.52%
29051 MAGNOLIA LANE Big Pine Key, FL Welcome to 29051 Magnolia Lane in Big Pine Key, FL! This inviting home offers a 2-bedroom,...	3 beds \| 3 baths \| 1,344 sq.ft.	$1,165,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 1.47% Airbnb Rental Income: $6776 Traditional Rental Income: $3346 Airbnb ROI: 3.42% Traditional ROI: 1.47%
31243 E Avenue Big Pine Key, FL *Price Improvement Welcome to your slice of paradise in Big Pine Key! This charming 3-b...	3 beds \| 2 baths \| 1,204 sq.ft.	$639,900	Airbnb cash on cash: 7.21% Traditional cash on cash: 2.26% Airbnb Rental Income: $6776 Traditional Rental Income: $2498 Airbnb ROI: 7.21% Traditional ROI: 2.26%
30461 Poinciana Rd Big Pine Key, FL Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 b...	3 beds \| 2 baths \| 1,431 sq.ft.	$565,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 4.4% Airbnb Rental Income: $6776 Traditional Rental Income: $3413 Airbnb ROI: 8.27% Traditional ROI: 4.4%
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: 6.62% Traditional cash on cash: 3.09% Airbnb Rental Income: $6776 Traditional Rental Income: $3063 Airbnb ROI: 6.62% Traditional ROI: 3.09%
117 W Sandy Circle Big Pine Key, FL Looking for that Family Home in The Florida Keys that fits your budget, well you just foun...	4 beds \| 2 baths \| 1,200 sq.ft.	$625,000	Airbnb cash on cash: 9.95% Traditional cash on cash: 2.86% Airbnb Rental Income: $8598 Traditional Rental Income: $2839 Airbnb ROI: 9.95% Traditional ROI: 2.86%
1672 Pandorea Ln Big Pine Key, FL Clean corner-lot stilted canal-front home on Big Pine! 2/2 up. Recently updated. New centr...	3 beds \| 3 baths \| 912 sq.ft.	$799,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 1.81% Airbnb Rental Income: $6776 Traditional Rental Income: $2716 Airbnb ROI: 5.5% Traditional ROI: 1.81%
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%
1633 Lantana Lane Big Pine Key, FL Located in Big Pine Key, this 3-bedroom, 2-bathroom, canal front Pool Home is a perfect bl...	3 beds \| 2 baths \| 1,204 sq.ft.	$949,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 1.39% Airbnb Rental Income: $6776 Traditional Rental Income: $2829 Airbnb ROI: 4.36% Traditional ROI: 1.39%
550 Pine Lane Big Pine Key, FL This newly remodeled 2-bedroom, 1-bathroom home is perfectly positioned on two spacious lo...	3 beds \| 1 baths \| 1,043 sq.ft.	$1,275,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 0.61% Airbnb Rental Income: $6776 Traditional Rental Income: $2522 Airbnb ROI: 3.09% Traditional ROI: 0.61%
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: 4.23% Traditional cash on cash: 4.78% Airbnb Rental Income: $6776 Traditional Rental Income: $5960 Airbnb ROI: 4.23% 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.	$1,249,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.74% Airbnb Rental Income: $6776 Traditional Rental Income: $5066 Airbnb ROI: 3.08% Traditional ROI: 2.74%
3 W Cook Big Pine Key, FL Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfron...	3 beds \| 2 baths \| 704 sq.ft.	$549,000	Airbnb cash on cash: 9.36% Traditional cash on cash: 3.16% Airbnb Rental Income: $6776 Traditional Rental Income: $2277 Airbnb ROI: 9.36% Traditional ROI: 3.16%
29487 Ranger Avenue Big Pine Key, FL Waterfront Living in Big Pine Key! Well-Built Canal Home in Prime Lower Keys Location: T...	2 beds \| 2 baths \| 1,258 sq.ft.	$979,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 1.38% Airbnb Rental Income: $4913 Traditional Rental Income: $2888 Airbnb ROI: 2.49% Traditional ROI: 1.38%
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.	$1,999,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 1.12% Airbnb Rental Income: $6776 Traditional Rental Income: $5044 Airbnb ROI: 1.34% Traditional ROI: 1.12%
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.	$1,150,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.58% Airbnb Rental Income: $4913 Traditional Rental Income: $3146 Airbnb ROI: 2.29% Traditional ROI: 1.58%
30342 Hibiscus Lane Big Pine Key, FL Look no further.....this charming Big Pine Key Cottage has all the comforts you are lookin...	3 beds \| 2 baths \| 1,508 sq.ft.	$565,000	Airbnb cash on cash: 8.36% Traditional cash on cash: 4.21% Airbnb Rental Income: $6776 Traditional Rental Income: $3268 Airbnb ROI: 8.36% Traditional ROI: 4.21%
29676 Ranger Avenue Big Pine Key, FL This expansive, 15,500 sq. ft. double lot in desirable Pine Channel Estates offers privacy...	2 beds \| 2 baths \| 1,064 sq.ft.	$1,250,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 1.61% Airbnb Rental Income: $4913 Traditional Rental Income: $3346 Airbnb ROI: 2.1% Traditional ROI: 1.61%
31516 Avenue F Big Pine Key, FL Experience the ultimate Florida Keys lifestyle in this beautiful brand new waterfront home...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,394,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 1% Airbnb Rental Income: $6776 Traditional Rental Income: $3303 Airbnb ROI: 2.66% Traditional ROI: 1%
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.	$799,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 2% Airbnb Rental Income: $6776 Traditional Rental Income: $2588 Airbnb ROI: 5.86% Traditional ROI: 2%
29176 Violet Drive Big Pine Key, FL Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen p...	5 beds \| 4 baths \| 2,447 sq.ft.	$2,340,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.37% Airbnb Rental Income: $null Traditional Rental Income: $5940 Airbnb ROI: N/A Traditional ROI: 1.37%
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.	$1,399,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.64% Airbnb Rental Income: $4913 Traditional Rental Income: $2580 Airbnb ROI: 1.66% Traditional ROI: 0.64%
29115 Rose Drive Big Pine Key, FL Welcome to this meticulously maintained, move-in ready canal-front home that offers the pe...	3 beds \| 2 baths \| 1,250 sq.ft.	$837,500	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.43% Airbnb Rental Income: $6776 Traditional Rental Income: $2943 Airbnb ROI: 5.66% Traditional ROI: 2.43%
3714 Pine Street Big Pine Key, FL Welcome to your dream waterfront retreat! This 1,120 sq. ft. 2-bedroom, 2-bath home offers...	2 beds \| 2 baths \| 1,120 sq.ft.	$829,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 1.7% Airbnb Rental Income: $4913 Traditional Rental Income: $2694 Airbnb ROI: 3.27% Traditional ROI: 1.7%
32734 Bimini Lane Big Pine Key, FL Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a s...	3 beds \| 2 baths \| 1,654 sq.ft.	$1,225,000	Airbnb cash on cash: 3% Traditional cash on cash: 1.32% Airbnb Rental Income: $6776 Traditional Rental Income: $3542 Airbnb ROI: 3% Traditional ROI: 1.32%
10 W Cook Big Pine Key, FL Welcome to Cook Island, a semi-private pristine barrier island offering one of the most be...	3 beds \| 1 baths \| 1,162 sq.ft.	$699,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 2.57% Airbnb Rental Income: $6776 Traditional Rental Income: $2854 Airbnb ROI: 6.57% Traditional ROI: 2.57%
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.	$1,250,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 1.07% Airbnb Rental Income: $4913 Traditional Rental Income: $3032 Airbnb ROI: 1.82% Traditional ROI: 1.07%
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%
31131 Ave D Big Pine Key, FL Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Be...	2 beds \| 1 baths \| 754 sq.ft.	$459,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 2.86% Airbnb Rental Income: $4913 Traditional Rental Income: $2081 Airbnb ROI: 7.11% Traditional ROI: 2.86%
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.	$6,450,000	Airbnb cash on cash: -0.53% Traditional cash on cash: -0.8% Airbnb Rental Income: $6776 Traditional Rental Income: $3839 Airbnb ROI: -0.53% Traditional ROI: -0.8%
1341 Avenue C Big Pine Key, FL Welcome to 1341 Avenue C, Big Pine Key - Your Peaceful Island RetreatTucked away in the he...	3 beds \| 2 baths \| 1,452 sq.ft.	$699,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 2.95% Airbnb Rental Income: $6776 Traditional Rental Income: $3111 Airbnb ROI: 6.55% Traditional ROI: 2.95%
30319 Falcon Lane Big Pine Key, FL Surrounded by the natural beauty of the Florida Keys, this canal front home blends privacy...	2 beds \| 3 baths \| 1,840 sq.ft.	$1,147,300	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.79% Airbnb Rental Income: $4913 Traditional Rental Income: $3805 Airbnb ROI: 1.89% Traditional ROI: 1.79%
29283 Coconut Palm Drive Big Pine Key, FL Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residentia...	3 beds \| 2 baths \| 1,247 sq.ft.	$739,000	Airbnb cash on cash: 6.65% Traditional cash on cash: 2.69% Airbnb Rental Income: $6776 Traditional Rental Income: $2734 Airbnb ROI: 6.65% Traditional ROI: 2.69%

Your search for investment property begins and ends here

Single Family Homes for Sale in Big Pine Key, FL

29030 Iris Drive

Big Pine Key, FL

3 beds | 2 baths | 1,353 sq.ft.

$719,000

Airbnb cash on cash: 6.55%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $6776

Traditional Rental Income: $3326

Airbnb ROI: 6.55%

Traditional ROI: 3.37%

29457 Constitution Avenue

Big Pine Key, FL

3 beds | 3 baths | 1,608 sq.ft.

$1,319,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $6776

Traditional Rental Income: $3728

Airbnb ROI: 2.78%

Traditional ROI: 1.37%

1541 Sunrise Drive

Big Pine Key, FL

3 beds | 2 baths | 2,068 sq.ft.

$1,399,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $6776

Traditional Rental Income: $3765

Airbnb ROI: 2.6%

Traditional ROI: 1.29%

651 Pine Lane

Big Pine Key, FL

4 beds | 2 baths | 2,176 sq.ft.

$1,245,000

Airbnb cash on cash: 4.31%

Traditional cash on cash: 1.77%

Airbnb Rental Income: $8598

Traditional Rental Income: $4030

Airbnb ROI: 4.31%

Traditional ROI: 1.77%

3746 Park Avenue

Big Pine Key, FL

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

$1,850,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $4913

Traditional Rental Income: $3006

Airbnb ROI: 0.8%

Traditional ROI: 0.28%

1659 LONG BEACH DRIVE

Big Pine Key, FL

3 beds | 2 baths | 1,850 sq.ft.

$2,199,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $6776

Traditional Rental Income: $3852

Airbnb ROI: 1.3%

Traditional ROI: 0.52%

29051 MAGNOLIA LANE

Big Pine Key, FL

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

$1,165,000

Airbnb cash on cash: 3.42%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $6776

Traditional Rental Income: $3346

Airbnb ROI: 3.42%

Traditional ROI: 1.47%

31243 E Avenue

Big Pine Key, FL

3 beds | 2 baths | 1,204 sq.ft.

$639,900

Airbnb cash on cash: 7.21%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $6776

Traditional Rental Income: $2498

Airbnb ROI: 7.21%