Airbnb Properties for Sale in Big Pine Key, FL

Looking for a vacation rental investment in Big Pine Key, FL with high ROI ?

Explore a range of newly added short-term rental homes in Big Pine Key, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Big Pine Key, FL

Q: How many Airbnb properties are available for sale in Big-pine-key?

There are 36 Airbnb properties available for sale in Big-pine-key

Q: What is the average Airbnb occupancy rate in Big-pine-key, FL?

In September 2026, the average Airbnb occupancy rate in Big-pine-key is 33%.

Q: How to get Big-pine-key, FL Airbnb data?

Airbnb data on vacation rentals in Big-pine-key, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Big-pine-key, FL market insights, guest information and booking details, seasonality trends and historical Big-pine-key, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
29284 Coconut Palm Drive Big Pine Key, FL Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush...	2 beds \| 1 baths \| 812 sq.ft.	$520,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.51% Airbnb Rental Income: $4377 Traditional Rental Income: $3141 Airbnb ROI: 5.16% Traditional ROI: 4.51%
31011 Avenue C Big Pine Key, FL This 4-bedroom, 2-bath, 1566 sq. ft. home has so much to offer for the price! A spacious l...	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%
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.	$1,199,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 1.48% Airbnb Rental Income: $9228 Traditional Rental Income: $3604 Airbnb ROI: 4.97% Traditional ROI: 1.48%
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.	$1,199,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 2.19% Airbnb Rental Income: $9228 Traditional Rental Income: $4316 Airbnb ROI: 5.04% Traditional ROI: 2.19%
30995 Watson Boulevard Big Pine Key, FL Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level re...	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%
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.	$2,069,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.28% Airbnb Rental Income: $9228 Traditional Rental Income: $5396 Airbnb ROI: 2.37% Traditional ROI: 1.28%
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.	$1,150,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 5.02% Airbnb Rental Income: $9228 Traditional Rental Income: $7247 Airbnb ROI: 5.26% Traditional ROI: 5.02%
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.	$549,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 1.64% Airbnb Rental Income: $4377 Traditional Rental Income: $1783 Airbnb ROI: 4.9% Traditional ROI: 1.64%
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.	$964,999	Airbnb cash on cash: 6.59% Traditional cash on cash: 2.94% Airbnb Rental Income: $9228 Traditional Rental Income: $4223 Airbnb ROI: 6.59% Traditional ROI: 2.94%
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%
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.	$4,650,000	Airbnb cash on cash: 0.07% Traditional cash on cash: -0.25% Airbnb Rental Income: $9228 Traditional Rental Income: $6139 Airbnb ROI: 0.07% Traditional ROI: -0.25%
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%
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 \| 1,224 sq.ft.	$727,000	Airbnb cash on cash: 9.66% Traditional cash on cash: 4.59% Airbnb Rental Income: $9228 Traditional Rental Income: $4061 Airbnb ROI: 9.66% Traditional ROI: 4.59%
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 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%
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.	$975,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 1.33% Airbnb Rental Income: $4377 Traditional Rental Income: $2496 Airbnb ROI: 2.39% Traditional ROI: 1.33%
29555 Enterprise Avenue Big Pine Key, FL Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal livi...	3 beds \| 2 baths \| 1,352 sq.ft.	$1,045,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 1.47% Airbnb Rental Income: $9228 Traditional Rental Income: $3207 Airbnb ROI: 5.89% Traditional ROI: 1.47%
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.	$1,125,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 0.98% Airbnb Rental Income: $8598 Traditional Rental Income: $2877 Airbnb ROI: 4.9% Traditional ROI: 0.98%
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.	$899,000	Airbnb cash on cash: 7.65% Traditional cash on cash: 2.69% Airbnb Rental Income: $9228 Traditional Rental Income: $3346 Airbnb ROI: 7.65% Traditional ROI: 2.69%

Vacation Rentals in Big Pine Key

There are 36 vacation rental properties available for sale in the city of Big Pine Key . The median list price of Airbnb properties available for sale in Big Pine Key is $789,528 and the average price per square foot is $512. The cash on cash return on vacation rentals in Big Pine Key is 2.00%. The average monthly short term rental income in Big Pine Key is $8,598.

Big Pine Key, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 36 Airbnb properties available for sale in Big Pine Key.

In 2026, the best neighborhood to buy short term rental property is Big Pine Key.

In September 2026, the average Airbnb occupancy rate in Big Pine Key is 33%.

Airbnb data on vacation rentals in Big Pine Key, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Big Pine Key, FL market insights, guest information and booking details, seasonality trends and historical Big Pine Key, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Big Pine Key, FL

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%

29284 Coconut Palm Drive

Big Pine Key, FL

2 beds | 1 baths | 812 sq.ft.

$520,000

Airbnb cash on cash: 5.16%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $4377

Traditional Rental Income: $3141

Airbnb ROI: 5.16%

Traditional ROI: 4.51%

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%

1632 Bogie Drive

Big Pine Key, FL

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

$1,199,000

Airbnb cash on cash: 4.97%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $9228

Traditional Rental Income: $3604

Airbnb ROI: 4.97%

Traditional ROI: 1.48%

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.

$1,199,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $9228

Traditional Rental Income: $4316

Airbnb ROI: 5.04%

Traditional ROI: 2.19%

30995 Watson Boulevard

Big Pine Key, FL

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%