Airbnb Properties for Sale in Chipley, FL

Looking for a vacation rental investment in Chipley, FL with high ROI ?

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

Airbnb For Sale in Chipley, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3918 Bricknell Avenue Chipley, FL Back on the market! NO FAULT TO SELLER. This 3 bedroom, 2 bathroom brick home offers a com...	3 beds \| 2 baths \| 1,259 sq.ft.	$194,900	Airbnb cash on cash: 8.36% Traditional cash on cash: 6.8% Airbnb Rental Income: $2538 Traditional Rental Income: $1638 Airbnb ROI: 8.36% Traditional ROI: 6.8%
2367 Tiller Road Chipley, FL Enjoy the space and possibilities of country living with this home situated on approximate...	3 beds \| 2 baths \| 1,352 sq.ft.	$299,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 4.56% Airbnb Rental Income: $2538 Traditional Rental Income: $1726 Airbnb ROI: 5.27% Traditional ROI: 4.56%
760 Brown Street Chipley, FL With an acceptable offer, the sellers are offering to pay for a 1-year home warranty and a...	3 beds \| 2 baths \| 1,479 sq.ft.	$184,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 8.24% Airbnb Rental Income: $2538 Traditional Rental Income: $1810 Airbnb ROI: 8.9% Traditional ROI: 8.24%
3955 Highway 77 Chipley, FL This is the space you have been looking for! With over 3,600 square feet heated and cooled...	4 beds \| 3 baths \| 3,625 sq.ft.	$599,999	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.13% Airbnb Rental Income: $4916 Traditional Rental Income: $3218 Airbnb ROI: 5.36% Traditional ROI: 4.13%
3320 Cardinal Place Chipley, FL MOTIVATED SELLERS Welcome home to peaceful country living in the gated Leisure Lakes com...	3 beds \| 2 baths \| 1,714 sq.ft.	$205,000	Airbnb cash on cash: 7.43% Traditional cash on cash: 6.4% Airbnb Rental Income: $2538 Traditional Rental Income: $1726 Airbnb ROI: 7.43% Traditional ROI: 6.4%
1186 Pine Forest Road Chipley, FL PRICE IMPROVEMENT! Tucked away on a beautiful and peaceful 17.5-acre parcel, this charming...	4 beds \| 3 baths \| 2,899 sq.ft.	$489,000	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.5% Airbnb Rental Income: $4916 Traditional Rental Income: $3014 Airbnb ROI: 6.46% Traditional ROI: 4.5%
661 US-90 Chipley, FL Discover the perfect blend of modern comfort and peaceful country living in this beautiful...	4 beds \| 3 baths \| 2,348 sq.ft.	$459,900	Airbnb cash on cash: 7.54% Traditional cash on cash: 4.55% Airbnb Rental Income: $4916 Traditional Rental Income: $2621 Airbnb ROI: 7.54% Traditional ROI: 4.55%
2186 Hague Lane Chipley, FL BRAND NEW CONSTRUCTION in Sunny Hills! This beautifully finished 3-bedroom, 2-bath home of...	3 beds \| 2 baths \| 1,331 sq.ft.	$238,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 6.59% Airbnb Rental Income: $2538 Traditional Rental Income: $1815 Airbnb ROI: 7.09% Traditional ROI: 6.59%
4152 Leisure Lakes Drive Chipley, FL Priced to sell and move-in ready, this spacious home on nearly 3 peaceful acres is an incr...	4 beds \| 3 baths \| 2,916 sq.ft.	$369,900	Airbnb cash on cash: 8.84% Traditional cash on cash: 6.3% Airbnb Rental Income: $4916 Traditional Rental Income: $3026 Airbnb ROI: 8.84% Traditional ROI: 6.3%
1191 Florence Court Chipley, FL Solara Homes is offering a 4.99% 5/1 ARM or 5.50% fixed rate on government loans through C...	3 beds \| 2 baths \| 1,300 sq.ft.	$254,900	Airbnb cash on cash: 6.56% Traditional cash on cash: 6.03% Airbnb Rental Income: $2538 Traditional Rental Income: $1798 Airbnb ROI: 6.56% Traditional ROI: 6.03%
3782 Airmont Drive Chipley, FL * BRAND NEW CUSTOM HOME, BRAND NEW PRICE! * Just reduced by over $15,000!! This stunni...	3 beds \| 2 baths \| 1,424 sq.ft.	$242,500	Airbnb cash on cash: 6.95% Traditional cash on cash: 6.68% Airbnb Rental Income: $2538 Traditional Rental Income: $1864 Airbnb ROI: 6.95% Traditional ROI: 6.68%
550 Bennett Drive Chipley, FL Recently renovated, this 3-bedroom, 2-bath home at 550 Bennett Drive in Chipley features l...	3 beds \| 2 baths \| 1,431 sq.ft.	$159,900	Airbnb cash on cash: 9.47% Traditional cash on cash: 9.16% Airbnb Rental Income: $2538 Traditional Rental Income: $1878 Airbnb ROI: 9.47% Traditional ROI: 9.16%
3370 Peppervine Pl Chipley, FL Privacy, land, and modern comfort meet in this upgraded 2024 Clayton LulaBell nestled on n...	4 beds \| 3 baths \| 2,140 sq.ft.	$385,000	Airbnb cash on cash: 8.76% Traditional cash on cash: 5.86% Airbnb Rental Income: $4916 Traditional Rental Income: $2863 Airbnb ROI: 8.76% Traditional ROI: 5.86%
1990 Ambassador Court Chipley, FL Beautifully designed three-bedroom, two-bath home situated on an oversized homesite in Sun...	3 beds \| 2 baths \| 1,300 sq.ft.	$254,900	Airbnb cash on cash: 6.56% Traditional cash on cash: 5.99% Airbnb Rental Income: $2538 Traditional Rental Income: $1789 Airbnb ROI: 6.56% Traditional ROI: 5.99%

Vacation Rentals in Chipley

There are 14 vacation rental properties available for sale in the city of Chipley . The median list price of Airbnb properties available for sale in Chipley is $189,060 and the average price per square foot is $103. The cash on cash return on vacation rentals in Chipley is 6.00%. The average monthly short term rental income in Chipley is $2,538.

Chipley, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 14 Airbnb properties available for sale in Chipley.

In 2026, the best neighborhood to buy short term rental property is Chipley.

In November 2026, the average Airbnb occupancy rate in Chipley is 39%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chipley, FL

3918 Bricknell Avenue

Chipley, FL

3 beds | 2 baths | 1,259 sq.ft.

$194,900

Airbnb cash on cash: 8.36%

Traditional cash on cash: 6.8%

Airbnb Rental Income: $2538

Traditional Rental Income: $1638

Airbnb ROI: 8.36%

Traditional ROI: 6.8%

2367 Tiller Road

Chipley, FL

3 beds | 2 baths | 1,352 sq.ft.

$299,900

Airbnb cash on cash: 5.27%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $2538

Traditional Rental Income: $1726

Airbnb ROI: 5.27%

Traditional ROI: 4.56%

760 Brown Street

Chipley, FL

3 beds | 2 baths | 1,479 sq.ft.

$184,900

Airbnb cash on cash: 8.9%

Traditional cash on cash: 8.24%

Airbnb Rental Income: $2538

Traditional Rental Income: $1810

Airbnb ROI: 8.9%

Traditional ROI: 8.24%

3955 Highway 77

Chipley, FL

4 beds | 3 baths | 3,625 sq.ft.

$599,999

Airbnb cash on cash: 5.36%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $4916

Traditional Rental Income: $3218

Airbnb ROI: 5.36%

Traditional ROI: 4.13%

3320 Cardinal Place

Chipley, FL

3 beds | 2 baths | 1,714 sq.ft.

$205,000

Airbnb cash on cash: 7.43%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $2538

Traditional Rental Income: $1726

Airbnb ROI: 7.43%

Traditional ROI: 6.4%

1186 Pine Forest Road

Chipley, FL

4 beds | 3 baths | 2,899 sq.ft.

$489,000

Airbnb cash on cash: 6.46%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $4916

Traditional Rental Income: $3014

Airbnb ROI: 6.46%

Traditional ROI: 4.5%

661 US-90

Chipley, FL

4 beds | 3 baths | 2,348 sq.ft.

$459,900

Airbnb cash on cash: 7.54%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4916

Traditional Rental Income: $2621

Airbnb ROI: 7.54%

Traditional ROI: 4.55%

2186 Hague Lane

Chipley, FL

3 beds | 2 baths | 1,331 sq.ft.

$238,000

Airbnb cash on cash: 7.09%

Traditional cash on cash: 6.59%

Airbnb Rental Income: $2538

Traditional Rental Income: $1815

Airbnb ROI: 7.09%