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
561 Lakepointe Drive Chipley, FL Escape to Your Private Lakepointe Sanctuary Nestled on a full acre in the coveted Lakepoin...	3 beds \| 2 baths \| 1,642 sq.ft.	$364,900	Airbnb cash on cash: 7.66% Traditional cash on cash: 5.21% Airbnb Rental Income: $4189 Traditional Rental Income: $2463 Airbnb ROI: 7.66% Traditional ROI: 5.21%
3034 Paradise Lakes Road Chipley, FL Get your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront ...	3 beds \| 2 baths \| 1,392 sq.ft.	$450,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 4.45% Airbnb Rental Income: $4189 Traditional Rental Income: $2636 Airbnb ROI: 6.03% Traditional ROI: 4.45%
490 Quail Hollow Boulevard Chipley, FL Oasis in the 'Hills! This property has everything you could ever need and is priced below ...	4 beds \| 2 baths \| 2,304 sq.ft.	$440,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 5.86% Airbnb Rental Income: $4916 Traditional Rental Income: $2992 Airbnb ROI: 8.08% Traditional ROI: 5.86%
1730 Firetower Road Chipley, FL Getaway in the country! This 3br/2ba block home has so much to offer: Metal roof, HVAC 202...	3 beds \| 2 baths \| 1,529 sq.ft.	$335,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 5.35% Airbnb Rental Income: $4189 Traditional Rental Income: $2232 Airbnb ROI: 8.75% Traditional ROI: 5.35%
1962 Mud Hill Road Chipley, FL Looking for privacy? This is it! Situated on approximately 40 acres, 1962 Mud Hill Road of...	4 beds \| 2 baths \| 2,297 sq.ft.	$459,900	Airbnb cash on cash: 7.7% Traditional cash on cash: 4.61% Airbnb Rental Income: $4916 Traditional Rental Income: $2581 Airbnb ROI: 7.7% Traditional ROI: 4.61%
2474 Tiller Cemetery Drive Chipley, FL 35 acres, Heated pool, Ponds, abundant wildlife, and room to breathe. This isn't just a pr...	4 beds \| 3 baths \| 1,941 sq.ft.	$599,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 2.42% Airbnb Rental Income: $4916 Traditional Rental Income: $2503 Airbnb ROI: 4.93% Traditional ROI: 2.42%
3955 Hwy. 77 Chipley, FL OW -- what an incredible property! Nearly 20 acres featuring a spacious home designed for ...	4 beds \| 3 baths \| 3,564 sq.ft.	$675,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.57% Airbnb Rental Income: $4916 Traditional Rental Income: $3218 Airbnb ROI: 4.67% Traditional ROI: 3.57%
3980 Quail Court Chipley, FL Completely renovated home with In-law/Guest house! This beautifully styled home has been c...	3 beds \| 3 baths \| 1,810 sq.ft.	$460,000	Airbnb cash on cash: 6% Traditional cash on cash: 3.53% Airbnb Rental Income: $4189 Traditional Rental Income: $2238 Airbnb ROI: 6% Traditional ROI: 3.53%
2121 Angora Drive Chipley, FL Welcome to 2121 Angora Dr! This home sits on almost a half an acre with an inground pool. ...	3 beds \| 2 baths \| 1,642 sq.ft.	$299,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 5.51% Airbnb Rental Income: $4189 Traditional Rental Income: $2076 Airbnb ROI: 9.86% Traditional ROI: 5.51%
1186 Pine Forest Road Chipley, FL Tucked away on a generous 17.5-acre parcel, this charming 2,899 SF, 4-bedroom, 2.5-bath ho...	4 beds \| 3 baths \| 2,899 sq.ft.	$550,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.8% Airbnb Rental Income: $4916 Traditional Rental Income: $3014 Airbnb ROI: 5.54% Traditional ROI: 3.8%
3385 Orange Hill Road Chipley, FL Nestled on 4.83 picturesque acres, this charming 3-bedroom, 2.5-bath home at 3385 Orange H...	3 beds \| 3 baths \| 1,538 sq.ft.	$324,900	Airbnb cash on cash: 9.23% Traditional cash on cash: 4.1% Airbnb Rental Income: $4189 Traditional Rental Income: $1733 Airbnb ROI: 9.23% Traditional ROI: 4.1%
3256 Highway 77 Chipley, FL Located on 48.42 acres, this spacious 3-bedroom, 2-bathroom home offers 2,385 sq ft of com...	3 beds \| 2 baths \| 2,385 sq.ft.	$589,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 2.47% Airbnb Rental Income: $4189 Traditional Rental Income: $2121 Airbnb ROI: 4.61% Traditional ROI: 2.47%
1712 Shamrock Lane Chipley, FL Spacious brick home on acreage in the desirable Orange Hill area, conveniently located jus...	4 beds \| 3 baths \| 2,938 sq.ft.	$449,900	Airbnb cash on cash: 7.66% Traditional cash on cash: 5.42% Airbnb Rental Income: $4916 Traditional Rental Income: $2961 Airbnb ROI: 7.66% Traditional ROI: 5.42%

Vacation Rentals in Chipley

There are 13 vacation rental properties available for sale in the city of Chipley . The median list price of Airbnb properties available for sale in Chipley is $204,894 and the average price per square foot is $122. The cash on cash return on vacation rentals in Chipley is 12.00%. The average monthly short term rental income in Chipley is $4,189.

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

There are 13 Airbnb properties available for sale in Chipley.

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

In June 2026, the average Airbnb occupancy rate in Chipley is 50%.

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

561 Lakepointe Drive

Chipley, FL

3 beds | 2 baths | 1,642 sq.ft.

$364,900

Airbnb cash on cash: 7.66%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $4189

Traditional Rental Income: $2463

Airbnb ROI: 7.66%

Traditional ROI: 5.21%

3034 Paradise Lakes Road

Chipley, FL

3 beds | 2 baths | 1,392 sq.ft.

$450,000

Airbnb cash on cash: 6.03%

Traditional cash on cash: 4.45%

Airbnb Rental Income: $4189

Traditional Rental Income: $2636

Airbnb ROI: 6.03%

Traditional ROI: 4.45%

490 Quail Hollow Boulevard

Chipley, FL

4 beds | 2 baths | 2,304 sq.ft.

$440,000

Airbnb cash on cash: 8.08%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $4916

Traditional Rental Income: $2992

Airbnb ROI: 8.08%

Traditional ROI: 5.86%

1730 Firetower Road

Chipley, FL

3 beds | 2 baths | 1,529 sq.ft.

$335,000

Airbnb cash on cash: 8.75%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $4189

Traditional Rental Income: $2232

Airbnb ROI: 8.75%

Traditional ROI: 5.35%

1962 Mud Hill Road

Chipley, FL

4 beds | 2 baths | 2,297 sq.ft.

$459,900

Airbnb cash on cash: 7.7%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $4916

Traditional Rental Income: $2581

Airbnb ROI: 7.7%

Traditional ROI: 4.61%

2474 Tiller Cemetery Drive

Chipley, FL

4 beds | 3 baths | 1,941 sq.ft.

$599,900

Airbnb cash on cash: 4.93%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $4916

Traditional Rental Income: $2503

Airbnb ROI: 4.93%

Traditional ROI: 2.42%

3955 Hwy. 77

Chipley, FL

4 beds | 3 baths | 3,564 sq.ft.

$675,000

Airbnb cash on cash: 4.67%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $4916

Traditional Rental Income: $3218

Airbnb ROI: 4.67%

Traditional ROI: 3.57%

3980 Quail Court

Chipley, FL

3 beds | 3 baths | 1,810 sq.ft.

$460,000

Airbnb cash on cash: 6%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $4189

Traditional Rental Income: $2238

Airbnb ROI: 6%