Real Estate Investment Properties for Sale in Key West, FL

Looking for investment property in Key West, FL with high ROI ?

Explore a variety of short-term homes & houses in Key West, FL. Invest wisely with VRBO & Key West, 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 Key West, FL

Search for Single Family Residential for Sale in Key West, 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 103 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
1119 Whitehead Street Key West, FL This stunning Old Town residence offers the perfect blend of historic charm and modern ele...	3 beds \| 2 baths \| 1,665 sq.ft.	$2,499,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 0.16% Airbnb Rental Income: $11712 Traditional Rental Income: $3920 Airbnb ROI: 2.6% Traditional ROI: 0.16%
702 Florida Street Key West, FL BRAND NEW ROOF with new Kitchen Skylights! This beautiful single-story CBS home is on a de...	2 beds \| 2 baths \| 1,458 sq.ft.	$1,290,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.17% Airbnb Rental Income: $3477 Traditional Rental Income: $3464 Airbnb ROI: 0.54% Traditional ROI: 1.17%
1211 Catherine Street Key West, FL This charming historic home is located just steps off vibrant White St and close to the be...	3 beds \| 2 baths \| 1,463 sq.ft.	$1,680,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 0.71% Airbnb Rental Income: $10831 Traditional Rental Income: $3756 Airbnb ROI: 3.97% Traditional ROI: 0.71%
1420 White Street Key West, FL Stunning Grand Key West Historic Home Newly Renovated into a Gorgeous Single Family Home w...	5 beds \| 3 baths \| 2,608 sq.ft.	$3,299,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 0.26% Airbnb Rental Income: $16799 Traditional Rental Income: $5300 Airbnb ROI: 3.05% Traditional ROI: 0.26%
816 Ashe Street Key West, FL NEW PRICE!! This beautifully renovated conch home is a proud recipient of the 2024 Histori...	3 beds \| 4 baths \| 1,522 sq.ft.	$2,150,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.04% Airbnb Rental Income: $2455 Traditional Rental Income: $4651 Airbnb ROI: -0.36% Traditional ROI: 1.04%
1320 Eliza Street Key West, FL Welcome to the School House on Eliza!1320 Eliza Street is a stunning corner-lot property t...	4 beds \| 4 baths \| 1,854 sq.ft.	$2,599,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 0.72% Airbnb Rental Income: $10782 Traditional Rental Income: $5196 Airbnb ROI: 2.21% Traditional ROI: 0.72%
1104 South Street Key West, FL ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina distri...	3 beds \| 4 baths \| 2,110 sq.ft.	$2,100,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.67% Airbnb Rental Income: $11580 Traditional Rental Income: $5132 Airbnb ROI: 2.89% Traditional ROI: 0.67%
1124 Seminary Street Key West, FL Beautiful home in the Casa Marina District. Completely remodeled in 2020 and the guest cot...	3 beds \| 4 baths \| 1,970 sq.ft.	$2,650,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 0.57% Airbnb Rental Income: $10831 Traditional Rental Income: $5393 Airbnb ROI: 1.97% Traditional ROI: 0.57%
729 Windsor Lane Key West, FL Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rar...	2 beds \| 1 baths \| 723 sq.ft.	$1,175,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 0.37% Airbnb Rental Income: $8333 Traditional Rental Income: $2543 Airbnb ROI: 4.22% Traditional ROI: 0.37%
247 Golf Club Drive Key West, FL Tucked inside the private gates of The Sanctuary at the Key West Golf Club, 247 Golf Club ...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,325,000	Airbnb cash on cash: 5.11% Traditional cash on cash: 0.92% Airbnb Rental Income: $11088 Traditional Rental Income: $3894 Airbnb ROI: 5.11% Traditional ROI: 0.92%
5603 College Road #UNIT D104 Key West, FL Enjoy one of the best priced waterfront properties in Key West. This stunning home is mov...	2 beds \| 2 baths \| 1,171 sq.ft.	$1,049,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 0.17% Airbnb Rental Income: $7456 Traditional Rental Income: $2835 Airbnb ROI: 3.44% Traditional ROI: 0.17%
1001 ed Street #UNIT B Key West, FL Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully re...	3 beds \| 5 baths \| 1,442 sq.ft.	$1,700,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 1.47% Airbnb Rental Income: $11580 Traditional Rental Income: $5193 Airbnb ROI: 4.17% Traditional ROI: 1.47%
243 Golf Club Drive Key West, FL MOTIVATED SELLERS Turn-key home with a history of rentals and a long term lease in place a...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,330,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 0.99% Airbnb Rental Income: $11088 Traditional Rental Income: $3914 Airbnb ROI: 5.15% Traditional ROI: 0.99%
612 Mickens Lane Key West, FL Only 139 steps from the iconic Green Parrot (yes, we counted) and just 1.5 blocks off Duva...	2 beds \| 2 baths \| 823 sq.ft.	$1,195,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 0.39% Airbnb Rental Income: $8036 Traditional Rental Income: $2283 Airbnb ROI: 4.19% Traditional ROI: 0.39%
915 Washington Street Key West, FL Located in the highly sought-after Casa Marina neighborhood, 915 Washington Street offers ...	2 beds \| 2 baths \| 1,193 sq.ft.	$1,795,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 0.38% Airbnb Rental Income: $9249 Traditional Rental Income: $3305 Airbnb ROI: 2.91% Traditional ROI: 0.38%
1701 Atlantic Boulevard Key West, FL A stunning new renovation transforms this spacious elevated home to a total of 5bd/4ba plu...	5 beds \| 4 baths \| 2,703 sq.ft.	$2,599,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.19% Airbnb Rental Income: $null Traditional Rental Income: $6447 Airbnb ROI: N/A Traditional ROI: 1.19%
908 Catherine Street Key West, FL Motivated seller -- Quick Close! Welcome to 908 Catherine Street - a delightful blend of h...	3 beds \| 4 baths \| 1,572 sq.ft.	$1,799,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 2.67% Airbnb Rental Income: $11580 Traditional Rental Income: $6971 Airbnb ROI: 4.16% Traditional ROI: 2.67%
208 Golf Club Drive Key West, FL Welcome to Splendor @ Key West Golf Club, an impeccably transformed courtyard spa home loc...	2 beds \| 3 baths \| 1,120 sq.ft.	$995,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 1.11% Airbnb Rental Income: $7456 Traditional Rental Income: $3273 Airbnb ROI: 4.08% Traditional ROI: 1.11%
1211 Knowles Lane Key West, FL Discover the timeless charm of this beautifully remodeled historic home located in Old Tow...	3 beds \| 3 baths \| 1,284 sq.ft.	$1,595,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 1.12% Airbnb Rental Income: $11580 Traditional Rental Income: $3799 Airbnb ROI: 4.94% Traditional ROI: 1.12%
26 Spoonbill Way Key West, FL Nestled within the prestigious Key West Golf Club, a rare opportunity beckons with this ex...	3 beds \| 2 baths \| 1,350 sq.ft.	$1,145,000	Airbnb cash on cash: 6.63% Traditional cash on cash: 0.42% Airbnb Rental Income: $11088 Traditional Rental Income: $2431 Airbnb ROI: 6.63% Traditional ROI: 0.42%
1705 Von Phister Street Key West, FL Welcome to one of Key West's most inviting neighborhoods, where tree-lined streets and a t...	3 beds \| 3 baths \| 1,284 sq.ft.	$1,245,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.21% Airbnb Rental Income: $2385 Traditional Rental Income: $3432 Airbnb ROI: -0.21% Traditional ROI: 1.21%
202 Admirals Lane Key West, FL Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after...	5 beds \| 4 baths \| 3,148 sq.ft.	$4,850,000	Airbnb cash on cash: 0.43% Traditional cash on cash: -0.58% Airbnb Rental Income: $11896 Traditional Rental Income: $5160 Airbnb ROI: 0.43% Traditional ROI: -0.58%
3365 Flagler Avenue Key West, FL Welcome to 3365 Flagler Avenue, a beautifully updated and meticulously maintained 2 bed, 2...	2 beds \| 2 baths \| 1,339 sq.ft.	$860,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 2.29% Airbnb Rental Income: $7456 Traditional Rental Income: $3220 Airbnb ROI: 5.79% Traditional ROI: 2.29%
3409 Eagle Avenue Key West, FL Introducing 3409 Eagle Avenue, a stunning new home, currently under construction in Key We...	4 beds \| 4 baths \| 2,410 sq.ft.	$2,649,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 0.7% Airbnb Rental Income: $9315 Traditional Rental Income: $5155 Airbnb ROI: 1.69% Traditional ROI: 0.7%
1525 Von Phister Street Key West, FL Elevated, fully renovated and perfectly located on one of Key West's most idyllic streets,...	3 beds \| 2 baths \| 1,434 sq.ft.	$1,899,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.46% Airbnb Rental Income: $2385 Traditional Rental Income: $3793 Airbnb ROI: -0.67% Traditional ROI: 0.46%
2827 Harris Avenue Key West, FL This absolutely stunning 5-bedroom, 5-bathroom home, re-imagined and built brand new in 20...	5 beds \| 5 baths \| 3,086 sq.ft.	$1,949,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $6647 Airbnb ROI: N/A Traditional ROI: 2.15%
90 Golf Club Drive Key West, FL This charming Poolside Key West Golf Club home is ready for you to make your very own vaca...	2 beds \| 3 baths \| 930 sq.ft.	$784,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 2.3% Airbnb Rental Income: $7456 Traditional Rental Income: $3109 Airbnb ROI: 6.29% Traditional ROI: 2.3%
626 Margaret Street Key West, FL Welcome to this captivating historic Conch home, where the essence of Key West island luxu...	3 beds \| 2 baths \| 1,392 sq.ft.	$1,649,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 0.54% Airbnb Rental Income: $11712 Traditional Rental Income: $3626 Airbnb ROI: 4.42% Traditional ROI: 0.54%
312 Margaret Street Key West, FL Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful ho...	3 beds \| 3 baths \| 1,916 sq.ft.	$2,599,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 0.1% Airbnb Rental Income: $12364 Traditional Rental Income: $4621 Airbnb ROI: 2.38% Traditional ROI: 0.1%
817 Terry Lane Key West, FL Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cott...	1 beds \| 1 baths \| 420 sq.ft.	$1,100,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 0.19% Airbnb Rental Income: $6911 Traditional Rental Income: $1858 Airbnb ROI: 3.82% Traditional ROI: 0.19%
3741 Eagle Avenue Key West, FL Experience refined island living in this BRAND NEW residence perfectly situated on a gener...	3 beds \| 4 baths \| 2,744 sq.ft.	$4,130,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 0.37% Airbnb Rental Income: $11088 Traditional Rental Income: $5901 Airbnb ROI: 1.19% Traditional ROI: 0.37%
1022 Fleming Street Key West, FL Invest in Key West with this Duplex which can be also easily used as a single family home!...	4 beds \| 2 baths \| 2,016 sq.ft.	$1,999,990	Airbnb cash on cash: 2.81% Traditional cash on cash: 0.33% Airbnb Rental Income: $10441 Traditional Rental Income: $3909 Airbnb ROI: 2.81% Traditional ROI: 0.33%
1610 Von Phister Street Key West, FL Fully renovated and redefined mid-century home, perfectly tailored for modern island livin...	4 beds \| 4 baths \| 3,656 sq.ft.	$2,925,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.45% Airbnb Rental Income: $2566 Traditional Rental Income: $5293 Airbnb ROI: -0.78% Traditional ROI: 0.45%
1109 Stump Lane Key West, FL Nestled on a tranquil lane in Old Town Key West, this classic Conch home is designed for r...	3 beds \| 4 baths \| 1,724 sq.ft.	$2,400,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 0.39% Airbnb Rental Income: $11712 Traditional Rental Income: $4909 Airbnb ROI: 2.48% Traditional ROI: 0.39%
2911 Seidenberg Avenue Key West, FL Welcome to your dream home in the heart of Key West's MidTown!This beautifully updated 3-...	3 beds \| 2 baths \| 1,052 sq.ft.	$1,195,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 1.2% Airbnb Rental Income: $11088 Traditional Rental Income: $3215 Airbnb ROI: 6.45% Traditional ROI: 1.2%
411 Louisa Street Key West, FL Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located...	5 beds \| 5 baths \| 3,663 sq.ft.	$6,750,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.11% Airbnb Rental Income: $11896 Traditional Rental Income: $9026 Airbnb ROI: 0.22% Traditional ROI: 0.11%
827 Eisenhower Drive Key West, FL Waterfront Old Town Oasis.This exceptional Key West residence is a rare offering in the H...	3 beds \| 3 baths \| 2,397 sq.ft.	$2,300,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.41% Airbnb Rental Income: $2455 Traditional Rental Income: $5458 Airbnb ROI: -1.28% Traditional ROI: 0.41%
103 Front Street Key West, FL 103 Front Street is a one of a kind masterpiece of architectural design and modern aesthet...	3 beds \| 3 baths \| 4,200 sq.ft.	$6,850,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -1.35% Airbnb Rental Income: $12364 Traditional Rental Income: $4788 Airbnb ROI: -0.51% Traditional ROI: -1.35%
2109 Seidenberg Avenue Key West, FL Tropical charm, flexible living, and a fantastic location--welcome to 2109 Seidenberg Aven...	4 beds \| 3 baths \| 1,554 sq.ft.	$1,250,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.87% Airbnb Rental Income: $2566 Traditional Rental Income: $4121 Airbnb ROI: 0% Traditional ROI: 1.87%
711 Galveston Lane Key West, FL Nestled down a private and picturesque lane, this charming conch-style cottage offers the ...	3 beds \| 2 baths \| 866 sq.ft.	$1,250,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 0.89% Airbnb Rental Income: $11712 Traditional Rental Income: $3072 Airbnb ROI: 6.48% Traditional ROI: 0.89%

Your search for investment property begins and ends here

Single Family Homes for Sale in Key West, FL

1119 Whitehead Street

Key West, FL

3 beds | 2 baths | 1,665 sq.ft.

$2,499,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $11712

Traditional Rental Income: $3920

Airbnb ROI: 2.6%

Traditional ROI: 0.16%

702 Florida Street

Key West, FL

2 beds | 2 baths | 1,458 sq.ft.

$1,290,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $3477

Traditional Rental Income: $3464

Airbnb ROI: 0.54%

Traditional ROI: 1.17%

1211 Catherine Street

Key West, FL

3 beds | 2 baths | 1,463 sq.ft.

$1,680,000

Airbnb cash on cash: 3.97%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $10831

Traditional Rental Income: $3756

Airbnb ROI: 3.97%

Traditional ROI: 0.71%

1420 White Street

Key West, FL

5 beds | 3 baths | 2,608 sq.ft.

$3,299,000

Airbnb cash on cash: 3.05%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $16799

Traditional Rental Income: $5300

Airbnb ROI: 3.05%

Traditional ROI: 0.26%

816 Ashe Street

Key West, FL

3 beds | 4 baths | 1,522 sq.ft.

$2,150,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $2455

Traditional Rental Income: $4651

Airbnb ROI: -0.36%

Traditional ROI: 1.04%

1320 Eliza Street

Key West, FL

4 beds | 4 baths | 1,854 sq.ft.

$2,599,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $10782

Traditional Rental Income: $5196

Airbnb ROI: 2.21%

Traditional ROI: 0.72%

1104 South Street

Key West, FL

3 beds | 4 baths | 2,110 sq.ft.

$2,100,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $11580

Traditional Rental Income: $5132

Airbnb ROI: 2.89%

Traditional ROI: 0.67%

1124 Seminary Street

Key West, FL

3 beds | 4 baths | 1,970 sq.ft.

$2,650,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $10831

Traditional Rental Income: $5393

Airbnb ROI: 1.97%