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 82 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
1607 Sunshine Drive Key West, FL Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This n...	3 beds \| 3 baths \| 1,672 sq.ft.	$1,969,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 1.45% Airbnb Rental Income: $11827 Traditional Rental Income: $5163 Airbnb ROI: 3.91% Traditional ROI: 1.45%
1115 Fleming Street Key West, FL This rare Key West treasure hasn't changed hands in over a century, and it sits on the mos...	4 beds \| 2 baths \| 1,760 sq.ft.	$1,875,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.62% Airbnb Rental Income: $7690 Traditional Rental Income: $5932 Airbnb ROI: 1.78% Traditional ROI: 1.62%
1500 5th Street Key West, FL When value matters, this solid concrete New Town home stands apart with one of the most co...	4 beds \| 2 baths \| 2,111 sq.ft.	$979,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.56% Airbnb Rental Income: $5911 Traditional Rental Income: $4419 Airbnb ROI: 3.9% Traditional ROI: 3.56%
1105 Olivia Street Key West, FL This elegant historic Old Town cottage is a rare offering paired with a highly competitive...	1 beds \| 1 baths \| 622 sq.ft.	$819,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 1.04% Airbnb Rental Income: $5797 Traditional Rental Income: $1985 Airbnb ROI: 4.21% Traditional ROI: 1.04%
817 Terry Lane Key West, FL One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of...	1 beds \| 1 baths \| 420 sq.ft.	$935,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 2% Airbnb Rental Income: $5429 Traditional Rental Income: $3425 Airbnb ROI: 2.98% Traditional ROI: 2%
611 Grinnell Street #4 Key West, FL Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3...	3 beds \| 2 baths \| 784 sq.ft.	$1,300,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 0.86% Airbnb Rental Income: $12642 Traditional Rental Income: $2998 Airbnb ROI: 6.94% Traditional ROI: 0.86%
710 Caroline Street Key West, FL Caroline Street, steps from the Historic Seaport. This is the Key West people picture befo...	4 beds \| 5 baths \| 2,250 sq.ft.	$3,495,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 0.53% Airbnb Rental Income: $7690 Traditional Rental Income: $6089 Airbnb ROI: 0.57% Traditional ROI: 0.53%
1222 Florida Street Key West, FL Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned ...	3 beds \| 1 baths \| 1,580 sq.ft.	$895,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 3.47% Airbnb Rental Income: $11827 Traditional Rental Income: $4737 Airbnb ROI: 8.82% Traditional ROI: 3.47%
719 Elizabeth Street Key West, FL Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Par...	3 beds \| 1 baths \| 943 sq.ft.	$1,196,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 1.97% Airbnb Rental Income: $12642 Traditional Rental Income: $4404 Airbnb ROI: 7.31% Traditional ROI: 1.97%
1405-1409 #ed Street Key West, FL Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently ...	3 beds \| 3 baths \| 1,872 sq.ft.	$2,790,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 1.14% Airbnb Rental Income: $11827 Traditional Rental Income: $6229 Airbnb ROI: 2.42% Traditional ROI: 1.14%
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: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $8144 Airbnb ROI: N/A Traditional ROI: 2.97%
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.	$1,195,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 2.39% Airbnb Rental Income: $12642 Traditional Rental Income: $4639 Airbnb ROI: 7.52% Traditional ROI: 2.39%
1113 Stump Lane Key West, FL Experience the ideal blend of historic charm and modern luxury in this fully renovated and...	4 beds \| 5 baths \| 2,985 sq.ft.	$4,450,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.19% Airbnb Rental Income: $15808 Traditional Rental Income: $10125 Airbnb ROI: 1.89% Traditional ROI: 1.19%
1719 Laird Street Key West, FL Key West Pool Home on a Double Lot -- 4 Bedroom, 3 Bathroom CBS, Parking for 4 ALL THE...	4 beds \| 3 baths \| 2,276 sq.ft.	$1,850,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.09% Airbnb Rental Income: $5911 Traditional Rental Income: $7617 Airbnb ROI: 1.41% Traditional ROI: 3.09%
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 \| 3,000 sq.ft.	$6,850,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -0.8% Airbnb Rental Income: $10441 Traditional Rental Income: $8263 Airbnb ROI: -0.77% Traditional ROI: -0.8%
524 Southard Street Key West, FL Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town ...	3 beds \| 3 baths \| 2,262 sq.ft.	$3,100,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.94% Airbnb Rental Income: $10441 Traditional Rental Income: $7056 Airbnb ROI: 1.45% Traditional ROI: 0.94%
600 Elizabeth Street Key West, FL **31 photos have been virtually staged and enhanced to assist buyers in visualizing design...	4 beds \| 6 baths \| 3,092 sq.ft.	$4,300,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.45% Airbnb Rental Income: $11427 Traditional Rental Income: $10697 Airbnb ROI: 1.1% Traditional ROI: 1.45%
1505 Johnson Street Key West, FL POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This ...	3 beds \| 3 baths \| 1,489 sq.ft.	$1,474,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 2.75% Airbnb Rental Income: $9339 Traditional Rental Income: $5897 Airbnb ROI: 3.99% Traditional ROI: 2.75%
738 Olivia Street Key West, FL Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully r...	1 beds \| 2 baths \| 767 sq.ft.	$1,100,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.26% Airbnb Rental Income: $5797 Traditional Rental Income: $3710 Airbnb ROI: 3.17% Traditional ROI: 2.26%
709 Eaton Street Key West, FL Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously pre...	4 beds \| 5 baths \| 2,716 sq.ft.	$4,695,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.63% Airbnb Rental Income: $7690 Traditional Rental Income: $10085 Airbnb ROI: -0.26% Traditional ROI: 0.63%
818 Elizabeth Street #Front Key West, FL Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, bl...	3 beds \| 3 baths \| 1,520 sq.ft.	$949,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 2.97% Airbnb Rental Income: $12642 Traditional Rental Income: $5971 Airbnb ROI: 7.7% Traditional ROI: 2.97%
1513 Pine Street Key West, FL Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully ...	2 beds \| 3 baths \| 1,717 sq.ft.	$1,899,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 1.14% Airbnb Rental Income: $8317 Traditional Rental Income: $5354 Airbnb ROI: 1.93% Traditional ROI: 1.14%
1501 Georgia Street Key West, FL 1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune a...	4 beds \| 5 baths \| 2,810 sq.ft.	$3,599,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.33% Airbnb Rental Income: $12492 Traditional Rental Income: $9846 Airbnb ROI: 1.44% Traditional ROI: 1.33%
1211 Knowles Lane Key West, FL Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled histor...	3 beds \| 3 baths \| 1,284 sq.ft.	$1,475,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 2.61% Airbnb Rental Income: $12399 Traditional Rental Income: $5641 Airbnb ROI: 5.89% Traditional ROI: 2.61%
2924 Riviera Drive Key West, FL Seller Financing Considered 2924 Riviera Dr is a Must See! Meticulously renovated hous...	3 beds \| 3 baths \| 2,469 sq.ft.	$2,549,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.49% Airbnb Rental Income: $6800 Traditional Rental Income: $9019 Airbnb ROI: 0.99% Traditional ROI: 2.49%
1620 Jamaica Drive Key West, FL NEW PRICE!! Key West WATERFRONT Home with a POOL! This expansive two-story residence has e...	4 beds \| 3 baths \| 2,080 sq.ft.	$1,995,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 2.36% Airbnb Rental Income: $11137 Traditional Rental Income: $7283 Airbnb ROI: 3.33% Traditional ROI: 2.36%
3011 Riviera Drive Key West, FL Welcome to 3011 Riviera Drive, nestled in the sought-after Riviera Shores neighborhood of ...	3 beds \| 2 baths \| 1,062 sq.ft.	$899,000	Airbnb cash on cash: 9.1% Traditional cash on cash: 4.32% Airbnb Rental Income: $11137 Traditional Rental Income: $5096 Airbnb ROI: 9.1% Traditional ROI: 4.32%
3513 Sunrise Drive Key West, FL Wake up in Key West and own your own piece of the island! Come enjoy a second-home outdoor...	3 beds \| 3 baths \| 2,569 sq.ft.	$2,165,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.26% Airbnb Rental Income: $6800 Traditional Rental Income: $7891 Airbnb ROI: 1.06% Traditional ROI: 2.26%
1019 Eaton Street Key West, FL Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home i...	3 beds \| 2 baths \| 1,458 sq.ft.	$1,880,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 1.18% Airbnb Rental Income: $11183 Traditional Rental Income: $5409 Airbnb ROI: 3.2% Traditional ROI: 1.18%
5 Sunset Key Drive Key West, FL Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless t...	3 beds \| 3 baths \| 2,528 sq.ft.	$7,000,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -1.36% Airbnb Rental Income: $11471 Traditional Rental Income: $6779 Airbnb ROI: -0.96% Traditional ROI: -1.36%
3700 Northside Drive Key West, FL This move-in ready property offers the perfect blend of comfort, functionality, and island...	3 beds \| 2 baths \| 1,411 sq.ft.	$950,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.91% Airbnb Rental Income: $6800 Traditional Rental Income: $5049 Airbnb ROI: 4.4% Traditional ROI: 3.91%
1524 5Th Street Key West, FL Welcome to your dream home in Midtown Key West! This 4-bedroom, 3-bathroom currently being...	4 beds \| 3 baths \| 1,580 sq.ft.	$939,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 4.89% Airbnb Rental Income: $5911 Traditional Rental Income: $5575 Airbnb ROI: 3.94% Traditional ROI: 4.89%
1109 Stump Lane Key West, FL On a quiet lane in Old Town, this classic Conch home offers a setting where life feels jus...	3 beds \| 3 baths \| 1,724 sq.ft.	$2,249,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 1.24% Airbnb Rental Income: $12642 Traditional Rental Income: $6695 Airbnb ROI: 2.95% Traditional ROI: 1.24%
1319 Newton Street Key West, FL Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key...	3 beds \| 2 baths \| 1,512 sq.ft.	$1,750,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 0.77% Airbnb Rental Income: $11387 Traditional Rental Income: $3935 Airbnb ROI: 4.07% Traditional ROI: 0.77%
2309 Flagler Avenue Key West, FL Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Cent...	3 beds \| 2 baths \| 1,720 sq.ft.	$1,095,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 2.18% Airbnb Rental Income: $9339 Traditional Rental Income: $3965 Airbnb ROI: 5.75% Traditional ROI: 2.18%
2412 Linda Avenue Key West, FL Waterfront, turnkey, and completely private 2412 Linda Avenue delivers the ultimate Key We...	2 beds \| 2 baths \| 1,638 sq.ft.	$1,799,999	Airbnb cash on cash: 2.26% Traditional cash on cash: 0.5% Airbnb Rental Income: $8293 Traditional Rental Income: $3769 Airbnb ROI: 2.26% Traditional ROI: 0.5%
214 Eanes Lane Key West, FL Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, an...	4 beds \| 4 baths \| 2,573 sq.ft.	$3,300,000	Airbnb cash on cash: 0.59% Traditional cash on cash: -0.7% Airbnb Rental Income: $7981 Traditional Rental Income: $2521 Airbnb ROI: 0.59% Traditional ROI: -0.7%
846 Olivia Street Key West, FL Historic Old Town Key West home offering character, a prime location, and strong potential...	3 beds \| 3 baths \| 1,804 sq.ft.	$1,249,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.24% Airbnb Rental Income: $12642 Traditional Rental Income: $5853 Airbnb ROI: 7.11% Traditional ROI: 3.24%
2805 Flagler Avenue Key West, FL This sophisticated residence features off-street parking for two vehicles or a boat and is...	3 beds \| 2 baths \| 1,227 sq.ft.	$874,999	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.25% Airbnb Rental Income: $6800 Traditional Rental Income: $3309 Airbnb ROI: 4.91% Traditional ROI: 2.25%
810 Carey Lane Key West, FL Tucked away on a quiet private lane, this charming classic Key West cottage offers the per...	3 beds \| 2 baths \| 1,200 sq.ft.	$2,150,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 0.2% Airbnb Rental Income: $12642 Traditional Rental Income: $3307 Airbnb ROI: 3.73% Traditional ROI: 0.2%

Your search for investment property begins and ends here

Single Family Homes for Sale in Key West, FL

1607 Sunshine Drive

Key West, FL

3 beds | 3 baths | 1,672 sq.ft.

$1,969,000

Airbnb cash on cash: 3.91%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $11827

Traditional Rental Income: $5163

Airbnb ROI: 3.91%

Traditional ROI: 1.45%

1115 Fleming Street

Key West, FL

4 beds | 2 baths | 1,760 sq.ft.

$1,875,000

Airbnb cash on cash: 1.78%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $7690

Traditional Rental Income: $5932

Airbnb ROI: 1.78%

Traditional ROI: 1.62%

1500 5th Street

Key West, FL

4 beds | 2 baths | 2,111 sq.ft.

$979,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $5911

Traditional Rental Income: $4419

Airbnb ROI: 3.9%

Traditional ROI: 3.56%

1105 Olivia Street

Key West, FL

1 beds | 1 baths | 622 sq.ft.

$819,000

Airbnb cash on cash: 4.21%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $5797

Traditional Rental Income: $1985

Airbnb ROI: 4.21%

Traditional ROI: 1.04%

817 Terry Lane

Key West, FL

1 beds | 1 baths | 420 sq.ft.

$935,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 2%

Airbnb Rental Income: $5429

Traditional Rental Income: $3425

Airbnb ROI: 2.98%

Traditional ROI: 2%

611 Grinnell Street #4

Key West, FL

3 beds | 2 baths | 784 sq.ft.

$1,300,000

Airbnb cash on cash: 6.94%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $12642

Traditional Rental Income: $2998

Airbnb ROI: 6.94%

Traditional ROI: 0.86%

710 Caroline Street

Key West, FL

4 beds | 5 baths | 2,250 sq.ft.

$3,495,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $7690

Traditional Rental Income: $6089

Airbnb ROI: 0.57%

Traditional ROI: 0.53%

1222 Florida Street

Key West, FL

3 beds | 1 baths | 1,580 sq.ft.

$895,000

Airbnb cash on cash: 8.82%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $11827

Traditional Rental Income: $4737

Airbnb ROI: 8.82%