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 127 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
68 Sunset Key Drive Key West, FL Surprising water views combined with maximum privacy are the signature advantages of this ...	2 beds \| 3 baths \| 1,681 sq.ft.	$2,600,000	Airbnb cash on cash: 0.29% Traditional cash on cash: -0.85% Airbnb Rental Income: $9360 Traditional Rental Income: $4858 Airbnb ROI: 0.29% Traditional ROI: -0.85%
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.	$1,975,000	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%
1105 Olivia Street Key West, FL Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Tow...	1 beds \| 1 baths \| 619 sq.ft.	$899,900	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%
1500 5th Street Key West, FL Substantial concrete 4-bedroom, 2-bath home featuring a dedicated office, offering an exce...	4 beds \| 2 baths \| 2,111 sq.ft.	$979,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.56% Airbnb Rental Income: $4234 Traditional Rental Income: $4419 Airbnb ROI: 2.37% Traditional ROI: 3.56%
817 Terry Lane Key West, FL Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cot...	1 beds \| 1 baths \| 420 sq.ft.	$998,000	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%
710 Caroline Street Key West, FL An extraordinary opportunity to own one of Key West's most coveted addresses -- iconic Car...	4 beds \| 5 baths \| 2,250 sq.ft.	$3,595,000	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%
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%
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.	$990,000	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.	$2,895,000	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%
1718 #ed Street Key West, FL Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offer...	3 beds \| 3 baths \| 1,477 sq.ft.	$1,265,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 3.62% Airbnb Rental Income: $7887 Traditional Rental Income: $6047 Airbnb ROI: 3.91% Traditional ROI: 3.62%
3206 Riviera Drive Key West, FL Welcome to 3206 Riviera Drive, Key West - a stunning canal-front retreat designed for the ...	3 beds \| 3 baths \| 2,212 sq.ft.	$2,699,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.66% Airbnb Rental Income: $6800 Traditional Rental Income: $7162 Airbnb ROI: 0.99% Traditional ROI: 1.66%
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%
2311 Patterson Avenue Key West, FL Your private island retreat awaits. Discover the ultimate in low-maintenance living with t...	3 beds \| 2 baths \| 1,356 sq.ft.	$999,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 3.89% Airbnb Rental Income: $7887 Traditional Rental Income: $5163 Airbnb ROI: 5.2% Traditional ROI: 3.89%
1706 Seminary Street Key West, FL Tucked behind a new privacy fence, 1706 Seminary Street is a fully renovated home where th...	3 beds \| 3 baths \| 1,938 sq.ft.	$2,089,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 2.01% Airbnb Rental Income: $7887 Traditional Rental Income: $6777 Airbnb ROI: 1.81% Traditional ROI: 2.01%
1010 Olivia Street Key West, FL Introducing The Twins on Olivia - a storied Key West treasure reborn. Once known locally a...	3 beds \| 4 baths \| 2,421 sq.ft.	$3,999,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 0.54% Airbnb Rental Income: $12642 Traditional Rental Income: $6609 Airbnb ROI: 1.55% Traditional ROI: 0.54%
1719 Laird Street Key West, FL Pool. Space. Privacy. -- Rare Double Lot Living in Key West 1719 Laird Street offers the s...	4 beds \| 3 baths \| 2,276 sq.ft.	$1,850,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.09% Airbnb Rental Income: $4234 Traditional Rental Income: $7617 Airbnb ROI: 0.6% 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%
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.	$1,499,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 2.69% Airbnb Rental Income: $7887 Traditional Rental Income: $5897 Airbnb ROI: 3.04% Traditional ROI: 2.69%
600 Elizabeth Street Key West, FL **The first 31 photos have been virtually staged and enhanced to assist buyers in visualiz...	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%
1427 Washington Street Key West, FL Located in a charming midtown neighborhood sits this beautifully renovated 4BD/2.5BA Key W...	4 beds \| 3 baths \| 2,051 sq.ft.	$2,525,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 1.11% Airbnb Rental Income: $9630 Traditional Rental Income: $5909 Airbnb ROI: 1.94% Traditional ROI: 1.11%
1712 Laird Street Key West, FL Located in the heart of Key West, 1712 Laird Street offers a rare blend of central conveni...	3 beds \| 2 baths \| 1,378 sq.ft.	$1,284,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.99% Airbnb Rental Income: $7887 Traditional Rental Income: $5243 Airbnb ROI: 3.95% Traditional ROI: 2.99%
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%
910-914 Watson Street Key West, FL More than a residence and rarer than legend, 910-914 Watson Street stands as one of the mo...	5 beds \| 7 baths \| 4,387 sq.ft.	$5,995,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.97% Airbnb Rental Income: $7009 Traditional Rental Income: $15005 Airbnb ROI: -0.71% Traditional ROI: 0.97%
3700 Eagle Avenue Key West, FL Set on the highly desirable upper end of Eagle Avenue, this four bedroom, three bath home ...	4 beds \| 3 baths \| 2,733 sq.ft.	$1,689,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 2.76% Airbnb Rental Income: $11137 Traditional Rental Income: $6958 Airbnb ROI: 4.12% Traditional ROI: 2.76%
3 Nassau Lane #A Key West, FL Charming Key West Cottage on Historic Nassau Lane Nestled along the picturesque and histor...	1 beds \| 1 baths \| 468 sq.ft.	$825,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 2.68% Airbnb Rental Income: $5797 Traditional Rental Income: $3397 Airbnb ROI: 4.3% Traditional ROI: 2.68%
1209 Packer Street Key West, FL Discover a seamless blend of historic character and modern refinement at 1209 Packer Stree...	4 beds \| 4 baths \| 2,150 sq.ft.	$2,175,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 1.79% Airbnb Rental Income: $12492 Traditional Rental Income: $7021 Airbnb ROI: 3.37% Traditional ROI: 1.79%
1505 Rose Street Key West, FL Welcome to 1505 Rose Street in Key West, Florida! This legal duplex is perfect -- feels ju...	4 beds \| 3 baths \| 1,932 sq.ft.	$1,785,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.43% Airbnb Rental Income: $4234 Traditional Rental Income: $6591 Airbnb ROI: 0.46% Traditional ROI: 2.43%
1422 Catherine Street Key West, FL Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of ...	2 beds \| 2 baths \| 548 sq.ft.	$850,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 3.78% Airbnb Rental Income: $9630 Traditional Rental Income: $4240 Airbnb ROI: 8.33% Traditional ROI: 3.78%
2012 Roosevelt Drive Key West, FL Spacious and well-designed 3-bedroom, 2-bathroom home offering a flexible and functional f...	3 beds \| 2 baths \| 1,515 sq.ft.	$899,000	Airbnb cash on cash: 6.19% Traditional cash on cash: 5.11% Airbnb Rental Income: $7887 Traditional Rental Income: $5479 Airbnb ROI: 6.19% Traditional ROI: 5.11%
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.	$995,000	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%
1610 Laird Street Key West, FL This property can also be purchased along with the adjacent property 1612 Laird. Owner fin...	3 beds \| 2 baths \| 1,721 sq.ft.	$1,354,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.03% Airbnb Rental Income: $7887 Traditional Rental Income: $5953 Airbnb ROI: 3.38% Traditional ROI: 3.03%
413 Frances Street Key West, FL Extraordinary home in the historic district! Enjoy Key West living in the prized Old Town ...	3 beds \| 3 baths \| 1,536 sq.ft.	$2,240,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 1.1% Airbnb Rental Income: $11183 Traditional Rental Income: $5785 Airbnb ROI: 2.71% Traditional ROI: 1.1%
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: 2.27% Traditional cash on cash: 1.14% Airbnb Rental Income: $9037 Traditional Rental Income: $5354 Airbnb ROI: 2.27% 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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Key West, FL

68 Sunset Key Drive

Key West, FL

2 beds | 3 baths | 1,681 sq.ft.

$2,600,000

Airbnb cash on cash: 0.29%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $9360

Traditional Rental Income: $4858

Airbnb ROI: 0.29%

Traditional ROI: -0.85%

1115 Fleming Street

Key West, FL

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

$1,975,000

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%

1105 Olivia Street

Key West, FL

1 beds | 1 baths | 619 sq.ft.

$899,900

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%

1500 5th Street

Key West, FL

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

$979,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4234

Traditional Rental Income: $4419

Airbnb ROI: 2.37%

Traditional ROI: 3.56%

817 Terry Lane

Key West, FL

1 beds | 1 baths | 420 sq.ft.

$998,000

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%

710 Caroline Street

Key West, FL

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

$3,595,000

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%

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%

1222 Florida Street

Key West, FL

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

$990,000

Airbnb cash on cash: 8.82%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $11827

Traditional Rental Income: $4737

Airbnb ROI: 8.82%