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.

Investment Property for Sale in Key West, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
85 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$459,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 10.33% Airbnb Rental Income: $5523 Traditional Rental Income: $5325 Airbnb ROI: 8.21% Traditional ROI: 10.33%
58 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 8.46% Airbnb Rental Income: $5523 Traditional Rental Income: $5325 Airbnb ROI: 6.68% Traditional ROI: 8.46%
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.	$1,775,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.91% Airbnb Rental Income: $8075 Traditional Rental Income: $5932 Airbnb ROI: 2.28% Traditional ROI: 1.91%
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: 5.47% Traditional cash on cash: 3.56% Airbnb Rental Income: $7621 Traditional Rental Income: $4419 Airbnb ROI: 5.47% Traditional ROI: 3.56%
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: 1.74% Traditional cash on cash: 2.2% Airbnb Rental Income: $3864 Traditional Rental Income: $3425 Airbnb ROI: 1.74% Traditional ROI: 2.2%
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: 5.49% Traditional cash on cash: 0.86% Airbnb Rental Income: $10540 Traditional Rental Income: $2998 Airbnb ROI: 5.49% Traditional ROI: 0.86%
3365 Flagler Avenue Key West, FL Not your cookie-cutter Key West townhome! This thoughtfully updated 2-bedroom, 2-bath home...	2 beds \| 2 baths \| 1,339 sq.ft.	$860,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.06% Airbnb Rental Income: $5523 Traditional Rental Income: $4675 Airbnb ROI: 3.73% Traditional ROI: 4.06%
806 Florida Street #Apt 5 Key West, FL 1 bedrooms and 1 bathrooms, you are going to enjoy the 626 sqft that composes this Condomi...	1 beds \| 1 baths \| 626 sq.ft.	$649,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 1.31% Airbnb Rental Income: $4306 Traditional Rental Income: $1963 Airbnb ROI: 3.68% Traditional ROI: 1.31%
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.	$1,089,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 2.26% Airbnb Rental Income: $10540 Traditional Rental Income: $4404 Airbnb ROI: 6.4% Traditional ROI: 2.26%
909 Grinnell Street Key West, FL Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's c...	7 beds \| 6 baths \| 2,790 sq.ft.	$1,899,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.35% Airbnb Rental Income: $8720 Traditional Rental Income: $9077 Airbnb ROI: 2.22% Traditional ROI: 3.35%
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: 3.25% Traditional cash on cash: 1.22% Airbnb Rental Income: $13976 Traditional Rental Income: $6229 Airbnb ROI: 3.25% Traditional ROI: 1.22%
3312 Northside Drive #405 Key West, FL IMPORTANT UPDATE TO NOTE: SELLER IS OFFERING A $5,000 BUYER CREDIT THAT CAN BE USED FOR CL...	1 beds \| 1 baths \| 528 sq.ft.	$343,400	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.43% Airbnb Rental Income: $2590 Traditional Rental Income: $1357 Airbnb ROI: 4.33% Traditional ROI: 2.43%
405 Petronia Street Key West, FL Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/...	N/A beds \| 4 baths \| 1,596 sq.ft.	$2,999,999	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.63% Airbnb Rental Income: $1396 Traditional Rental Income: $5224 Airbnb ROI: -0.89% Traditional ROI: 0.63%
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.	$1,449,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 2.82% Airbnb Rental Income: $7776 Traditional Rental Income: $5897 Airbnb ROI: 3.11% Traditional ROI: 2.82%
2601 S Roosevelt Boulevard #406A Key West, FL Ocean Views from this beautifully 2br/1.5ba renovated Key West by The Sea condo on Smather...	2 beds \| 2 baths \| 980 sq.ft.	$926,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.95% Airbnb Rental Income: $5523 Traditional Rental Income: $4150 Airbnb ROI: 2.26% Traditional ROI: 1.95%
48 Merganser Lane Key West, FL An easier way to own in Key West. This 2-bedroom, 1.5-bath townhome in the Key West Golf C...	2 beds \| 2 baths \| 780 sq.ft.	$589,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.08% Airbnb Rental Income: $5523 Traditional Rental Income: $3883 Airbnb ROI: 5.05% Traditional ROI: 4.08%
2613 Gulfview Drive Key West, FL Rare WATERFRONT home on the island of Key West, an incredible value priced well below the ...	3 beds \| 3 baths \| 1,320 sq.ft.	$1,549,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 1.22% Airbnb Rental Income: $15556 Traditional Rental Income: $4675 Airbnb ROI: 6.85% Traditional ROI: 1.22%
1203 Newton Street #1 Key West, FL Picture perfect condo located in 1 of 2 historic buildings totaling 8 units with a generou...	1 beds \| 1 baths \| 427 sq.ft.	$699,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.89% Airbnb Rental Income: $4306 Traditional Rental Income: $3357 Airbnb ROI: 1.96% Traditional ROI: 1.89%
1901 S Roosevelt Boulevard #401E Key West, FL Discover the rare opportunity to own a premier developer's unit in one of Key West's most ...	3 beds \| 2 baths \| 1,395 sq.ft.	$1,375,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 1.06% Airbnb Rental Income: $7776 Traditional Rental Income: $4915 Airbnb ROI: 2.13% Traditional ROI: 1.06%
1014 Truman Avenue #202 Key West, FL 1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West...	2 beds \| 2 baths \| 1,017 sq.ft.	$750,000	Airbnb cash on cash: 8.55% Traditional cash on cash: 1.68% Airbnb Rental Income: $9006 Traditional Rental Income: $2512 Airbnb ROI: 8.55% Traditional ROI: 1.68%
2601 S Roosevelt Boulevard #204A Key West, FL Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath resid...	1 beds \| 1 baths \| 754 sq.ft.	$599,000	Airbnb cash on cash: 0% Traditional cash on cash: 2.94% Airbnb Rental Income: $2590 Traditional Rental Income: $3615 Airbnb ROI: 0% Traditional ROI: 2.94%
2004 Patterson Avenue Key West, FL Well-maintained duplex offering flexible living and strong income potential in a desirable...	4 beds \| 3 baths \| 1,239 sq.ft.	$899,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.05% Airbnb Rental Income: $7776 Traditional Rental Income: $4958 Airbnb ROI: 5.64% Traditional ROI: 4.05%
818 Elizabeth Street Key West, FL Rare Multi-Family Investment Opportunity in Old Town Key West. This unique property is com...	8 beds \| 8 baths \| 3,797 sq.ft.	$3,650,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 1.21% Airbnb Rental Income: $8720 Traditional Rental Income: $9767 Airbnb ROI: 0.42% Traditional ROI: 1.21%
709 Eaton Street Key West, FL Old Town Seaport Grand Home Step into the enchanting world of Key West history at 709 Eato...	4 beds \| 5 baths \| 2,716 sq.ft.	$4,695,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.63% Airbnb Rental Income: $8075 Traditional Rental Income: $10085 Airbnb ROI: -0.19% Traditional ROI: 0.63%
927 Thomas Street #4 Key West, FL Located in one of Key West's newer developments at The Captains House in Bahama Village, t...	2 beds \| 1 baths \| 762 sq.ft.	$859,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 1.98% Airbnb Rental Income: $7501 Traditional Rental Income: $3944 Airbnb ROI: 4.63% Traditional ROI: 1.98%
1014 Flagler Avenue Key West, FL A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by lege...	3 beds \| 4 baths \| 3,104 sq.ft.	$4,700,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.31% Airbnb Rental Income: $10733 Traditional Rental Income: $8450 Airbnb ROI: 0.38% Traditional ROI: 0.31%
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.	$899,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.39% Airbnb Rental Income: $10540 Traditional Rental Income: $5971 Airbnb ROI: 6.53% Traditional ROI: 3.39%
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: 0.74% Traditional cash on cash: 1.14% Airbnb Rental Income: $5810 Traditional Rental Income: $5354 Airbnb ROI: 0.74% 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: 2.25% Traditional cash on cash: 1.33% Airbnb Rental Income: $15737 Traditional Rental Income: $9846 Airbnb ROI: 2.25% 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: 4.88% Traditional cash on cash: 2.61% Airbnb Rental Income: $10733 Traditional Rental Income: $5641 Airbnb ROI: 4.88% 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: 4.08% Traditional cash on cash: 2.49% Airbnb Rental Income: $15556 Traditional Rental Income: $9019 Airbnb ROI: 4.08% Traditional ROI: 2.49%
1613 Trinidad Drive Key West, FL Updated home with a bright floor plan featuring quartz counter tops, stainless steel appli...	3 beds \| 2 baths \| 1,380 sq.ft.	$1,285,000	Airbnb cash on cash: 9.1% Traditional cash on cash: 2.61% Airbnb Rental Income: $15556 Traditional Rental Income: $5023 Airbnb ROI: 9.1% Traditional ROI: 2.61%
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.	$1,975,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 2.39% Airbnb Rental Income: $5746 Traditional Rental Income: $7283 Airbnb ROI: 0.93% Traditional ROI: 2.39%
25 Kingfisher Lane Key West, FL Tucked away on a quiet private cul-de-sac in the highly sought-after Key West Golf Club co...	2 beds \| 3 baths \| 900 sq.ft.	$750,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.04% Airbnb Rental Income: $5523 Traditional Rental Income: $3963 Airbnb ROI: 3.69% Traditional ROI: 3.04%
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.	$2,100,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 2.36% Airbnb Rental Income: $15556 Traditional Rental Income: $7891 Airbnb ROI: 4.87% Traditional ROI: 2.36%
1019 Eaton Street Key West, FL Tucked within the charm of Old Town Key West, this historic Eyebrow home invites a lifesty...	3 beds \| 2 baths \| 1,458 sq.ft.	$1,799,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.42% Airbnb Rental Income: $9333 Traditional Rental Income: $5409 Airbnb ROI: 2.72% Traditional ROI: 1.42%
68 Merganser Lane Key West, FL Beautifully finished, lovingly maintained, and fully furnished 2-bedroom, 1.5-bath townhom...	2 beds \| 2 baths \| 780 sq.ft.	$648,900	Airbnb cash on cash: 4.52% Traditional cash on cash: 3.58% Airbnb Rental Income: $5523 Traditional Rental Income: $3843 Airbnb ROI: 4.52% Traditional ROI: 3.58%
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.	$919,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 5.02% Airbnb Rental Income: $7621 Traditional Rental Income: $5575 Airbnb ROI: 5.71% Traditional ROI: 5.02%
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.	$2,199,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.34% Airbnb Rental Income: $10540 Traditional Rental Income: $6695 Airbnb ROI: 2.27% Traditional ROI: 1.34%
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: 2.62% Traditional cash on cash: 0.77% Airbnb Rental Income: $8551 Traditional Rental Income: $3935 Airbnb ROI: 2.62% Traditional ROI: 0.77%

Real Estate investment in Key-west, FL

There are 158 properties for sale in the city of Key West . The median list price in Key West is $999,524 and the average price per square foot is $612. In November 2026, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $2,801.

Key-west, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 158 investment properties available for sale in Key-west.

In 2026, the best neighborhood to buy investment property is Truman Annex.

The ROI for Short-Term is higher than the Long-Term in Key-west with average rental income of $5,810.

Your search for investment property begins and ends here

Investment Property for Sale in Key West, FL

85 Golf Club Dr

Key West, FL

2 beds | 3 baths | N/A

$459,000

Airbnb cash on cash: 8.21%

Traditional cash on cash: 10.33%

Airbnb Rental Income: $5523

Traditional Rental Income: $5325

Airbnb ROI: 8.21%

Traditional ROI: 10.33%

58 Golf Club Dr

Key West, FL

2 beds | 3 baths | N/A

$549,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 8.46%

Airbnb Rental Income: $5523

Traditional Rental Income: $5325

Airbnb ROI: 6.68%

Traditional ROI: 8.46%

1115 Fleming Street

Key West, FL

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

$1,775,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $8075

Traditional Rental Income: $5932

Airbnb ROI: 2.28%

Traditional ROI: 1.91%

1500 5th Street

Key West, FL

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

$979,000

Airbnb cash on cash: 5.47%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $7621

Traditional Rental Income: $4419

Airbnb ROI: 5.47%

Traditional ROI: 3.56%

817 Terry Lane

Key West, FL

1 beds | 1 baths | 420 sq.ft.

$935,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $3864

Traditional Rental Income: $3425

Airbnb ROI: 1.74%

Traditional ROI: 2.2%

611 Grinnell Street #4

Key West, FL

3 beds | 2 baths | 784 sq.ft.

$1,300,000

Airbnb cash on cash: 5.49%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $10540

Traditional Rental Income: $2998

Airbnb ROI: 5.49%

Traditional ROI: 0.86%

3365 Flagler Avenue

Key West, FL

2 beds | 2 baths | 1,339 sq.ft.

$860,000

Airbnb cash on cash: 3.73%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $5523

Traditional Rental Income: $4675

Airbnb ROI: 3.73%

Traditional ROI: 4.06%

806 Florida Street #Apt 5

Key West, FL

1 beds | 1 baths | 626 sq.ft.

$649,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $4306

Traditional Rental Income: $1963

Airbnb ROI: 3.68%