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
58 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 9.82% Traditional cash on cash: 8.46% Airbnb Rental Income: $7456 Traditional Rental Income: $5325 Airbnb ROI: 9.82% 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.	$1,975,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 1.62% Airbnb Rental Income: $10441 Traditional Rental Income: $5932 Airbnb ROI: 3.03% 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: 5.04% Traditional cash on cash: 1.04% Airbnb Rental Income: $6628 Traditional Rental Income: $1985 Airbnb ROI: 5.04% Traditional ROI: 1.04%
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: 4.11% Airbnb Rental Income: $7456 Traditional Rental Income: $4675 Airbnb ROI: 5.79% Traditional ROI: 4.11%
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: 4.31% Traditional cash on cash: 2% Airbnb Rental Income: $6911 Traditional Rental Income: $3425 Airbnb ROI: 4.31% Traditional ROI: 2%
1018 Georgia Street Key West, FL Income producing Duplex in Old Town Key West! The Owner prefer to hold the financed note f...	3 beds \| 3 baths \| 1,452 sq.ft.	$999,999	Airbnb cash on cash: 6.6% Traditional cash on cash: 3.69% Airbnb Rental Income: $9696 Traditional Rental Income: $5178 Airbnb ROI: 6.6% Traditional ROI: 3.69%
3301 Duck Avenue #D Key West, FL 2 story Townhouse with 2 car garage, No HOA; Large Living room downstairs and Family room ...	2 beds \| 2 baths \| 1,200 sq.ft.	$725,000	Airbnb cash on cash: 7.15% Traditional cash on cash: 2.64% Airbnb Rental Income: $7456 Traditional Rental Income: $2979 Airbnb ROI: 7.15% Traditional ROI: 2.64%
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: 6.3% Traditional cash on cash: 0.86% Airbnb Rental Income: $11712 Traditional Rental Income: $2998 Airbnb ROI: 6.3% Traditional ROI: 0.86%
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: 1.25% Traditional cash on cash: 0.53% Airbnb Rental Income: $10441 Traditional Rental Income: $6089 Airbnb ROI: 1.25% 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.	$990,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.47% Airbnb Rental Income: $944 Traditional Rental Income: $4737 Airbnb ROI: -1.02% Traditional ROI: 3.47%
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: 1.29% Airbnb Rental Income: $9315 Traditional Rental Income: $6602 Airbnb ROI: 1.69% Traditional ROI: 1.29%
3841 N Roosevelt Boulevard #213 Key West, FL Discover the ultimate fusion of luxury and part time usage with this transient-licensed, 2...	2 beds \| 3 baths \| 1,357 sq.ft.	$899,000	Airbnb cash on cash: -0.48% Traditional cash on cash: -1.54% Airbnb Rental Income: $7456 Traditional Rental Income: $5142 Airbnb ROI: -0.48% Traditional ROI: -1.54%
3841 N Roosevelt Boulevard #222 Key West, FL Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathro...	3 beds \| 3 baths \| 1,586 sq.ft.	$999,000	Airbnb cash on cash: 4.53% Traditional cash on cash: -0.63% Airbnb Rental Income: $11088 Traditional Rental Income: $4258 Airbnb ROI: 4.53% Traditional ROI: -0.63%
3841 N Roosevelt Boulevard #632 Key West, FL Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includ...	2 beds \| 3 baths \| 1,357 sq.ft.	$749,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -2.67% Airbnb Rental Income: $7456 Traditional Rental Income: $5097 Airbnb ROI: -1.34% Traditional ROI: -2.67%
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: 6.62% Traditional cash on cash: 1.97% Airbnb Rental Income: $11712 Traditional Rental Income: $4404 Airbnb ROI: 6.62% Traditional ROI: 1.97%
1606 Flagler Avenue Key West, FL Renovated Midtown Key West Home \| 2BR/2BA \| 1,118 SF \| Taken to Studs in 2021 \| Off-Street...	2 beds \| 2 baths \| 1,118 sq.ft.	$910,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.6% Airbnb Rental Income: $3408 Traditional Rental Income: $4619 Airbnb ROI: 1.28% Traditional ROI: 3.6%
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: 3.72% Traditional cash on cash: 3.35% Airbnb Rental Income: $11896 Traditional Rental Income: $9077 Airbnb ROI: 3.72% 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.	$2,895,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.14% Airbnb Rental Income: $944 Traditional Rental Income: $6229 Airbnb ROI: -0.95% 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: 0.01% Traditional cash on cash: 3.62% Airbnb Rental Income: $2385 Traditional Rental Income: $6047 Airbnb ROI: 0.01% Traditional ROI: 3.62%
115 Front Street #101 Key West, FL Prior to the development of Truman Annex which was a notable Naval base located in the cen...	3 beds \| 3 baths \| 1,325 sq.ft.	$2,249,999	Airbnb cash on cash: 3.15% Traditional cash on cash: 0.42% Airbnb Rental Income: $12364 Traditional Rental Income: $4412 Airbnb ROI: 3.15% Traditional ROI: 0.42%
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: 2.42% Traditional cash on cash: 1.66% Airbnb Rental Income: $11088 Traditional Rental Income: $7162 Airbnb ROI: 2.42% Traditional ROI: 1.66%
1209 Truman Avenue #5 Key West, FL This is the one! Perfectly laid out two (2) bedroom and two (2) bathroom condo, with a den...	2 beds \| 2 baths \| 1,261 sq.ft.	$995,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 3.24% Airbnb Rental Income: $8103 Traditional Rental Income: $4613 Airbnb ROI: 5.35% Traditional ROI: 3.24%
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: 6.82% Traditional cash on cash: 2.39% Airbnb Rental Income: $11712 Traditional Rental Income: $4639 Airbnb ROI: 6.82% 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: 0.8% Traditional cash on cash: 1.19% Airbnb Rental Income: $10441 Traditional Rental Income: $10125 Airbnb ROI: 0.8% Traditional ROI: 1.19%
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: 0.55% Traditional cash on cash: 0.63% Airbnb Rental Income: $6211 Traditional Rental Income: $5224 Airbnb ROI: 0.55% Traditional ROI: 0.63%
3841 N Roosevelt Boulevard #332 Key West, FL Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor...	2 beds \| 3 baths \| 1,357 sq.ft.	$1,949,000	Airbnb cash on cash: 0.15% Traditional cash on cash: -1.09% Airbnb Rental Income: $7456 Traditional Rental Income: $3781 Airbnb ROI: 0.15% Traditional ROI: -1.09%
3841 N Roosevelt Boulevard #315 Key West, FL Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor...	2 beds \| 3 baths \| 1,357 sq.ft.	$1,949,000	Airbnb cash on cash: 0.16% Traditional cash on cash: -1.08% Airbnb Rental Income: $7456 Traditional Rental Income: $3781 Airbnb ROI: 0.16% Traditional ROI: -1.08%
1320 Eliza Street Key West, FL Welcome to the School House on Eliza! 1320 Eliza Street is a stunning corner-lot property ...	4 beds \| 3 baths \| 1,854 sq.ft.	$2,449,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 1.73% Airbnb Rental Income: $1277 Traditional Rental Income: $7255 Airbnb ROI: -1.08% Traditional ROI: 1.73%
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: 1.34% Traditional cash on cash: 0.54% Airbnb Rental Income: $11712 Traditional Rental Income: $6609 Airbnb ROI: 1.34% Traditional ROI: 0.54%
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: 0.27% Traditional cash on cash: 3.89% Airbnb Rental Income: $2385 Traditional Rental Income: $5163 Airbnb ROI: 0.27% 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: -0.56% Traditional cash on cash: 2.01% Airbnb Rental Income: $2385 Traditional Rental Income: $6777 Airbnb ROI: -0.56% Traditional ROI: 2.01%
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: -0.21% Traditional cash on cash: 3.09% Airbnb Rental Income: $2566 Traditional Rental Income: $7617 Airbnb ROI: -0.21% Traditional ROI: 3.09%
1800 Atlantic Boulevard #327C Key West, FL Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one...	2 beds \| 2 baths \| 1,311 sq.ft.	$1,700,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 0.24% Airbnb Rental Income: $3408 Traditional Rental Income: $4797 Airbnb ROI: -1.12% Traditional ROI: 0.24%
1503-1509 Seminary Street Key West, FL Opportunity awaits in the heart of Midtown Key West! This rare double-lot offering include...	2 beds \| 1 baths \| 1,640 sq.ft.	$1,000,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.91% Airbnb Rental Income: $1999 Traditional Rental Income: $4711 Airbnb ROI: -0.56% Traditional ROI: 2.91%
422 Amelia Street #L6 Key West, FL Don't miss this TRANSIENT licensed condo just steps away from the famous Duval Street. Thi...	1 beds \| 1 baths \| 405 sq.ft.	$1,250,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 1.34% Airbnb Rental Income: $6609 Traditional Rental Income: $3349 Airbnb ROI: 3.04% Traditional ROI: 1.34%
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: -0.51% Traditional cash on cash: -0.8% Airbnb Rental Income: $12364 Traditional Rental Income: $8263 Airbnb ROI: -0.51% Traditional ROI: -0.8%
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: 0.44% Airbnb Rental Income: $11896 Traditional Rental Income: $11082 Airbnb ROI: 0.22% Traditional ROI: 0.44%
512 Amelia Street Key West, FL Located just half a block off Duval Street, 512 Amelia Street is a rare offering that beau...	2 beds \| 3 baths \| 1,120 sq.ft.	$2,995,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.07% Airbnb Rental Income: $8279 Traditional Rental Income: $4289 Airbnb ROI: 0.94% Traditional ROI: 0.07%
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.	$3,168,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 0.9% Airbnb Rental Income: $12364 Traditional Rental Income: $7056 Airbnb ROI: 1.94% Traditional ROI: 0.9%

Real Estate investment in Key-west, FL

There are 210 properties for sale in the city of Key West . The median list price in Key West is $1,271,843 and the average price per square foot is $782. In June 2026, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $3,118.

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

There are 210 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 $8,103.

Your search for investment property begins and ends here

Investment Property for Sale in Key West, FL

58 Golf Club Dr

Key West, FL

2 beds | 3 baths | N/A

$549,000

Airbnb cash on cash: 9.82%

Traditional cash on cash: 8.46%

Airbnb Rental Income: $7456

Traditional Rental Income: $5325

Airbnb ROI: 9.82%

Traditional ROI: 8.46%

1115 Fleming Street

Key West, FL

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

$1,975,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $10441

Traditional Rental Income: $5932

Airbnb ROI: 3.03%

Traditional ROI: 1.62%

1105 Olivia Street

Key West, FL

1 beds | 1 baths | 619 sq.ft.

$899,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $6628

Traditional Rental Income: $1985

Airbnb ROI: 5.04%

Traditional ROI: 1.04%

3365 Flagler Avenue

Key West, FL

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

$860,000

Airbnb cash on cash: 5.79%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $7456

Traditional Rental Income: $4675

Airbnb ROI: 5.79%

Traditional ROI: 4.11%

817 Terry Lane

Key West, FL

1 beds | 1 baths | 420 sq.ft.

$998,000

Airbnb cash on cash: 4.31%

Traditional cash on cash: 2%

Airbnb Rental Income: $6911

Traditional Rental Income: $3425

Airbnb ROI: 4.31%

Traditional ROI: 2%

1018 Georgia Street

Key West, FL

3 beds | 3 baths | 1,452 sq.ft.

$999,999

Airbnb cash on cash: 6.6%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $9696

Traditional Rental Income: $5178

Airbnb ROI: 6.6%

Traditional ROI: 3.69%

3301 Duck Avenue #D

Key West, FL

2 beds | 2 baths | 1,200 sq.ft.

$725,000

Airbnb cash on cash: 7.15%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $7456

Traditional Rental Income: $2979

Airbnb ROI: 7.15%

Traditional ROI: 2.64%

611 Grinnell Street #4

Key West, FL

3 beds | 2 baths | 784 sq.ft.

$1,300,000

Airbnb cash on cash: 6.3%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $11712

Traditional Rental Income: $2998

Airbnb ROI: 6.3%