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%
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: -0.39% Traditional cash on cash: -0.85% Airbnb Rental Income: $7399 Traditional Rental Income: $4858 Airbnb ROI: -0.39% 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: 3.03% Traditional cash on cash: 1.62% Airbnb Rental Income: $10441 Traditional Rental Income: $5932 Airbnb ROI: 3.03% Traditional ROI: 1.62%
1422 Patricia Street Key West, FL Situated on a 6,000 sq. ft. corner lot just one block from the Atlantic Ocean, this elevat...	3 beds \| 4 baths \| 1,865 sq.ft.	$2,199,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.74% Airbnb Rental Income: $2385 Traditional Rental Income: $7495 Airbnb ROI: -1.05% Traditional ROI: 1.74%
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%
3930 S Roosevelt Boulevard #UNIT N401 Key West, FL Experience penthouse living at Las Salinas in one of the largest two-bedroom residences av...	2 beds \| 2 baths \| 1,073 sq.ft.	$525,000	Airbnb cash on cash: 9.1% Traditional cash on cash: 5.82% Airbnb Rental Income: $7456 Traditional Rental Income: $4413 Airbnb ROI: 9.1% Traditional ROI: 5.82%
1519 Johnson Street Key West, FL Discover the perfect blend of modern elegance and island charm in this updated 5-bedroom, ...	5 beds \| 4 baths \| 2,366 sq.ft.	$2,290,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $8357 Airbnb ROI: N/A Traditional ROI: 2.4%
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.	$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: 0.55% Traditional cash on cash: 3.69% Airbnb Rental Income: $2938 Traditional Rental Income: $5178 Airbnb ROI: 0.55% Traditional ROI: 3.69%
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%
3301 Duck Avenue #UNIT 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%
3841 N Roosevelt Boulevard #UNIT 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 #UNIT 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: 2.73% Traditional cash on cash: -0.63% Airbnb Rental Income: $11088 Traditional Rental Income: $5932 Airbnb ROI: 2.73% Traditional ROI: -0.63%
3841 N Roosevelt Boulevard #UNIT 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%
1311 Grinnell Street Key West, FL Historic Casa Marina Gem - Fully Restored & Furnished! Experience timeless Key West charm...	5 beds \| 7 baths \| 2,681 sq.ft.	$4,250,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.15% Airbnb Rental Income: $16799 Traditional Rental Income: $9390 Airbnb ROI: 2.27% Traditional ROI: 1.15%
1114 Packer Street Key West, FL Best Priced 5-Bedroom Compound in Key West \| Renovated Old Town Home with Detached Guest H...	5 beds \| 5 baths \| 2,721 sq.ft.	$3,075,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.02% Airbnb Rental Income: $11896 Traditional Rental Income: $9847 Airbnb ROI: 1.98% Traditional ROI: 2.02%
22 Merganser Lane Key West, FL Motivated Seller ! Exquisite finishes & attention to detail in the overall design of this ...	2 beds \| 2 baths \| 780 sq.ft.	$680,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 3.3% Airbnb Rental Income: $7456 Traditional Rental Income: $3831 Airbnb ROI: 6.76% Traditional ROI: 3.3%
90 Golf Club Drive Key West, FL Seller Motivated. This charming Poolside Key West Golf Club home is ready for you to make ...	2 beds \| 3 baths \| 930 sq.ft.	$719,000	Airbnb cash on cash: 6.95% Traditional cash on cash: 4.29% Airbnb Rental Income: $7456 Traditional Rental Income: $4241 Airbnb ROI: 6.95% Traditional ROI: 4.29%
1616 Atlantic Boulevard #UNIT 6 Key West, FL This is the one you've been waiting for! Unlike any other 2 bed listing available in Casa ...	2 beds \| 3 baths \| 1,940 sq.ft.	$1,999,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 1.25% Airbnb Rental Income: $3408 Traditional Rental Income: $5869 Airbnb ROI: -0.49% Traditional ROI: 1.25%
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.	$1,199,000	Airbnb cash on cash: 6.6% Traditional cash on cash: 1.96% Airbnb Rental Income: $11712 Traditional Rental Income: $4404 Airbnb ROI: 6.6% Traditional ROI: 1.96%
421 - 423 Simonton Street Key West, FL Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, ...	6 beds \| 8 baths \| 3,010 sq.ft.	$5,850,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 0.77% Airbnb Rental Income: $12364 Traditional Rental Income: $12125 Airbnb ROI: 0.4% Traditional ROI: 0.77%
3300 Riviera Drive Key West, FL Welcome to 3300 Riviera Drive--an exceptional, turn-key, waterfront, residential estate fe...	4 beds \| 5 baths \| 3,577 sq.ft.	$4,785,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 1.41% Airbnb Rental Income: $9315 Traditional Rental Income: $12234 Airbnb ROI: 0.36% Traditional ROI: 1.41%
1124 Catherine Street #UNIT 202 Key West, FL This bright and well-maintained condo offers the perfect blend of comfort and convenience ...	2 beds \| 1 baths \| 677 sq.ft.	$579,000	Airbnb cash on cash: -2.21% Traditional cash on cash: 1.62% Airbnb Rental Income: $1999 Traditional Rental Income: $3549 Airbnb ROI: -2.21% Traditional ROI: 1.62%
202 Admirals Lane Key West, FL Located in a gated community within the highly sought-after Truman Annex in Old Town Key W...	5 beds \| 4 baths \| 3,148 sq.ft.	$4,350,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 0.17% Airbnb Rental Income: $11896 Traditional Rental Income: $8025 Airbnb ROI: 0.6% 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.	$1,680,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 2.42% Airbnb Rental Income: $11580 Traditional Rental Income: $6631 Airbnb ROI: 4.23% Traditional ROI: 2.42%
408 William Street Key West, FL Blending timeless character and modern comfort this home is nestled on one of Old Town's m...	4 beds \| 3 baths \| 1,943 sq.ft.	$1,800,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 1.62% Airbnb Rental Income: $10441 Traditional Rental Income: $5675 Airbnb ROI: 3.31% Traditional ROI: 1.62%
1606 Flagler Avenue Key West, FL Incredible value for this Midtown Key West Renovated Home \| 2BR/2BA \| Off-Street Parking \|...	2 beds \| 2 baths \| 1,118 sq.ft.	$950,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.41% Airbnb Rental Income: $3408 Traditional Rental Income: $4619 Airbnb ROI: 1.19% Traditional ROI: 3.41%
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: 3.63% Traditional cash on cash: 3.35% Airbnb Rental Income: $11712 Traditional Rental Income: $9077 Airbnb ROI: 3.63% 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.	$1,350,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.33% Airbnb Rental Income: $2385 Traditional Rental Income: $6047 Airbnb ROI: -0.05% Traditional ROI: 3.33%
115 Front Street #UNIT 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.	$2,250,000	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 #UNIT 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: 1.18% Traditional cash on cash: 3.24% Airbnb Rental Income: $3477 Traditional Rental Income: $4613 Airbnb ROI: 1.18% 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/...	2 beds \| 4 baths \| 1,596 sq.ft.	$2,999,999	Airbnb cash on cash: 0.73% Traditional cash on cash: 0.61% Airbnb Rental Income: $6911 Traditional Rental Income: $5224 Airbnb ROI: 0.73% Traditional ROI: 0.61%
2016 Fogarty Avenue Key West, FL Welcome to 2016 Fogarty Avenue in Midtown Key West -- a charming 2-bedroom, 1-bath wood-fr...	2 beds \| 1 baths \| 1,292 sq.ft.	$775,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.77% Airbnb Rental Income: $3408 Traditional Rental Income: $4441 Airbnb ROI: 2.29% Traditional ROI: 4.77%
3841 N Roosevelt Boulevard #UNIT 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: -0.78% Traditional cash on cash: -1.38% Airbnb Rental Income: $7456 Traditional Rental Income: $4942 Airbnb ROI: -0.78% Traditional ROI: -1.38%
3841 N Roosevelt Boulevard #UNIT 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: -0.77% Traditional cash on cash: -1.37% Airbnb Rental Income: $7456 Traditional Rental Income: $4942 Airbnb ROI: -0.77% Traditional ROI: -1.37%

Real Estate investment in Key-west, FL

There are 187 properties for sale in the city of Key West . The median list price in Key West is $1,352,000 and the average price per square foot is $814. In May 2026, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $3,307.

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

There are 187 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 $2,938.

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%

68 Sunset Key Drive

Key West, FL

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

$2,600,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $7399

Traditional Rental Income: $4858

Airbnb ROI: -0.39%

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: 3.03%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $10441

Traditional Rental Income: $5932

Airbnb ROI: 3.03%

Traditional ROI: 1.62%

1422 Patricia Street

Key West, FL

3 beds | 4 baths | 1,865 sq.ft.

$2,199,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: 1.74%

Airbnb Rental Income: $2385

Traditional Rental Income: $7495

Airbnb ROI: -1.05%

Traditional ROI: 1.74%

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%

3930 S Roosevelt Boulevard #UNIT N401

Key West, FL

2 beds | 2 baths | 1,073 sq.ft.

$525,000

Airbnb cash on cash: 9.1%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $7456

Traditional Rental Income: $4413

Airbnb ROI: 9.1%

Traditional ROI: 5.82%

1519 Johnson Street

Key West, FL

5 beds | 4 baths | 2,366 sq.ft.

$2,290,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.4%

Airbnb Rental Income: $null

Traditional Rental Income: $8357

Airbnb ROI: N/A

Traditional ROI: 2.4%

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%