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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1401 Simonton Street #UNIT 14 Key West, FL This second-floor luxury condo is ideally situated just one block from the beach and the i...	2 beds \| 2 baths \| 958 sq.ft.	$2,000,000	Airbnb cash on cash: 2.03% Traditional cash on cash: -0.41% Airbnb Rental Income: $8279 Traditional Rental Income: $2184 Airbnb ROI: 2.03% Traditional ROI: -0.41%
702 Florida Street Key West, FL BRAND NEW ROOF with new Kitchen Skylights! This beautiful single-story CBS home is on a de...	2 beds \| 2 baths \| 1,458 sq.ft.	$1,290,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 1.17% Airbnb Rental Income: $8836 Traditional Rental Income: $3464 Airbnb ROI: 4.26% Traditional ROI: 1.17%
224 Golf Club Drive Key West, FL Located in the coveted Sanctuary enclave of the Key West Golf Club, this fully renovated, ...	2 beds \| 3 baths \| 1,120 sq.ft.	$899,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 4.1% Airbnb Rental Income: $7456 Traditional Rental Income: $5046 Airbnb ROI: 5.27% Traditional ROI: 4.1%
1211 Catherine Street Key West, FL This charming historic home is located just steps off vibrant White St and close to the be...	3 beds \| 2 baths \| 1,463 sq.ft.	$1,680,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 0.71% Airbnb Rental Income: $10831 Traditional Rental Income: $3756 Airbnb ROI: 3.97% Traditional ROI: 0.71%
816 Ashe Street Key West, FL This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Ke...	3 beds \| 4 baths \| 1,522 sq.ft.	$2,195,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 1% Airbnb Rental Income: $11060 Traditional Rental Income: $4651 Airbnb ROI: 3.14% Traditional ROI: 1%
1104 South Street Key West, FL ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina distri...	3 beds \| 4 baths \| 2,110 sq.ft.	$2,250,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 0.56% Airbnb Rental Income: $11580 Traditional Rental Income: $5132 Airbnb ROI: 2.63% Traditional ROI: 0.56%
1124 Seminary Street Key West, FL Beautiful home in the Casa Marina District. Completely remodeled in 2020 and the guest cot...	3 beds \| 4 baths \| 1,970 sq.ft.	$2,650,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 0.57% Airbnb Rental Income: $10831 Traditional Rental Income: $5393 Airbnb ROI: 1.97% Traditional ROI: 0.57%
729 Windsor Lane Key West, FL Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rar...	2 beds \| 1 baths \| 723 sq.ft.	$1,195,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 0.34% Airbnb Rental Income: $8333 Traditional Rental Income: $2543 Airbnb ROI: 4.13% Traditional ROI: 0.34%
1014 Truman Avenue #UNIT 3 Key West, FL 1014 Truman Avenue - Modern Island Elegance in the Heart of Key WestWelcome to a Key West ...	2 beds \| 2 baths \| 1,017 sq.ft.	$799,900	Airbnb cash on cash: 5.94% Traditional cash on cash: -0.09% Airbnb Rental Income: $8333 Traditional Rental Income: $2262 Airbnb ROI: 5.94% Traditional ROI: -0.09%
247 Golf Club Drive Key West, FL Tucked inside the private gates of The Sanctuary at the Key West Golf Club, 247 Golf Club ...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,377,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 0.85% Airbnb Rental Income: $11088 Traditional Rental Income: $3894 Airbnb ROI: 4.88% Traditional ROI: 0.85%
5603 College Road #UNIT D104 Key West, FL Take advantage of this exciting new lower price and one of the best opportunities to own a...	2 beds \| 2 baths \| 1,171 sq.ft.	$1,090,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 0.13% Airbnb Rental Income: $7456 Traditional Rental Income: $2835 Airbnb ROI: 3.27% Traditional ROI: 0.13%
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.	$1,750,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.4% Airbnb Rental Income: $11580 Traditional Rental Income: $5193 Airbnb ROI: 4.02% Traditional ROI: 1.4%
243 Golf Club Drive Key West, FL MOTIVATED SELLERS Turn-key home with a history of rentals. Beautifully maintained, fully f...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,499,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 0.77% Airbnb Rental Income: $11088 Traditional Rental Income: $3914 Airbnb ROI: 4.46% Traditional ROI: 0.77%
612 Mickens Lane Key West, FL Come check out the Magic on Mickens Lane!Nestled in the heart of Old Town Key West, 612 Mi...	2 beds \| 2 baths \| 805 sq.ft.	$1,195,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 0.39% Airbnb Rental Income: $8036 Traditional Rental Income: $2283 Airbnb ROI: 4.19% Traditional ROI: 0.39%
915 Washington Street Key West, FL Located in the highly sought-after Casa Marina neighborhood, 915 Washington Street offers ...	2 beds \| 2 baths \| 1,193 sq.ft.	$1,950,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 0.27% Airbnb Rental Income: $9249 Traditional Rental Income: $3305 Airbnb ROI: 2.6% Traditional ROI: 0.27%
100 Admirals Lane Key West, FL Discover your dream home at the prestigious Truman Annex Community, situated on the serene...	3 beds \| 3 baths \| 1,426 sq.ft.	$2,949,000	Airbnb cash on cash: 1.97% Traditional cash on cash: -0.53% Airbnb Rental Income: $12364 Traditional Rental Income: $3283 Airbnb ROI: 1.97% Traditional ROI: -0.53%
532 Porter Lane Key West, FL Charming townhouse situated on Porter Lane in Presidents Walk community of the Truman Anne...	2 beds \| 2 baths \| 960 sq.ft.	$1,249,900	Airbnb cash on cash: 3.31% Traditional cash on cash: -0.46% Airbnb Rental Income: $8036 Traditional Rental Income: $2126 Airbnb ROI: 3.31% Traditional ROI: -0.46%
1211 Knowles Lane Key West, FL Discover the timeless charm of this beautifully remodeled historic home located in Old Tow...	3 beds \| 3 baths \| 1,284 sq.ft.	$1,595,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 1.12% Airbnb Rental Income: $11580 Traditional Rental Income: $3799 Airbnb ROI: 4.94% Traditional ROI: 1.12%
26 Spoonbill Way Key West, FL Nestled within the prestigious Key West Golf Club, a rare opportunity beckons with this ex...	3 beds \| 2 baths \| 1,350 sq.ft.	$1,175,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 0.38% Airbnb Rental Income: $11088 Traditional Rental Income: $2431 Airbnb ROI: 6.44% Traditional ROI: 0.38%
202 Admirals Lane Key West, FL Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after...	5 beds \| 4 baths \| 3,148 sq.ft.	$4,850,000	Airbnb cash on cash: 0.43% Traditional cash on cash: -0.58% Airbnb Rental Income: $11896 Traditional Rental Income: $5160 Airbnb ROI: 0.43% Traditional ROI: -0.58%
400 White Street Key West, FL Beautiful 3 bedroom 2.5 bath home being offered Turn-key, perfect walking location to rest...	3 beds \| 3 baths \| 1,845 sq.ft.	$1,925,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 1.07% Airbnb Rental Income: $12364 Traditional Rental Income: $4559 Airbnb ROI: 4.18% Traditional ROI: 1.07%
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: 2.29% Airbnb Rental Income: $7456 Traditional Rental Income: $3220 Airbnb ROI: 5.79% Traditional ROI: 2.29%
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: 0.7% Airbnb Rental Income: $9315 Traditional Rental Income: $5155 Airbnb ROI: 1.69% Traditional ROI: 0.7%
1011 Simonton Street #1 Key West, FL Excellent opportunity whether looking for a private residence or an investment. This cond...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,850,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 0.14% Airbnb Rental Income: $11712 Traditional Rental Income: $3415 Airbnb ROI: 3.72% Traditional ROI: 0.14%
314 Simonton Street Key West, FL Step into Key West history with this remarkable property, available for the first time in ...	8 beds \| 11 baths \| 8,472 sq.ft.	$5,500,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 0.49% Airbnb Rental Income: $11896 Traditional Rental Income: $8952 Airbnb ROI: 0.65% Traditional ROI: 0.49%
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%
2827 Harris Avenue Key West, FL Introducing a Stunning New Build (2023): A Luxury 5-Bedroom, 5-Bathroom Home Step into mod...	5 beds \| 5 baths \| 3,062 sq.ft.	$1,999,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $6647 Airbnb ROI: N/A Traditional ROI: 2.24%
90 Golf Club Drive Key West, FL This charming Poolside Key West Golf Club home is ready for you to make your very own vaca...	2 beds \| 3 baths \| 930 sq.ft.	$784,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 2.3% Airbnb Rental Income: $7456 Traditional Rental Income: $3109 Airbnb ROI: 6.29% Traditional ROI: 2.3%
1120 Stump Lane Key West, FL This beautifully renovated home greets you with a charming front porch perfect for enjoyin...	2 beds \| 2 baths \| 952 sq.ft.	$1,199,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 3.05% Airbnb Rental Income: $8836 Traditional Rental Income: $5348 Airbnb ROI: 4.68% Traditional ROI: 3.05%
2217 Harris Avenue Key West, FL Located in the heart of Key West and only 2 miles from Duval Street, this home is move in ...	3 beds \| 3 baths \| 1,446 sq.ft.	$930,000	Airbnb cash on cash: 8.8% Traditional cash on cash: 2.93% Airbnb Rental Income: $11301 Traditional Rental Income: $4144 Airbnb ROI: 8.8% Traditional ROI: 2.93%
923 Eaton Street Key West, FL Price just reduced--arguably the best value in Old Town. Welcome to 923 Eaton Street, wher...	3 beds \| 2 baths \| 1,440 sq.ft.	$1,675,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 0.31% Airbnb Rental Income: $12364 Traditional Rental Income: $3270 Airbnb ROI: 4.71% Traditional ROI: 0.31%
2601 S Roosevelt Boulevard #UNIT 103C Key West, FL New Listing! Experience resort-style living in beautiful Key West. This upgraded condomini...	2 beds \| 2 baths \| 1,221 sq.ft.	$915,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 0.83% Airbnb Rental Income: $8957 Traditional Rental Income: $2998 Airbnb ROI: 5.85% Traditional ROI: 0.83%
620 White Street Key West, FL This legal duplex offers fantastic potential with two separate units. The front unit is a ...	3 beds \| 2 baths \| 1,421 sq.ft.	$1,099,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 1.74% Airbnb Rental Income: $8836 Traditional Rental Income: $3597 Airbnb ROI: 5.24% Traditional ROI: 1.74%
817 Terry Lane Key West, FL This idyllic Old Town Key West home offers an extraordinary location and super-coveted par...	1 beds \| 1 baths \| 420 sq.ft.	$1,100,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 0.19% Airbnb Rental Income: $6911 Traditional Rental Income: $1858 Airbnb ROI: 3.82% Traditional ROI: 0.19%
1209 Truman Avenue #UNIT 2 Key West, FL Charming Old Town Condo in the Heart of Key West! Don't miss this beautifully updated and ...	1 beds \| 2 baths \| 836 sq.ft.	$719,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 0.35% Airbnb Rental Income: $6571 Traditional Rental Income: $2356 Airbnb ROI: 4.72% Traditional ROI: 0.35%
3741 Eagle Avenue Key West, FL 3741 Eagle Avenue - A Brand New Masterpiece of Coastal Luxury This stunning 3 bedroom, 3.5...	3 beds \| 4 baths \| 2,744 sq.ft.	$4,228,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 0.34% Airbnb Rental Income: $11088 Traditional Rental Income: $5901 Airbnb ROI: 1.15% Traditional ROI: 0.34%
1500 Seminary Street #UNIT 5A Key West, FL Welcome to this charming 1-bedroom, 1-bathroom apartment nestled in the heart of Key West....	1 beds \| 1 baths \| 525 sq.ft.	$575,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 0.13% Airbnb Rental Income: $6712 Traditional Rental Income: $1971 Airbnb ROI: 6.52% Traditional ROI: 0.13%
1022 Fleming Street Key West, FL Invest in Key West with this legal Duplex! Step into a piece of Key West history with this...	4 beds \| 2 baths \| 2,016 sq.ft.	$2,100,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 0.27% Airbnb Rental Income: $10441 Traditional Rental Income: $3909 Airbnb ROI: 2.63% Traditional ROI: 0.27%
1610 Von Phister Street Key West, FL Fully renovated and redefined mid-century home, perfectly tailored for modern island livin...	4 beds \| 4 baths \| 3,656 sq.ft.	$2,925,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.45% Airbnb Rental Income: $9343 Traditional Rental Income: $5293 Airbnb ROI: 1.3% Traditional ROI: 0.45%
316 Southard Street Key West, FL Located in the heart of Old Town Key West, 316 Southard Street is a meticulously renovated...	3 beds \| 4 baths \| 2,532 sq.ft.	$3,699,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 0.43% Airbnb Rental Income: $12364 Traditional Rental Income: $6105 Airbnb ROI: 1.6% Traditional ROI: 0.43%

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 $1,350,000 and the average price per square foot is $787. In September 2025, the average monthly cash on cash return in Key West is N/A%. The average monthly rental income in Key West is $3,278.

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

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

In 2025, the best neighborhood to buy investment property is Bahama Village.

The ROI for Long-Term is higher than the Short-Term in Key-west with average rental income of $3,278.

Your search for investment property begins and ends here

Investment Property for Sale in Key West, FL

1401 Simonton Street #UNIT 14

Key West, FL

2 beds | 2 baths | 958 sq.ft.

$2,000,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: -0.41%

Airbnb Rental Income: $8279

Traditional Rental Income: $2184

Airbnb ROI: 2.03%

Traditional ROI: -0.41%

702 Florida Street

Key West, FL

2 beds | 2 baths | 1,458 sq.ft.

$1,290,000

Airbnb cash on cash: 4.26%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $8836

Traditional Rental Income: $3464

Airbnb ROI: 4.26%

Traditional ROI: 1.17%

224 Golf Club Drive

Key West, FL

2 beds | 3 baths | 1,120 sq.ft.

$899,000

Airbnb cash on cash: 5.27%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $7456

Traditional Rental Income: $5046

Airbnb ROI: 5.27%

Traditional ROI: 4.1%

1211 Catherine Street

Key West, FL

3 beds | 2 baths | 1,463 sq.ft.

$1,680,000

Airbnb cash on cash: 3.97%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $10831

Traditional Rental Income: $3756

Airbnb ROI: 3.97%

Traditional ROI: 0.71%

816 Ashe Street

Key West, FL

3 beds | 4 baths | 1,522 sq.ft.

$2,195,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 1%

Airbnb Rental Income: $11060

Traditional Rental Income: $4651

Airbnb ROI: 3.14%

Traditional ROI: 1%

1104 South Street

Key West, FL

3 beds | 4 baths | 2,110 sq.ft.

$2,250,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 0.56%

Airbnb Rental Income: $11580

Traditional Rental Income: $5132

Airbnb ROI: 2.63%

Traditional ROI: 0.56%

1124 Seminary Street

Key West, FL

3 beds | 4 baths | 1,970 sq.ft.

$2,650,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $10831

Traditional Rental Income: $5393

Airbnb ROI: 1.97%

Traditional ROI: 0.57%

729 Windsor Lane

Key West, FL

2 beds | 1 baths | 723 sq.ft.

$1,195,000

Airbnb cash on cash: 4.13%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $8333

Traditional Rental Income: $2543

Airbnb ROI: 4.13%