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
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% Traditional cash on cash: -0.31% Airbnb Rental Income: $7991 Traditional Rental Income: $2184 Airbnb ROI: 2% Traditional ROI: -0.31%
2911 Venetian Drive Key West, FL RARE- KEY WEST BOATING CANAL 3/3 GATED, POOL HOME GEM: 1.5M Beautiful CBS Custom 3 /3 Pool...	3 beds \| 3 baths \| 1,925 sq.ft.	$1,500,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 1.77% Airbnb Rental Income: $11834 Traditional Rental Income: $4255 Airbnb ROI: 5.66% Traditional ROI: 1.77%
51 Sunset Key Drive Key West, FL This is the ultimate living experience. You get all Historic Key West has to offer, but ar...	3 beds \| 3 baths \| 1,920 sq.ft.	$3,695,000	Airbnb cash on cash: 0.63% Traditional cash on cash: -1.48% Airbnb Rental Income: $12991 Traditional Rental Income: $3380 Airbnb ROI: 0.63% Traditional ROI: -1.48%
1401 Simonton Street #UNIT 20 Key West, FL NEW LISTING! TRANSIENT LICENSED 2BR CONDO! One of the most luxurious condominiums in Key ...	2 beds \| 2 baths \| 907 sq.ft.	$1,200,000	Airbnb cash on cash: 1.88% Traditional cash on cash: -1.98% Airbnb Rental Income: $7991 Traditional Rental Income: $2162 Airbnb ROI: 1.88% Traditional ROI: -1.98%
63 Sunset Key Drive Key West, FL Tranquil well maintained home professionally decorated on a private island five minutes of...	2 beds \| 3 baths \| 1,681 sq.ft.	$2,400,000	Airbnb cash on cash: 0.15% Traditional cash on cash: -1.36% Airbnb Rental Income: $7980 Traditional Rental Income: $3093 Airbnb ROI: 0.15% Traditional ROI: -1.36%
1701 Patricia Street Key West, FL Price Reduced $209,000.Exquisite mid-century luxury home! Fitting for the pages of noted a...	3 beds \| 3 baths \| 2,309 sq.ft.	$2,790,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 0.38% Airbnb Rental Income: $12355 Traditional Rental Income: $4543 Airbnb ROI: 2.53% Traditional ROI: 0.38%
1410 Reynolds Street Key West, FL Discover the epitome of refined Key West living in this beautifully renovated single-level...	3 beds \| 3 baths \| 2,262 sq.ft.	$3,999,999	Airbnb cash on cash: 1.06% Traditional cash on cash: -0.48% Airbnb Rental Income: $12355 Traditional Rental Income: $4415 Airbnb ROI: 1.06% Traditional ROI: -0.48%
415 Amelia Street Key West, FL This charming two-story Old Town cottage in Key West is ideally located just a half block ...	3 beds \| 2 baths \| 1,128 sq.ft.	$2,250,000	Airbnb cash on cash: 3.28% Traditional cash on cash: -0.19% Airbnb Rental Income: $12355 Traditional Rental Income: $2854 Airbnb ROI: 3.28% Traditional ROI: -0.19%
1014 Truman Avenue #UNIT 3 Key West, FL This stunning two-bedroom, two-bath condominium has just hit the market and is ready to wo...	2 beds \| 2 baths \| 1,017 sq.ft.	$845,000	Airbnb cash on cash: 5.3% Traditional cash on cash: -0.05% Airbnb Rental Income: $7991 Traditional Rental Income: $2262 Airbnb ROI: 5.3% Traditional ROI: -0.05%
1514 19Th Street Key West, FL Experience tropical breezes and island charm in this beautifully updated one-story home. S...	3 beds \| 2 baths \| 1,528 sq.ft.	$1,790,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 0.54% Airbnb Rental Income: $11834 Traditional Rental Income: $3417 Airbnb ROI: 4.31% Traditional ROI: 0.54%
2614 Seidenberg Avenue Key West, FL Charming Key West Oasis on a Quiet Cul-de-SacNestled on a quiet, dead-end street, this inv...	4 beds \| 3 baths \| 2,408 sq.ft.	$1,490,000	Airbnb cash on cash: 7.27% Traditional cash on cash: 1.9% Airbnb Rental Income: $14576 Traditional Rental Income: $4519 Airbnb ROI: 7.27% Traditional ROI: 1.9%
205 Julia Street Key West, FL Income producing opportunity close to Duval Street, Truman Waterfront Park, Hemingway Home...	3 beds \| 4 baths \| 1,264 sq.ft.	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.64% Airbnb Rental Income: $null Traditional Rental Income: $4156 Airbnb ROI: N/A Traditional ROI: 1.64%
5603 College Road #UNIT D104 Key West, FL Experience waterfront living at its finest in this beautiful, single-level unit in the exc...	2 beds \| 2 baths \| 1,171 sq.ft.	$1,150,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 0.17% Airbnb Rental Income: $7477 Traditional Rental Income: $2835 Airbnb ROI: 3.17% Traditional ROI: 0.17%
330 Julia Street Key West, FL This house is (((Bigger))) than the Hemingway House! with 4,849 square feet and made of 14...	4 beds \| 6 baths \| 4,849 sq.ft.	$6,000,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 0.22% Airbnb Rental Income: $15598 Traditional Rental Income: $7573 Airbnb ROI: 1.16% Traditional ROI: 0.22%
5601 College Road #UNIT C303 Key West, FL NEW PENTHOUSE LISTING! Resort lifestyle awaits you! Sunset Marina Condominium, a gated c...	2 beds \| 2 baths \| 1,024 sq.ft.	$1,185,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 0.28% Airbnb Rental Income: $7477 Traditional Rental Income: $3124 Airbnb ROI: 2.92% Traditional ROI: 0.28%
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: $12355 Traditional Rental Income: $3283 Airbnb ROI: 1.97% Traditional ROI: -0.53%
292 Sunset Key Drive Key West, FL Talk about views! This three-bedroom, three-bathroom waterfront home has incredible panora...	3 beds \| 3 baths \| 1,916 sq.ft.	$4,995,000	Airbnb cash on cash: 0% Traditional cash on cash: -1.48% Airbnb Rental Income: $12991 Traditional Rental Income: $3778 Airbnb ROI: 0% Traditional ROI: -1.48%
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.	$5,275,000	Airbnb cash on cash: 0.55% Traditional cash on cash: -0.63% Airbnb Rental Income: $13350 Traditional Rental Income: $5160 Airbnb ROI: 0.55% Traditional ROI: -0.63%
1407 Olivia Street Key West, FL Nestled in the heart of the coveted Meadows neighborhood, 1407 Olivia offers a perfect ble...	3 beds \| 2 baths \| 1,456 sq.ft.	$1,980,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 0.41% Airbnb Rental Income: $12355 Traditional Rental Income: $3275 Airbnb ROI: 4.12% Traditional ROI: 0.41%
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: 3.47% Traditional cash on cash: 0.7% Airbnb Rental Income: $14576 Traditional Rental Income: $5155 Airbnb ROI: 3.47% 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.	$1,985,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 0.06% Airbnb Rental Income: $12355 Traditional Rental Income: $3415 Airbnb ROI: 3.69% Traditional ROI: 0.06%
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 \| 5,343 sq.ft.	$6,900,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.19% Airbnb Rental Income: $null Traditional Rental Income: $8952 Airbnb ROI: N/A Traditional ROI: 0.19%
207 Virginia Street Key West, FL Fantastic Old Town home located in the historic neighborhood of Bahama Village. Enjoy thi...	2 beds \| 2 baths \| 1,344 sq.ft.	$1,599,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 0.44% Airbnb Rental Income: $7991 Traditional Rental Income: $2851 Airbnb ROI: 2.88% Traditional ROI: 0.44%
58 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 8.46% Airbnb Rental Income: $7477 Traditional Rental Income: $5325 Airbnb ROI: 9.86% Traditional ROI: 8.46%
3312 Northside Drive #UNIT 302 Key West, FL Third Floor Unit Airy and Dry! 2 bedroom 2 full bath Largest floor plan available in the b...	2 beds \| 2 baths \| 792 sq.ft.	$485,000	Airbnb cash on cash: 9.35% Traditional cash on cash: 0.31% Airbnb Rental Income: $7477 Traditional Rental Income: $1940 Airbnb ROI: 9.35% Traditional ROI: 0.31%
709 Whitehead Street Key West, FL Welcome to this newly reimagined architectural gem in Old Town Key West. This historic hom...	4 beds \| 5 baths \| 1,801 sq.ft.	$3,750,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 0.33% Airbnb Rental Income: $15598 Traditional Rental Income: $5668 Airbnb ROI: 2.38% Traditional ROI: 0.33%
1438 Virginia Street Key West, FL Totally renovated home, currently set up as two units, one two bedroom, two bath and a one...	4 beds \| 3 baths \| 1,425 sq.ft.	$2,499,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 0.26% Airbnb Rental Income: $15439 Traditional Rental Income: $3839 Airbnb ROI: 4.08% Traditional ROI: 0.26%
2330 Staples Avenue Key West, FL This centrally located Key West property presents a rare opportunity for development, offe...	1 beds \| 1 baths \| 693 sq.ft.	$1,200,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 0.07% Airbnb Rental Income: $6856 Traditional Rental Income: $1752 Airbnb ROI: 3.45% Traditional ROI: 0.07%
923 Eaton Street Key West, FL Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic ho...	3 beds \| 2 baths \| 1,440 sq.ft.	$1,925,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 0.14% Airbnb Rental Income: $12355 Traditional Rental Income: $3270 Airbnb ROI: 3.96% Traditional ROI: 0.14%
2712 Harris Avenue Key West, FL Your Tropical Oasis awaits! Here is a fantastic opportunity to own an elevated home with ...	2 beds \| 2 baths \| 1,155 sq.ft.	$1,175,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 0.88% Airbnb Rental Income: $7477 Traditional Rental Income: $2449 Airbnb ROI: 4.16% Traditional ROI: 0.88%
1430 Thompson Street Key West, FL Welcome to your turn key dream home in Key West! This fully remodeled elevated, Conch styl...	3 beds \| 2 baths \| 1,644 sq.ft.	$1,950,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 0.47% Airbnb Rental Income: $12355 Traditional Rental Income: $3512 Airbnb ROI: 4.11% Traditional ROI: 0.47%
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.	$2,399,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 0.14% Airbnb Rental Income: $15439 Traditional Rental Income: $3909 Airbnb ROI: 4.07% Traditional ROI: 0.14%
3416 Flagler Avenue Key West, FL This Key West Conch house offers a perfect blend of island charm and modern updates.Spanni...	3 beds \| 3 baths \| 1,290 sq.ft.	$1,299,000	Airbnb cash on cash: 6.46% Traditional cash on cash: 1.45% Airbnb Rental Income: $11834 Traditional Rental Income: $3632 Airbnb ROI: 6.46% Traditional ROI: 1.45%
1709 Jamaica Drive Key West, FL Step from your boat into your Key West dream home! With 4-beds and 2-baths this concrete h...	4 beds \| 2 baths \| 1,652 sq.ft.	$1,795,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 0.75% Airbnb Rental Income: $14576 Traditional Rental Income: $3715 Airbnb ROI: 5.69% Traditional ROI: 0.75%
1610 Von Phister Street Key West, FL Beautifully renovated mid-century home in the heart of Key West. This property is sited on...	4 beds \| 4 baths \| 3,656 sq.ft.	$2,950,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 0.47% Airbnb Rental Income: $15439 Traditional Rental Income: $5293 Airbnb ROI: 3.17% Traditional ROI: 0.47%
1703 Seminary Street Key West, FL Tranquil Midtown Estate feels worlds away, while just minutes to delectable dining and nig...	4 beds \| 4 baths \| 2,812 sq.ft.	$3,199,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 0.27% Airbnb Rental Income: $15439 Traditional Rental Income: $5444 Airbnb ROI: 2.7% Traditional ROI: 0.27%
148 Golf Club Drive Key West, FL Welcome to your tropical retreat at the Key West Golf Club! This updated 2-bedroom, 1.5-ba...	2 beds \| 2 baths \| 810 sq.ft.	$699,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 0.33% Airbnb Rental Income: $7477 Traditional Rental Income: $1986 Airbnb ROI: 6.55% Traditional ROI: 0.33%
1519 Florida Street Key West, FL PRICED TO SELL. Discover Key West Quirk and versatility with this one-of-a-kind mid-centur...	9 beds \| 9 baths \| 4,037 sq.ft.	$3,199,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $7664 Airbnb ROI: N/A Traditional ROI: 0.84%
6810 Front Street #Snl13&B4sa Key West, FL This is a unique opportunity to own 1200 sq feet of beautifully renovated condo space alo...	2 beds \| 5 baths \| 1,200 sq.ft.	$1,600,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -1.26% Airbnb Rental Income: $7477 Traditional Rental Income: $4417 Airbnb ROI: -0.17% Traditional ROI: -1.26%
1221 Johnson Street Key West, FL Welcome to your tropical oasis in one of Key West's most coveted neighborhoods! This stunn...	4 beds \| 3 baths \| 2,360 sq.ft.	$3,350,000	Airbnb cash on cash: 2.43% Traditional cash on cash: -0.16% Airbnb Rental Income: $15439 Traditional Rental Income: $4638 Airbnb ROI: 2.43% Traditional ROI: -0.16%

Real Estate investment in Key-west, FL

There are 153 properties for sale in the city of Key West . The median list price in Key West is $1,637,500 and the average price per square foot is $925. In November 2024, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $3,592.

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

There are 153 investment properties available for sale in Key-west.

In 2024, the best neighborhood to buy investment property is Historic Seaport.

The ROI for Short-Term is higher than the Long-Term in Key-west with average rental income of $12,355.

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%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $7991

Traditional Rental Income: $2184

Airbnb ROI: 2%

Traditional ROI: -0.31%

2911 Venetian Drive

Key West, FL

3 beds | 3 baths | 1,925 sq.ft.

$1,500,000

Airbnb cash on cash: 5.66%

Traditional cash on cash: 1.77%

Airbnb Rental Income: $11834

Traditional Rental Income: $4255

Airbnb ROI: 5.66%

Traditional ROI: 1.77%

51 Sunset Key Drive

Key West, FL

3 beds | 3 baths | 1,920 sq.ft.

$3,695,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: -1.48%

Airbnb Rental Income: $12991

Traditional Rental Income: $3380

Airbnb ROI: 0.63%

Traditional ROI: -1.48%

1401 Simonton Street #UNIT 20

Key West, FL

2 beds | 2 baths | 907 sq.ft.

$1,200,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: -1.98%

Airbnb Rental Income: $7991

Traditional Rental Income: $2162

Airbnb ROI: 1.88%

Traditional ROI: -1.98%

63 Sunset Key Drive

Key West, FL

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

$2,400,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: -1.36%

Airbnb Rental Income: $7980

Traditional Rental Income: $3093

Airbnb ROI: 0.15%

Traditional ROI: -1.36%

1701 Patricia Street

Key West, FL

3 beds | 3 baths | 2,309 sq.ft.

$2,790,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 0.38%

Airbnb Rental Income: $12355

Traditional Rental Income: $4543

Airbnb ROI: 2.53%

Traditional ROI: 0.38%

1410 Reynolds Street

Key West, FL

3 beds | 3 baths | 2,262 sq.ft.

$3,999,999

Airbnb cash on cash: 1.06%

Traditional cash on cash: -0.48%

Airbnb Rental Income: $12355

Traditional Rental Income: $4415

Airbnb ROI: 1.06%

Traditional ROI: -0.48%

415 Amelia Street

Key West, FL

3 beds | 2 baths | 1,128 sq.ft.

$2,250,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $12355

Traditional Rental Income: $2854

Airbnb ROI: 3.28%