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.

Condos for Sale in Key West, FL

Search for Condo for Sale in Key West, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 50 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1401 Simonton Street #UNIT 20 Key West, FL Santa Maria Suites Old Town Key West TRANSIENT LICENSED 2BR CONDO! One of the most luxurio...	2 beds \| 3 baths \| 907 sq.ft.	$875,000	Airbnb cash on cash: 2.21% Traditional cash on cash: -3.38% Airbnb Rental Income: $8279 Traditional Rental Income: $2162 Airbnb ROI: 2.21% Traditional ROI: -3.38%
816 South Street #UNIT 4 Key West, FL Experience the charm of this bright and airy 1-bedroom, 1-bathroom Southpark Condominium l...	1 beds \| 1 baths \| 640 sq.ft.	$629,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 1.31% Airbnb Rental Income: $6590 Traditional Rental Income: $2039 Airbnb ROI: 6.87% Traditional ROI: 1.31%
3625 Seaside Drive #UNIT 25105 Key West, FL Transient Nightly Rental Just Listed! Come invest into Key West nightly vacation rentals w...	2 beds \| 2 baths \| 798 sq.ft.	$870,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 1.27% Airbnb Rental Income: $7456 Traditional Rental Income: $2475 Airbnb ROI: 5.65% Traditional ROI: 1.27%
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%
1500 Atlantic Boulevard #UNIT 311 Key West, FL If you have been waiting for an oceanfront condo that actually feels turnkey, Unit 311 at ...	2 beds \| 2 baths \| 1,531 sq.ft.	$1,899,999	Airbnb cash on cash: -1.97% Traditional cash on cash: -0.5% Airbnb Rental Income: $3408 Traditional Rental Income: $5247 Airbnb ROI: -1.97% Traditional ROI: -0.5%
2601 S Roosevelt Boulevard #UNIT 103C Key West, FL Experience resort-style living in beautiful Key West. This upgraded condominium is located...	2 beds \| 2 baths \| 1,221 sq.ft.	$899,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.86% Airbnb Rental Income: $3408 Traditional Rental Income: $2998 Airbnb ROI: 0.45% Traditional ROI: 0.86%
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 \| 1 baths \| 836 sq.ft.	$679,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.81% Airbnb Rental Income: $2214 Traditional Rental Income: $2356 Airbnb ROI: -0.3% Traditional ROI: 0.81%
201 Coppitt Rd #103B Key West, FL This Waterfront low maintanence condo has everything you'd want for either your primary re...	1 beds \| 1 baths \| 536 sq.ft.	$329,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 0.51% Airbnb Rental Income: $1693 Traditional Rental Income: $1841 Airbnb ROI: -1.49% Traditional ROI: 0.51%
1901 S Roosevelt Boulevard 307W Key West, FL Beach lovers delight at La Brisa! Third floor, picturesque views of the Key West Salt Pond...	2 beds \| 2 baths \| 1,099 sq.ft.	$745,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 2.44% Airbnb Rental Income: $3408 Traditional Rental Income: $3122 Airbnb ROI: 1.76% Traditional ROI: 2.44%
800 Fleming Street #UNIT B-3 Key West, FL Perfectly situated just three blocks from Duval Street and two from the grocery store, thi...	2 beds \| 2 baths \| 1,207 sq.ft.	$1,499,999	Airbnb cash on cash: 3.12% Traditional cash on cash: 0.56% Airbnb Rental Income: $8261 Traditional Rental Income: $3123 Airbnb ROI: 3.12% Traditional ROI: 0.56%
1901 S Roosevelt Boulevard #UNIT 407W Key West, FL Welcome to this exquisite two-bedroom, two-bathroom penthouse condo in the gated community...	2 beds \| 2 baths \| 1,099 sq.ft.	$849,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 1.48% Airbnb Rental Income: $3408 Traditional Rental Income: $2783 Airbnb ROI: 1.32% Traditional ROI: 1.48%
817 Eaton Street #UNIT 1 Key West, FL Old Town Condo Near Duval:Bright 1-bedroom, 1-bath condo located in the heart of Historic ...	1 beds \| 1 baths \| 740 sq.ft.	$850,000	Airbnb cash on cash: 3.86% Traditional cash on cash: -0.2% Airbnb Rental Income: $6609 Traditional Rental Income: $2102 Airbnb ROI: 3.86% Traditional ROI: -0.2%
1901 S Roosevelt Boulevard #UNIT 104N Key West, FL Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in t...	2 beds \| 2 baths \| 1,176 sq.ft.	$875,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.35% Airbnb Rental Income: $3408 Traditional Rental Income: $4306 Airbnb ROI: 1.32% Traditional ROI: 3.35%
815 Pearl Street #UNIT 2 Key West, FL Quaint Key West Condominium - Discover 815 Pearl Street Unit 2, a charming 1-bedroom, 1-ba...	1 beds \| 1 baths \| 546 sq.ft.	$675,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 0.96% Airbnb Rental Income: $2214 Traditional Rental Income: $1754 Airbnb ROI: 0.8% Traditional ROI: 0.96%
1203 Newton Street #UNIT 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: -0.72% Traditional cash on cash: -0.3% Airbnb Rental Income: $2214 Traditional Rental Income: $1927 Airbnb ROI: -0.72% Traditional ROI: -0.3%
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: -2.14% Airbnb Rental Income: $7456 Traditional Rental Income: $3560 Airbnb ROI: -0.78% Traditional ROI: -2.14%
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: -2.13% Airbnb Rental Income: $7456 Traditional Rental Income: $3560 Airbnb ROI: -0.77% Traditional ROI: -2.13%
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: -2.96% Airbnb Rental Income: $7456 Traditional Rental Income: $3948 Airbnb ROI: -0.48% Traditional ROI: -2.96%
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: -2.28% Airbnb Rental Income: $11088 Traditional Rental Income: $4402 Airbnb ROI: 2.73% Traditional ROI: -2.28%
2601 S Roosevelt Boulevard #UNIT 107B Key West, FL Discover resort-style living at Key West By The Sea! This ground-floor 1BR/1BA condo featu...	1 beds \| 1 baths \| 754 sq.ft.	$615,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 2.28% Airbnb Rental Income: $4857 Traditional Rental Income: $2084 Airbnb ROI: 5.37% Traditional ROI: 2.28%
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: 0.16% Airbnb Rental Income: $12364 Traditional Rental Income: $3869 Airbnb ROI: 3.15% Traditional ROI: 0.16%
1830 Fogarty Avenue #UNIT 4 Key West, FL Privately situated at the rear of a boutique seven-unit complex, this bright 1BD/1BA Key W...	1 beds \| 1 baths \| 388 sq.ft.	$445,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.2% Airbnb Rental Income: $2797 Traditional Rental Income: $1862 Airbnb ROI: 1.87% Traditional ROI: 1.2%
204 Southard Street #UNIT 5 Key West, FL Welcome to your perfect island retreat! This beautifully maintained 2-bedroom, 1-bathroom ...	2 beds \| 1 baths \| 646 sq.ft.	$869,000	Airbnb cash on cash: 5.05% Traditional cash on cash: -0.88% Airbnb Rental Income: $8036 Traditional Rental Income: $1706 Airbnb ROI: 5.05% Traditional ROI: -0.88%
3635 Seaside Drive #UNIT 314 Key West, FL CATCH THE SUNSET every day from your third floor private balcony in this beautifully maint...	2 beds \| 2 baths \| 772 sq.ft.	$528,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 1.11% Airbnb Rental Income: $7456 Traditional Rental Income: $2518 Airbnb ROI: 8.21% Traditional ROI: 1.11%
1124 Catherine Street #UNIT 201 Key West, FL Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo b...	1 beds \| 1 baths \| 454 sq.ft.	$449,000	Airbnb cash on cash: 7.1% Traditional cash on cash: -1.25% Airbnb Rental Income: $6712 Traditional Rental Income: $1897 Airbnb ROI: 7.1% Traditional ROI: -1.25%
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.	$649,000	Airbnb cash on cash: 8% Traditional cash on cash: -0.74% Airbnb Rental Income: $9324 Traditional Rental Income: $2286 Airbnb ROI: 8% Traditional ROI: -0.74%
413 Emma Street #UNIT A Key West, FL Welcome to 413 Emma Street, Unit A - a rare opportunity to own a piece of Key West history...	2 beds \| 3 baths \| 1,418 sq.ft.	$2,250,000	Airbnb cash on cash: 0.55% Traditional cash on cash: -1.22% Airbnb Rental Income: $8036 Traditional Rental Income: $2814 Airbnb ROI: 0.55% Traditional ROI: -1.22%
2601 S Roosevelt Boulevard #UNIT 319C Key West, FL New Price!! Key West By The Sea offers the quintessential beach condominium lifestyle. Th...	1 beds \| 1 baths \| 754 sq.ft.	$596,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 0.74% Airbnb Rental Income: $2797 Traditional Rental Income: $2073 Airbnb ROI: 0.86% Traditional ROI: 0.74%
5601 College Road #UNIT A201 Key West, FL Welcome to Sunset Marina, a prestigious gated condominium community known for its breathta...	2 beds \| 2 baths \| 1,558 sq.ft.	$1,290,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 0.38% Airbnb Rental Income: $7456 Traditional Rental Income: $4341 Airbnb ROI: 1.78% Traditional ROI: 0.38%
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.	$1,124,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 1.38% Airbnb Rental Income: $3477 Traditional Rental Income: $3179 Airbnb ROI: 0.93% Traditional ROI: 1.38%
3625 Seaside Drive #UNIT 25204 Key West, FL Attention Investors - Key West Transient License Condo! Own a nightly vacation rental cond...	2 beds \| 2 baths \| 798 sq.ft.	$925,000	Airbnb cash on cash: 3.55% Traditional cash on cash: -0.48% Airbnb Rental Income: $7456 Traditional Rental Income: $2550 Airbnb ROI: 3.55% Traditional ROI: -0.48%
3312 Northside Drive #UNIT 512 Key West, FL Investor special! Current renter can keep the Condo paid until you are ready to occupy. Be...	1 beds \| 1 baths \| 528 sq.ft.	$393,900	Airbnb cash on cash: 8.55% Traditional cash on cash: 3.42% Airbnb Rental Income: $4857 Traditional Rental Income: $1964 Airbnb ROI: 8.55% Traditional ROI: 3.42%
1800 Atlantic Boulevard #UNIT 327C Key West, FL Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at on...	2 beds \| 2 baths \| 1,311 sq.ft.	$1,700,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.55% Airbnb Rental Income: $3408 Traditional Rental Income: $3542 Airbnb ROI: -1.12% Traditional ROI: -0.55%
422 Amelia Street #UNIT 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.	$1,450,000	Airbnb cash on cash: 2.48% Traditional cash on cash: -0.04% Airbnb Rental Income: $6609 Traditional Rental Income: $1923 Airbnb ROI: 2.48% Traditional ROI: -0.04%
620 Thomas Street #UNIT 175 Key West, FL This fully furnished first-floor end unit in Shipyard offers comfort, style, and an unbeat...	2 beds \| 1 baths \| 604 sq.ft.	$799,000	Airbnb cash on cash: 5.45% Traditional cash on cash: -0.94% Airbnb Rental Income: $8036 Traditional Rental Income: $1752 Airbnb ROI: 5.45% Traditional ROI: -0.94%
1901 S Roosevelt Boulevard #UNIT 208E Key West, FL Rare Direct Oceanview 3BD/2BA Condominium located in The La Brisa community. This condo of...	3 beds \| 2 baths \| 1,395 sq.ft.	$1,495,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.31% Airbnb Rental Income: $2385 Traditional Rental Income: $3815 Airbnb ROI: -1.14% Traditional ROI: 0.31%
2601 S Roosevelt Boulevard #UNIT 406A Key West, FL Spectacular sunrise ocean views from this beautifully renovated Key West By The Sea condo ...	2 beds \| 2 baths \| 980 sq.ft.	$1,095,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 0.36% Airbnb Rental Income: $7456 Traditional Rental Income: $2990 Airbnb ROI: 3.34% Traditional ROI: 0.36%
5960 Peninsular Ave #110 Key West, FL Wake up to panoramic Atlantic Ocean views from this 2 bedroom, 2 bathroom condo in Oceansi...	2 beds \| 2 baths \| 1,352 sq.ft.	$1,550,000	Airbnb cash on cash: 1.31% Traditional cash on cash: -1.1% Airbnb Rental Income: $7839 Traditional Rental Income: $2875 Airbnb ROI: 1.31% Traditional ROI: -1.1%
1616 Atlantic Boulevard #UNIT 3 Key West, FL OFFERED FULLY FURNISHED and completely renovated, this is the townhome buyers wait for and...	2 beds \| 3 baths \| 1,940 sq.ft.	$1,599,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.08% Airbnb Rental Income: $3408 Traditional Rental Income: $4772 Airbnb ROI: -0.35% Traditional ROI: 1.08%
120 Angela Street #UNIT 102 Key West, FL Welcome to Old Key West luxury living in this beautifully appointed 2-bedroom, 2-bathroom ...	2 beds \| 2 baths \| 852 sq.ft.	$995,000	Airbnb cash on cash: 4.32% Traditional cash on cash: -0.5% Airbnb Rental Income: $8036 Traditional Rental Income: $2044 Airbnb ROI: 4.32% Traditional ROI: -0.5%

Your search for investment property begins and ends here

Condos for Sale in Key West, FL

1401 Simonton Street #UNIT 20

Key West, FL

2 beds | 3 baths | 907 sq.ft.

$875,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: -3.38%

Airbnb Rental Income: $8279

Traditional Rental Income: $2162

Airbnb ROI: 2.21%

Traditional ROI: -3.38%

816 South Street #UNIT 4

Key West, FL

1 beds | 1 baths | 640 sq.ft.

$629,000

Airbnb cash on cash: 6.87%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $6590

Traditional Rental Income: $2039

Airbnb ROI: 6.87%

Traditional ROI: 1.31%

3625 Seaside Drive #UNIT 25105

Key West, FL

2 beds | 2 baths | 798 sq.ft.

$870,000

Airbnb cash on cash: 5.65%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $7456

Traditional Rental Income: $2475

Airbnb ROI: 5.65%

Traditional ROI: 1.27%

1011 Simonton Street #1

Key West, FL

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%

1500 Atlantic Boulevard #UNIT 311

Key West, FL

2 beds | 2 baths | 1,531 sq.ft.

$1,899,999

Airbnb cash on cash: -1.97%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $3408

Traditional Rental Income: $5247

Airbnb ROI: -1.97%

Traditional ROI: -0.5%

2601 S Roosevelt Boulevard #UNIT 103C

Key West, FL

2 beds | 2 baths | 1,221 sq.ft.

$899,000

Airbnb cash on cash: 0.45%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $3408

Traditional Rental Income: $2998

Airbnb ROI: 0.45%

Traditional ROI: 0.86%

1209 Truman Avenue #UNIT 2

Key West, FL

1 beds | 1 baths | 836 sq.ft.

$679,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 0.81%

Airbnb Rental Income: $2214

Traditional Rental Income: $2356

Airbnb ROI: -0.3%

Traditional ROI: 0.81%

201 Coppitt Rd #103B

Key West, FL

1 beds | 1 baths | 536 sq.ft.

$329,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $1693

Traditional Rental Income: $1841

Airbnb ROI: -1.49%