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 43 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
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%
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%
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%
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%
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%
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%
2601 S Roosevelt Boulevard #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.	$950,000	Airbnb cash on cash: 4% Traditional cash on cash: 1.88% Airbnb Rental Income: $7456 Traditional Rental Income: $4150 Airbnb ROI: 4% Traditional ROI: 1.88%
1800 Atlantic Boulevard #308A Key West, FL Discover coastal living at 1800 Atlantic with a spacious two-bedroom, two-bath residence o...	2 beds \| 2 baths \| 1,316 sq.ft.	$899,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.29% Airbnb Rental Income: $3408 Traditional Rental Income: $4898 Airbnb ROI: -0.39% Traditional ROI: 2.29%
817 Eaton Street #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.	$820,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 1.97% Airbnb Rental Income: $6609 Traditional Rental Income: $3737 Airbnb ROI: 4.04% Traditional ROI: 1.97%
1203 Newton Street #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: 4.39% Traditional cash on cash: 1.89% Airbnb Rental Income: $6205 Traditional Rental Income: $3357 Airbnb ROI: 4.39% Traditional ROI: 1.89%
815 Pearl Street #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.	$575,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 4.42% Airbnb Rental Income: $6205 Traditional Rental Income: $3431 Airbnb ROI: 7.31% Traditional ROI: 4.42%
1901 S Roosevelt Boulevard #401E Key West, FL Discover the rare opportunity to own a premier developer's unit in one of Key West's most ...	3 beds \| 2 baths \| 1,395 sq.ft.	$1,425,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.98% Airbnb Rental Income: $2385 Traditional Rental Income: $4915 Airbnb ROI: -1.37% Traditional ROI: 0.98%
816 South Street #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.	$599,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 3.86% Airbnb Rental Income: $6590 Traditional Rental Income: $3403 Airbnb ROI: 7.26% Traditional ROI: 3.86%
1014 Truman Avenue #202 Key West, FL 1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West...	2 beds \| 2 baths \| 1,017 sq.ft.	$799,900	Airbnb cash on cash: 7.2% Traditional cash on cash: 1.51% Airbnb Rental Income: $8333 Traditional Rental Income: $2512 Airbnb ROI: 7.2% Traditional ROI: 1.51%
2601 S Roosevelt Boulevard #204A Key West, FL Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath resid...	1 beds \| 1 baths \| 754 sq.ft.	$625,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 2.78% Airbnb Rental Income: $4857 Traditional Rental Income: $3615 Airbnb ROI: 3.2% Traditional ROI: 2.78%
927 Thomas Street #2 Key West, FL This show-stopping luxury condo delivers a rare blend of historic charm with a fully renov...	2 beds \| 2 baths \| 1,205 sq.ft.	$1,275,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 1.4% Airbnb Rental Income: $6658 Traditional Rental Income: $4587 Airbnb ROI: 2.05% Traditional ROI: 1.4%
927 Thomas Street #4 Key West, FL Located in one of Key West's newer developments at The Captains House in Bahama Village, t...	2 beds \| 1 baths \| 762 sq.ft.	$859,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.98% Airbnb Rental Income: $6658 Traditional Rental Income: $3944 Airbnb ROI: 3.75% Traditional ROI: 1.98%
1075 Duval Street #R10 Key West, FL Tucked away in the heart of Old-Town Key West! Welcome to 1075 R10 Duval Street offers the...	2 beds \| 3 baths \| 1,240 sq.ft.	$1,150,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 0.98% Airbnb Rental Income: $8279 Traditional Rental Income: $4534 Airbnb ROI: 3.01% Traditional ROI: 0.98%
2601 S Roosevelt Boulevard #223C Key West, FL Well maintained 2BD/2BA condo that was converted from a 3BD for extra living space. Offeri...	2 beds \| 2 baths \| 1,221 sq.ft.	$849,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 5.05% Airbnb Rental Income: $3408 Traditional Rental Income: $5423 Airbnb ROI: 1.55% Traditional ROI: 5.05%
617 Fleming Street #Apt 4 Key West, FL An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! ...	2 beds \| 2 baths \| 1,020 sq.ft.	$1,175,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 0.97% Airbnb Rental Income: $8036 Traditional Rental Income: $4504 Airbnb ROI: 2.81% Traditional ROI: 0.97%
3675 Seaside Drive #342 Key West, FL Welcome to your private slice of paradise at 3675 Seaside Drive, Unit 342 -- a highly desi...	2 beds \| 2 baths \| 772 sq.ft.	$599,000	Airbnb cash on cash: 7.45% Traditional cash on cash: 4.06% Airbnb Rental Income: $7456 Traditional Rental Income: $4132 Airbnb ROI: 7.45% Traditional ROI: 4.06%
3841 N Roosevelt Boulevard #121 Key West, FL Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of BEACHFRONT living at the Ke...	1 beds \| 2 baths \| 814 sq.ft.	$799,000	Airbnb cash on cash: -3% Traditional cash on cash: -2.9% Airbnb Rental Income: $4857 Traditional Rental Income: $3932 Airbnb ROI: -3% Traditional ROI: -2.9%
3625 Seaside Drive #25304 Key West, FL Enjoy the view of the Salt Ponds & catch sunset from the balcony of this 2 bedroom / 2 bat...	2 beds \| 2 baths \| 798 sq.ft.	$899,995	Airbnb cash on cash: 3.55% Traditional cash on cash: -0.8% Airbnb Rental Income: $7456 Traditional Rental Income: $2385 Airbnb ROI: 3.55% Traditional ROI: -0.8%
3312 Northside Drive #205 Key West, FL Charming second-floor 1 bedroom, 1 bath condominium featuring a functional layout with a k...	1 beds \| 1 baths \| 528 sq.ft.	$344,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 5.77% Airbnb Rental Income: $4857 Traditional Rental Income: $3363 Airbnb ROI: 7.3% Traditional ROI: 5.77%
115 Front Street #Apt 102 Key West, FL HARBOUR PLACE \| TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views f...	2 beds \| 2 baths \| 1,260 sq.ft.	$1,100,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 2.34% Airbnb Rental Income: $8036 Traditional Rental Income: $4898 Airbnb ROI: 3.92% Traditional ROI: 2.34%
3312 Northside Drive #Apt 712 Key West, FL Experience Key West sunsets and ocean breezes from this TOP-FLOOR unit! This one-bedroom, ...	1 beds \| 1 baths \| 528 sq.ft.	$345,000	Airbnb cash on cash: 7.4% Traditional cash on cash: 6.18% Airbnb Rental Income: $4857 Traditional Rental Income: $3463 Airbnb ROI: 7.4% Traditional ROI: 6.18%
800 Fleming Street #C1 Key West, FL Discover a rare blend of history, artistry, and luxury in this extraordinary residence at ...	2 beds \| 3 baths \| 1,550 sq.ft.	$2,495,000	Airbnb cash on cash: 0.84% Traditional cash on cash: -0.4% Airbnb Rental Income: $8261 Traditional Rental Income: $3828 Airbnb ROI: 0.84% Traditional ROI: -0.4%
1800 Atlantic Boulevard #427C Key West, FL This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean v...	2 beds \| 2 baths \| 1,311 sq.ft.	$1,025,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 1.82% Airbnb Rental Income: $3408 Traditional Rental Income: $3558 Airbnb ROI: 0.86% Traditional ROI: 1.82%
2601 S Roosevelt Boulevard #Apt 103C Key West, FL Thoughtfully reimagined from its deeded 3-bedroom layout into a spacious 2-bedroom, 2-bath...	3 beds \| 2 baths \| 1,221 sq.ft.	$899,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.29% Airbnb Rental Income: $2385 Traditional Rental Income: $3404 Airbnb ROI: -0.62% Traditional ROI: 1.29%
620 Thomas Street #186 Key West, FL Located in the desirable Truman Annex Shipyard community, this beautifully updated first-f...	2 beds \| 1 baths \| 680 sq.ft.	$939,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.41% Airbnb Rental Income: $8036 Traditional Rental Income: $3664 Airbnb ROI: 5.66% Traditional ROI: 2.41%
1901 S Roosevelt Boulevard #401S Key West, FL Full ocean view - top floor unit! Presumably the best view in the preferred South Wing of ...	2 beds \| 2 baths \| 1,099 sq.ft.	$990,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 1.12% Airbnb Rental Income: $3408 Traditional Rental Income: $2695 Airbnb ROI: 1.08% Traditional ROI: 1.12%
1800 Atlantic Boulevard #315B Key West, FL TRANSIENT investment opportunity awaits. Spacious 2bd/2ba situated in the centrally locate...	2 beds \| 2 baths \| 1,469 sq.ft.	$1,849,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.69% Airbnb Rental Income: $3408 Traditional Rental Income: $3886 Airbnb ROI: -0.03% Traditional ROI: 0.69%
204 Southard Street #5 Key West, FL Freshly relaunched and ready for its next chapter, this beautifully maintained 2-bedroom, ...	2 beds \| 1 baths \| 646 sq.ft.	$865,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 0.37% Airbnb Rental Income: $8036 Traditional Rental Income: $1734 Airbnb ROI: 6.29% Traditional ROI: 0.37%
6810 Front Street #Snl13&B4sa Key West, FL This is a unique opportunity to own 1200 sq feet of beautifully renovated condo space alon...	2 beds \| 5 baths \| 1,200 sq.ft.	$1,000,000	Airbnb cash on cash: 0.3% Traditional cash on cash: -0.27% Airbnb Rental Income: $7456 Traditional Rental Income: $5488 Airbnb ROI: 0.3% Traditional ROI: -0.27%
1011 Simonton Street #1 Key West, FL Excellent opportunity whether looking for a private residence or an investment. This condo...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,799,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 1.32% Airbnb Rental Income: $11712 Traditional Rental Income: $5329 Airbnb ROI: 3.85% Traditional ROI: 1.32%

Your search for investment property begins and ends here

Condos for Sale in Key West, FL

3841 N Roosevelt Boulevard #213

Key West, FL

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

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%

115 Front Street #101

Key West, FL

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%

1209 Truman Avenue #5

Key West, FL

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%

3841 N Roosevelt Boulevard #332

Key West, FL

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

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%

1800 Atlantic Boulevard #327C

Key West, FL

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%

422 Amelia Street #L6

Key West, FL

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%