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
1119 Whitehead Street Key West, FL This stunning Old Town residence offers the perfect blend of historic charm and modern ele...	3 beds \| 2 baths \| 1,665 sq.ft.	$2,499,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 0.16% Airbnb Rental Income: $11712 Traditional Rental Income: $3920 Airbnb ROI: 2.6% Traditional ROI: 0.16%
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: 0.54% Traditional cash on cash: 1.17% Airbnb Rental Income: $3477 Traditional Rental Income: $3464 Airbnb ROI: 0.54% Traditional ROI: 1.17%
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%
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%
1420 White Street Key West, FL Stunning Grand Key West Historic Home Newly Renovated into a Gorgeous Single Family Home w...	5 beds \| 3 baths \| 2,608 sq.ft.	$3,299,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 0.26% Airbnb Rental Income: $16799 Traditional Rental Income: $5300 Airbnb ROI: 3.05% Traditional ROI: 0.26%
1800 Atlantic Boulevard #UNIT 337C Key West, FL Unit 337C at 1800 Atlantic is a beautifully furnished, turn key, two bedroom, two bath uni...	2 beds \| 2 baths \| 1,311 sq.ft.	$1,100,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.12% Airbnb Rental Income: $3408 Traditional Rental Income: $3543 Airbnb ROI: -0.99% Traditional ROI: -0.12%
816 Ashe Street Key West, FL NEW PRICE!! This beautifully renovated conch home is a proud recipient of the 2024 Histori...	3 beds \| 4 baths \| 1,522 sq.ft.	$2,150,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.04% Airbnb Rental Income: $2455 Traditional Rental Income: $4651 Airbnb ROI: -0.36% Traditional ROI: 1.04%
1320 Eliza Street Key West, FL Welcome to the School House on Eliza!1320 Eliza Street is a stunning corner-lot property t...	4 beds \| 4 baths \| 1,854 sq.ft.	$2,599,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 0.72% Airbnb Rental Income: $10782 Traditional Rental Income: $5196 Airbnb ROI: 2.21% Traditional ROI: 0.72%
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.	$2,100,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.67% Airbnb Rental Income: $11580 Traditional Rental Income: $5132 Airbnb ROI: 2.89% Traditional ROI: 0.67%
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.	$1,175,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 0.37% Airbnb Rental Income: $8333 Traditional Rental Income: $2543 Airbnb ROI: 4.22% Traditional ROI: 0.37%
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.	$1,325,000	Airbnb cash on cash: 5.11% Traditional cash on cash: 0.92% Airbnb Rental Income: $11088 Traditional Rental Income: $3894 Airbnb ROI: 5.11% Traditional ROI: 0.92%
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.	$895,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 1.21% Airbnb Rental Income: $7456 Traditional Rental Income: $2475 Airbnb ROI: 5.47% Traditional ROI: 1.21%
5603 College Road #UNIT D104 Key West, FL Enjoy one of the best priced waterfront properties in Key West. This stunning home is mov...	2 beds \| 2 baths \| 1,171 sq.ft.	$1,049,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 0.17% Airbnb Rental Income: $7456 Traditional Rental Income: $2835 Airbnb ROI: 3.44% 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.	$1,700,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 1.47% Airbnb Rental Income: $11580 Traditional Rental Income: $5193 Airbnb ROI: 4.17% Traditional ROI: 1.47%
243 Golf Club Drive Key West, FL MOTIVATED SELLERS Turn-key home with a history of rentals and a long term lease in place a...	3 beds \| 3 baths \| 1,600 sq.ft.	$1,330,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 0.99% Airbnb Rental Income: $11088 Traditional Rental Income: $3914 Airbnb ROI: 5.15% Traditional ROI: 0.99%
612 Mickens Lane Key West, FL Only 139 steps from the iconic Green Parrot (yes, we counted) and just 1.5 blocks off Duva...	2 beds \| 2 baths \| 823 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.	$1,795,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 0.38% Airbnb Rental Income: $9249 Traditional Rental Income: $3305 Airbnb ROI: 2.91% Traditional ROI: 0.38%
3312 Northside Drive #UNIT 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.	$350,000	Airbnb cash on cash: 7.38% Traditional cash on cash: 1.56% Airbnb Rental Income: $4857 Traditional Rental Income: $1946 Airbnb ROI: 7.38% Traditional ROI: 1.56%
1701 Atlantic Boulevard Key West, FL A stunning new renovation transforms this spacious elevated home to a total of 5bd/4ba plu...	5 beds \| 4 baths \| 2,703 sq.ft.	$2,599,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.19% Airbnb Rental Income: $null Traditional Rental Income: $6447 Airbnb ROI: N/A Traditional ROI: 1.19%
908 Catherine Street Key West, FL Motivated seller -- Quick Close! Welcome to 908 Catherine Street - a delightful blend of h...	3 beds \| 4 baths \| 1,572 sq.ft.	$1,799,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 2.67% Airbnb Rental Income: $11580 Traditional Rental Income: $6971 Airbnb ROI: 4.16% Traditional ROI: 2.67%
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.	$1,149,900	Airbnb cash on cash: 3.68% Traditional cash on cash: -0.41% Airbnb Rental Income: $8036 Traditional Rental Income: $2126 Airbnb ROI: 3.68% Traditional ROI: -0.41%
208 Golf Club Drive Key West, FL Welcome to Splendor @ Key West Golf Club, an impeccably transformed courtyard spa home loc...	2 beds \| 3 baths \| 1,120 sq.ft.	$995,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 1.11% Airbnb Rental Income: $7456 Traditional Rental Income: $3273 Airbnb ROI: 4.08% Traditional ROI: 1.11%
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.	$1,145,000	Airbnb cash on cash: 6.63% Traditional cash on cash: 0.42% Airbnb Rental Income: $11088 Traditional Rental Income: $2431 Airbnb ROI: 6.63% Traditional ROI: 0.42%
1705 Von Phister Street Key West, FL Welcome to one of Key West's most inviting neighborhoods, where tree-lined streets and a t...	3 beds \| 3 baths \| 1,284 sq.ft.	$1,245,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.21% Airbnb Rental Income: $2385 Traditional Rental Income: $3432 Airbnb ROI: -0.21% Traditional ROI: 1.21%
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%
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%
1525 Von Phister Street Key West, FL Elevated, fully renovated and perfectly located on one of Key West's most idyllic streets,...	3 beds \| 2 baths \| 1,434 sq.ft.	$1,899,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.46% Airbnb Rental Income: $2385 Traditional Rental Income: $3793 Airbnb ROI: -0.67% Traditional ROI: 0.46%
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: 0.64% Traditional cash on cash: 0.49% Airbnb Rental Income: $11896 Traditional Rental Income: $8952 Airbnb ROI: 0.64% 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 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: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $6647 Airbnb ROI: N/A Traditional ROI: 2.15%
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%
626 Margaret Street Key West, FL Welcome to this captivating historic Conch home, where the essence of Key West island luxu...	3 beds \| 2 baths \| 1,392 sq.ft.	$1,649,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 0.54% Airbnb Rental Income: $11712 Traditional Rental Income: $3626 Airbnb ROI: 4.42% Traditional ROI: 0.54%
312 Margaret Street Key West, FL Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful ho...	3 beds \| 3 baths \| 1,916 sq.ft.	$2,599,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 0.1% Airbnb Rental Income: $12364 Traditional Rental Income: $4621 Airbnb ROI: 2.38% Traditional ROI: 0.1%
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: 0.42% Traditional cash on cash: 0.83% Airbnb Rental Income: $3408 Traditional Rental Income: $2998 Airbnb ROI: 0.42% 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.	$999,999	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.01% Airbnb Rental Income: $2455 Traditional Rental Income: $3597 Airbnb ROI: 0.14% Traditional ROI: 2.01%

Real Estate investment in Key-west, FL

There are 182 properties for sale in the city of Key West . The median list price in Key West is $1,299,000 and the average price per square foot is $799. In November 2025, the average monthly cash on cash return in Key West is N/A%. The average monthly rental income in Key West is $3,112.

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

There are 182 investment properties available for sale in Key-west.

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

The ROI for Short-Term is higher than the Long-Term in Key-west with average rental income of $3,408.

Your search for investment property begins and ends here

Investment Property for Sale in Key West, FL

1119 Whitehead Street

Key West, FL

3 beds | 2 baths | 1,665 sq.ft.

$2,499,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $11712

Traditional Rental Income: $3920

Airbnb ROI: 2.6%

Traditional ROI: 0.16%

702 Florida Street

Key West, FL

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

$1,290,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $3477

Traditional Rental Income: $3464

Airbnb ROI: 0.54%

Traditional ROI: 1.17%

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%

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%

1420 White Street

Key West, FL

5 beds | 3 baths | 2,608 sq.ft.

$3,299,000

Airbnb cash on cash: 3.05%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $16799

Traditional Rental Income: $5300

Airbnb ROI: 3.05%

Traditional ROI: 0.26%

1800 Atlantic Boulevard #UNIT 337C

Key West, FL

2 beds | 2 baths | 1,311 sq.ft.

$1,100,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $3408

Traditional Rental Income: $3543

Airbnb ROI: -0.99%

Traditional ROI: -0.12%

816 Ashe Street

Key West, FL

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

$2,150,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $2455

Traditional Rental Income: $4651

Airbnb ROI: -0.36%

Traditional ROI: 1.04%

1320 Eliza Street

Key West, FL

4 beds | 4 baths | 1,854 sq.ft.

$2,599,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $10782

Traditional Rental Income: $5196

Airbnb ROI: 2.21%