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
85 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$459,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 10.33% Airbnb Rental Income: $3597 Traditional Rental Income: $5325 Airbnb ROI: 4.47% Traditional ROI: 10.33%
58 Golf Club Dr Key West, FL	2 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 8.46% Airbnb Rental Income: $3597 Traditional Rental Income: $5325 Airbnb ROI: 3.55% Traditional ROI: 8.46%
3301 Duck Avenue #D Key West, FL Key West New Town; 2 story townhouse; No HOA; 2 car garage; Laundry room. Living room down...	2 beds \| 2 baths \| 1,200 sq.ft.	$598,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 2.78% Airbnb Rental Income: $5824 Traditional Rental Income: $2979 Airbnb ROI: 5.37% Traditional ROI: 2.78%
1607 Sunshine Drive Key West, FL Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This n...	3 beds \| 3 baths \| 1,672 sq.ft.	$1,969,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 1.45% Airbnb Rental Income: $11827 Traditional Rental Income: $5163 Airbnb ROI: 3.91% Traditional ROI: 1.45%
1614 Washington St Key West, FL There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way ...	4 beds \| 10 baths \| 2,806 sq.ft.	$4,495,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.6% Airbnb Rental Income: $5911 Traditional Rental Income: $8519 Airbnb ROI: -0.31% Traditional ROI: 0.6%
1115 Fleming Street Key West, FL This rare Key West treasure hasn't changed hands in over a century, and it sits on the mos...	4 beds \| 2 baths \| 1,760 sq.ft.	$1,875,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.62% Airbnb Rental Income: $7690 Traditional Rental Income: $5932 Airbnb ROI: 1.78% Traditional ROI: 1.62%
1500 5th Street Key West, FL When value matters, this solid concrete New Town home stands apart with one of the most co...	4 beds \| 2 baths \| 2,111 sq.ft.	$979,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.56% Airbnb Rental Income: $5911 Traditional Rental Income: $4419 Airbnb ROI: 3.9% Traditional ROI: 3.56%
3201 Pearl Avenue Key West, FL Updated home in a prime central Key West location! Perfect for a local buyer or as an affo...	2 beds \| 2 baths \| 1,032 sq.ft.	$584,900	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.3% Airbnb Rental Income: $5824 Traditional Rental Income: $2823 Airbnb ROI: 6.53% Traditional ROI: 3.3%
1105 Olivia Street Key West, FL This elegant historic Old Town cottage is a rare offering paired with a highly competitive...	1 beds \| 1 baths \| 622 sq.ft.	$819,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 1.04% Airbnb Rental Income: $5797 Traditional Rental Income: $1985 Airbnb ROI: 4.21% Traditional ROI: 1.04%
817 Terry Lane Key West, FL One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of...	1 beds \| 1 baths \| 420 sq.ft.	$935,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 2% Airbnb Rental Income: $5429 Traditional Rental Income: $3425 Airbnb ROI: 2.98% Traditional ROI: 2%
611 Grinnell Street #4 Key West, FL Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3...	3 beds \| 2 baths \| 784 sq.ft.	$1,300,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 0.86% Airbnb Rental Income: $12642 Traditional Rental Income: $2998 Airbnb ROI: 6.94% Traditional ROI: 0.86%
710 Caroline Street Key West, FL Caroline Street, steps from the Historic Seaport. This is the Key West people picture befo...	4 beds \| 5 baths \| 2,250 sq.ft.	$3,495,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 0.53% Airbnb Rental Income: $7690 Traditional Rental Income: $6089 Airbnb ROI: 0.57% Traditional ROI: 0.53%
3365 Flagler Avenue Key West, FL Not your cookie-cutter Key West townhome! This thoughtfully updated 2-bedroom, 2-bath home...	2 beds \| 2 baths \| 1,339 sq.ft.	$860,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.11% Airbnb Rental Income: $5824 Traditional Rental Income: $4675 Airbnb ROI: 4.1% Traditional ROI: 4.11%
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: 2.31% Traditional cash on cash: 1.29% Airbnb Rental Income: $11137 Traditional Rental Income: $6602 Airbnb ROI: 2.31% Traditional ROI: 1.29%
3841 N Roosevelt Boulevard #632 Key West, FL Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includ...	2 beds \| 3 baths \| 1,357 sq.ft.	$749,000	Airbnb cash on cash: -3.29% Traditional cash on cash: -2.67% Airbnb Rental Income: $5824 Traditional Rental Income: $5097 Airbnb ROI: -3.29% Traditional ROI: -2.67%
719 Elizabeth Street Key West, FL Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Par...	3 beds \| 1 baths \| 943 sq.ft.	$1,196,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 1.97% Airbnb Rental Income: $12642 Traditional Rental Income: $4404 Airbnb ROI: 7.31% Traditional ROI: 1.97%
909 Grinnell Street Key West, FL Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's c...	7 beds \| 6 baths \| 2,790 sq.ft.	$1,899,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.35% Airbnb Rental Income: $7009 Traditional Rental Income: $9077 Airbnb ROI: 1.41% Traditional ROI: 3.35%
1405-1409 #ed Street Key West, FL Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently ...	3 beds \| 3 baths \| 1,872 sq.ft.	$2,790,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 1.14% Airbnb Rental Income: $11827 Traditional Rental Income: $6229 Airbnb ROI: 2.42% Traditional ROI: 1.14%
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: 2.39% Traditional cash on cash: 0.42% Airbnb Rental Income: $10441 Traditional Rental Income: $4412 Airbnb ROI: 2.39% 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: 5.54% Traditional cash on cash: 3.24% Airbnb Rental Income: $8317 Traditional Rental Income: $4613 Airbnb ROI: 5.54% Traditional ROI: 3.24%
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: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $8144 Airbnb ROI: N/A Traditional ROI: 2.97%
711 Galveston Lane Key West, FL Nestled down a private and picturesque lane, this charming conch-style cottage offers the ...	3 beds \| 2 baths \| 866 sq.ft.	$1,195,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 2.39% Airbnb Rental Income: $12642 Traditional Rental Income: $4639 Airbnb ROI: 7.52% Traditional ROI: 2.39%
S 3930 Roosevelt Boulevard #S303 Key West, FL Looking for a move-in condo in Key West that's high and dry, close to the airport and on t...	3 beds \| 2 baths \| 1,069 sq.ft.	$599,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.5% Airbnb Rental Income: $6800 Traditional Rental Income: $4326 Airbnb ROI: 6.56% Traditional ROI: 4.5%
1113 Stump Lane Key West, FL Experience the ideal blend of historic charm and modern luxury in this fully renovated and...	4 beds \| 5 baths \| 2,985 sq.ft.	$4,450,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.19% Airbnb Rental Income: $15808 Traditional Rental Income: $10125 Airbnb ROI: 1.89% Traditional ROI: 1.19%
405 Petronia Street Key West, FL Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/...	N/A beds \| 4 baths \| 1,596 sq.ft.	$2,999,999	Airbnb cash on cash: 0.44% Traditional cash on cash: 0.63% Airbnb Rental Income: $5842 Traditional Rental Income: $5224 Airbnb ROI: 0.44% Traditional ROI: 0.63%
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: -0.6% Traditional cash on cash: -1.09% Airbnb Rental Income: $5824 Traditional Rental Income: $3781 Airbnb ROI: -0.6% 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: -0.6% Traditional cash on cash: -1.08% Airbnb Rental Income: $5824 Traditional Rental Income: $3781 Airbnb ROI: -0.6% Traditional ROI: -1.08%
1719 Laird Street Key West, FL Key West Pool Home on a Double Lot -- 4 Bedroom, 3 Bathroom CBS, Parking for 4 ALL THE...	4 beds \| 3 baths \| 2,276 sq.ft.	$1,850,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.09% Airbnb Rental Income: $5911 Traditional Rental Income: $7617 Airbnb ROI: 1.41% Traditional ROI: 3.09%
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: 1.46% Traditional cash on cash: 0.24% Airbnb Rental Income: $8293 Traditional Rental Income: $4797 Airbnb ROI: 1.46% Traditional ROI: 0.24%
103 Front Street Key West, FL 103 Front Street is a one of a kind masterpiece of architectural design and modern aesthet...	3 beds \| 3 baths \| 3,000 sq.ft.	$6,850,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -0.8% Airbnb Rental Income: $10441 Traditional Rental Income: $8263 Airbnb ROI: -0.77% Traditional ROI: -0.8%
1505 Johnson Street Key West, FL POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This ...	3 beds \| 3 baths \| 1,489 sq.ft.	$1,474,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 2.75% Airbnb Rental Income: $9339 Traditional Rental Income: $5897 Airbnb ROI: 3.99% Traditional ROI: 2.75%
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.	$940,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 1.88% Airbnb Rental Income: $5824 Traditional Rental Income: $4150 Airbnb ROI: 2.46% Traditional ROI: 1.88%
738 Olivia Street Key West, FL Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully r...	1 beds \| 2 baths \| 767 sq.ft.	$1,100,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.26% Airbnb Rental Income: $5797 Traditional Rental Income: $3710 Airbnb ROI: 3.17% Traditional ROI: 2.26%
48 Merganser Lane Key West, FL An easier way to own in Key West. This 2-bedroom, 1.5-bath townhome in the Key West Golf C...	2 beds \| 2 baths \| 780 sq.ft.	$619,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.68% Airbnb Rental Income: $5824 Traditional Rental Income: $3883 Airbnb ROI: 4.99% Traditional ROI: 3.68%
2613 Gulfview Drive Key West, FL Rare WATERFRONT home on the island of Key West, an incredible value priced well below the ...	3 beds \| 3 baths \| 1,320 sq.ft.	$1,549,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.22% Airbnb Rental Income: $6800 Traditional Rental Income: $4675 Airbnb ROI: 1.78% Traditional ROI: 1.22%
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: 3.41% Traditional cash on cash: 1.89% Airbnb Rental Income: $5440 Traditional Rental Income: $3357 Airbnb ROI: 3.41% Traditional ROI: 1.89%
815 Pearl Street #2 Key West, FL A little Key West retreat with a lot to love. Tucked away in the highly desirable Meadows ...	1 beds \| 1 baths \| 546 sq.ft.	$575,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 4.42% Airbnb Rental Income: $5440 Traditional Rental Income: $3431 Airbnb ROI: 6.12% 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: 3.01% Traditional cash on cash: 0.98% Airbnb Rental Income: $9339 Traditional Rental Income: $4915 Airbnb ROI: 3.01% Traditional ROI: 0.98%
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: 8.52% Traditional cash on cash: 1.51% Airbnb Rental Income: $9505 Traditional Rental Income: $2512 Airbnb ROI: 8.52% 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: -1.7% Traditional cash on cash: 2.78% Airbnb Rental Income: $1427 Traditional Rental Income: $3615 Airbnb ROI: -1.7% Traditional ROI: 2.78%

Real Estate investment in Key-west, FL

There are 177 properties for sale in the city of Key West . The median list price in Key West is $1,271,739 and the average price per square foot is $820. In September 2026, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $3,077.

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

There are 177 investment properties available for sale in Key-west.

In 2026, the best neighborhood to buy investment property is Truman Annex.

The ROI for Short-Term is higher than the Long-Term in Key-west with average rental income of $9,037.

Your search for investment property begins and ends here

Investment Property for Sale in Key West, FL

85 Golf Club Dr

Key West, FL

2 beds | 3 baths | N/A

$459,000

Airbnb cash on cash: 4.47%

Traditional cash on cash: 10.33%

Airbnb Rental Income: $3597

Traditional Rental Income: $5325

Airbnb ROI: 4.47%

Traditional ROI: 10.33%

58 Golf Club Dr

Key West, FL

2 beds | 3 baths | N/A

$549,000

Airbnb cash on cash: 3.55%

Traditional cash on cash: 8.46%

Airbnb Rental Income: $3597

Traditional Rental Income: $5325

Airbnb ROI: 3.55%

Traditional ROI: 8.46%

3301 Duck Avenue #D

Key West, FL

2 beds | 2 baths | 1,200 sq.ft.

$598,000

Airbnb cash on cash: 5.37%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $5824

Traditional Rental Income: $2979

Airbnb ROI: 5.37%

Traditional ROI: 2.78%

1607 Sunshine Drive

Key West, FL

3 beds | 3 baths | 1,672 sq.ft.

$1,969,000

Airbnb cash on cash: 3.91%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $11827

Traditional Rental Income: $5163

Airbnb ROI: 3.91%

Traditional ROI: 1.45%

1614 Washington St

Key West, FL

4 beds | 10 baths | 2,806 sq.ft.

$4,495,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $5911

Traditional Rental Income: $8519

Airbnb ROI: -0.31%

Traditional ROI: 0.6%

1115 Fleming Street

Key West, FL

4 beds | 2 baths | 1,760 sq.ft.

$1,875,000

Airbnb cash on cash: 1.78%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $7690

Traditional Rental Income: $5932

Airbnb ROI: 1.78%

Traditional ROI: 1.62%

1500 5th Street

Key West, FL

4 beds | 2 baths | 2,111 sq.ft.

$979,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $5911

Traditional Rental Income: $4419

Airbnb ROI: 3.9%

Traditional ROI: 3.56%

3201 Pearl Avenue

Key West, FL

2 beds | 2 baths | 1,032 sq.ft.

$584,900

Airbnb cash on cash: 6.53%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $5824

Traditional Rental Income: $2823

Airbnb ROI: 6.53%