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.	$2,250,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 1.03% Airbnb Rental Income: $11712 Traditional Rental Income: $5529 Airbnb ROI: 2.97% Traditional ROI: 1.03%
224 Golf Club Drive Key West, FL Stylish ''Spa'' home within the enclave of The Sanctuary of the Key West Golf Club. An op...	2 beds \| 3 baths \| 1,120 sq.ft.	$875,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 4.27% Airbnb Rental Income: $7456 Traditional Rental Income: $5046 Airbnb ROI: 5.47% Traditional ROI: 4.27%
3513 Sunrise Drive Key West, FL A hidden gem nestled in our popular Sunrise Shores New Town district, this distinguished s...	3 beds \| 3 baths \| 2,569 sq.ft.	$2,265,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 2.12% Airbnb Rental Income: $11088 Traditional Rental Income: $7891 Airbnb ROI: 2.67% Traditional ROI: 2.12%
1209 Packer Street Key West, FL Discover a seamless blend of historic character and modern refinement at 1209 Packer Stree...	4 beds \| 4 baths \| 2,150 sq.ft.	$2,175,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 1.79% Airbnb Rental Income: $8036 Traditional Rental Income: $7021 Airbnb ROI: 1.53% Traditional ROI: 1.79%
1019 Eaton Street Key West, FL Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home i...	3 beds \| 2 baths \| 1,458 sq.ft.	$2,195,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 0.98% Airbnb Rental Income: $12364 Traditional Rental Income: $5409 Airbnb ROI: 3.29% Traditional ROI: 0.98%
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.	$2,449,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 1.73% Airbnb Rental Income: $1277 Traditional Rental Income: $7255 Airbnb ROI: -1.08% Traditional ROI: 1.73%
1320 South Street Key West, FL Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and o...	4 beds \| 5 baths \| 3,220 sq.ft.	$2,895,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 1.13% Airbnb Rental Income: $1277 Traditional Rental Income: $7469 Airbnb ROI: -1.33% Traditional ROI: 1.13%
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: 3.63% Airbnb Rental Income: $6590 Traditional Rental Income: $3403 Airbnb ROI: 6.87% Traditional ROI: 3.63%
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.	$1,680,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 2.42% Airbnb Rental Income: $11580 Traditional Rental Income: $6631 Airbnb ROI: 4.23% Traditional ROI: 2.42%
1911 Seidenberg Avenue Key West, FL With only two owners in its history, this well-maintained two-story property presents a ra...	2 beds \| 2 baths \| 1,119 sq.ft.	$1,250,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 1.33% Airbnb Rental Income: $2371 Traditional Rental Income: $3048 Airbnb ROI: 0.24% Traditional ROI: 1.33%
3405 16th Terrace Key West, FL Spacious, Turn-key Retreat on one of New Town's Largest Lots:Welcome to a rare opportunity...	4 beds \| 3 baths \| 2,050 sq.ft.	$1,575,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.04% Airbnb Rental Income: $9315 Traditional Rental Income: $6902 Airbnb ROI: 3.5% Traditional ROI: 3.04%
202 Admirals Lane Key West, FL Located in a gated community within the highly sought-after Truman Annex in Old Town Key W...	5 beds \| 4 baths \| 3,148 sq.ft.	$4,350,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 0.17% Airbnb Rental Income: $11896 Traditional Rental Income: $8025 Airbnb ROI: 0.6% Traditional ROI: 0.17%
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: 4.11% Airbnb Rental Income: $7456 Traditional Rental Income: $4675 Airbnb ROI: 5.79% Traditional ROI: 4.11%
1012 Packer Street #UNIT 7A Key West, FL PRICE REDUCTION!! This secluded condo is close to all the fun Key West has to offer, inclu...	2 beds \| 2 baths \| 768 sq.ft.	$779,000	Airbnb cash on cash: 7.38% Traditional cash on cash: 3.33% Airbnb Rental Income: $8333 Traditional Rental Income: $3815 Airbnb ROI: 7.38% Traditional ROI: 3.33%
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: 1.29% Airbnb Rental Income: $9315 Traditional Rental Income: $6602 Airbnb ROI: 1.69% Traditional ROI: 1.29%
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.	$660,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 3.54% Airbnb Rental Income: $7456 Traditional Rental Income: $3883 Airbnb ROI: 7.02% Traditional ROI: 3.54%
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%
314 Avenue D Key West, FL Elevated 3-Bedroom 2-Bath home with huge yard and low insurance rates! Upon entering you a...	3 beds \| 2 baths \| 1,431 sq.ft.	$875,000	Airbnb cash on cash: 9.5% Traditional cash on cash: 2.76% Airbnb Rental Income: $11088 Traditional Rental Income: $3559 Airbnb ROI: 9.5% Traditional ROI: 2.76%
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%
2924 Riviera Drive Key West, FL Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full b...	3 beds \| 4 baths \| 2,469 sq.ft.	$2,549,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.49% Airbnb Rental Income: $11088 Traditional Rental Income: $9019 Airbnb ROI: 2.5% Traditional ROI: 2.49%
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%
90 Golf Club Drive Key West, FL Seller Motivated. This charming Poolside Key West Golf Club home is ready for you to make ...	2 beds \| 3 baths \| 930 sq.ft.	$719,000	Airbnb cash on cash: 6.95% Traditional cash on cash: 4.29% Airbnb Rental Income: $7456 Traditional Rental Income: $4241 Airbnb ROI: 6.95% Traditional ROI: 4.29%
2330 Staples Avenue Key West, FL Discover a rare investment opportunity in the heart of Key West. This spacious corner dup...	1 beds \| 1 baths \| 693 sq.ft.	$1,100,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.86% Airbnb Rental Income: $2797 Traditional Rental Income: $3548 Airbnb ROI: 0.49% Traditional ROI: 1.86%
1230 5th Street Key West, FL Centrally located to everything Key West has to offer, and tucked behind a concrete privac...	3 beds \| 4 baths \| 2,236 sq.ft.	$1,475,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 2.01% Airbnb Rental Income: $2385 Traditional Rental Income: $5160 Airbnb ROI: -0.44% Traditional ROI: 2.01%
3700 Eagle Avenue Key West, FL Set on the highly desirable upper end of Eagle Avenue, this four bedroom, three bath home ...	4 beds \| 3 baths \| 2,733 sq.ft.	$1,689,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.76% Airbnb Rental Income: $9315 Traditional Rental Income: $6958 Airbnb ROI: 3.15% Traditional ROI: 2.76%
817 Terry Lane Key West, FL Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cott...	1 beds \| 1 baths \| 420 sq.ft.	$998,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 2% Airbnb Rental Income: $6911 Traditional Rental Income: $3425 Airbnb ROI: 4.31% Traditional ROI: 2%
27 Riviera Dr Key West, FL Welcome to your own slice of paradise in the Florida Keys! This wonderful opportunity offe...	2 beds \| 2 baths \| 1,200 sq.ft.	$699,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 6% Airbnb Rental Income: $7456 Traditional Rental Income: $5162 Airbnb ROI: 7.33% Traditional ROI: 6%
3741 Eagle Avenue Key West, FL Experience refined island living in this BRAND NEW residence perfectly situated on a gener...	3 beds \| 4 baths \| 2,744 sq.ft.	$3,900,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.77% Airbnb Rental Income: $11088 Traditional Rental Income: $7071 Airbnb ROI: 1.32% Traditional ROI: 0.77%
1022 Fleming Street Key West, FL Invest in Key West with this Duplex which can be also easily used as a single family home!...	4 beds \| 2 baths \| 2,016 sq.ft.	$1,650,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 1.84% Airbnb Rental Income: $10441 Traditional Rental Income: $5785 Airbnb ROI: 3.62% Traditional ROI: 1.84%
2805 Flagler Avenue Key West, FL This sophisticated residence features off-street parking for two vehicles or a boat and is...	3 beds \| 2 baths \| 1,227 sq.ft.	$874,999	Airbnb cash on cash: 9.3% Traditional cash on cash: 2.25% Airbnb Rental Income: $11088 Traditional Rental Income: $3309 Airbnb ROI: 9.3% Traditional ROI: 2.25%
1800 Atlantic Boulevard #UNIT 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%
1109 Stump Lane Key West, FL On a quiet lane in Old Town, this classic Conch home offers a setting where life feels jus...	3 beds \| 4 baths \| 1,724 sq.ft.	$2,299,500	Airbnb cash on cash: 2.59% Traditional cash on cash: 1.24% Airbnb Rental Income: $11712 Traditional Rental Income: $6695 Airbnb ROI: 2.59% Traditional ROI: 1.24%
2911 Seidenberg Avenue Key West, FL Welcome to your dream home in the heart of Key West's MidTown!This beautifully updated 3-...	3 beds \| 2 baths \| 1,052 sq.ft.	$1,195,000	Airbnb cash on cash: 6.42% Traditional cash on cash: 2.86% Airbnb Rental Income: $11088 Traditional Rental Income: $5095 Airbnb ROI: 6.42% Traditional ROI: 2.86%
411 Louisa Street Key West, FL Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located...	5 beds \| 5 baths \| 3,663 sq.ft.	$6,750,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.44% Airbnb Rental Income: $11896 Traditional Rental Income: $11082 Airbnb ROI: 0.22% Traditional ROI: 0.44%
1427 Washington Street Key West, FL Located in a charming midtown neighborhood sits this beautifully renovated 4BD/2.5BA Key W...	4 beds \| 3 baths \| 2,051 sq.ft.	$2,525,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 1.11% Airbnb Rental Income: $1277 Traditional Rental Income: $5909 Airbnb ROI: -1.03% Traditional ROI: 1.11%
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: -0.51% Traditional cash on cash: -0.8% Airbnb Rental Income: $12364 Traditional Rental Income: $8263 Airbnb ROI: -0.51% Traditional ROI: -0.8%
410 Louisa Street Key West, FL Experience the epitome of luxury in this exquisite 3BD/3BA residence nestled on a quiet La...	3 beds \| 3 baths \| 2,002 sq.ft.	$2,699,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 0.71% Airbnb Rental Income: $11712 Traditional Rental Income: $5719 Airbnb ROI: 2.25% Traditional ROI: 0.71%
3 Nassau Lane #UNIT A Key West, FL Charming Key West Cottage on Historic Nassau LaneNestled along the picturesque and histori...	1 beds \| 1 baths \| 468 sq.ft.	$825,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 2.68% Airbnb Rental Income: $6628 Traditional Rental Income: $3397 Airbnb ROI: 5.2% Traditional ROI: 2.68%
32 Golf Club Drive Key West, FL 3BR/2.5BA 2-story townhouse with its own private pool and professionally landscaped yard w...	3 beds \| 3 baths \| 1,060 sq.ft.	$999,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 2.83% Airbnb Rental Income: $11088 Traditional Rental Income: $4319 Airbnb ROI: 7.92% Traditional ROI: 2.83%
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: 6.82% Traditional cash on cash: 2.39% Airbnb Rental Income: $11712 Traditional Rental Income: $4639 Airbnb ROI: 6.82% Traditional ROI: 2.39%

Real Estate investment in Key-west, FL

There are 192 properties for sale in the city of Key West . The median list price in Key West is $1,350,000 and the average price per square foot is $827. In May 2026, the average monthly cash on cash return in Key West is 1.00%. The average monthly rental income in Key West is $3,313.

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

There are 192 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 $2,938.

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.

$2,250,000

Airbnb cash on cash: 2.97%

Traditional cash on cash: 1.03%

Airbnb Rental Income: $11712

Traditional Rental Income: $5529

Airbnb ROI: 2.97%

Traditional ROI: 1.03%

224 Golf Club Drive

Key West, FL

2 beds | 3 baths | 1,120 sq.ft.

$875,000

Airbnb cash on cash: 5.47%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $7456

Traditional Rental Income: $5046

Airbnb ROI: 5.47%

Traditional ROI: 4.27%

3513 Sunrise Drive

Key West, FL

3 beds | 3 baths | 2,569 sq.ft.

$2,265,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $11088

Traditional Rental Income: $7891

Airbnb ROI: 2.67%

Traditional ROI: 2.12%

1209 Packer Street

Key West, FL

4 beds | 4 baths | 2,150 sq.ft.

$2,175,000

Airbnb cash on cash: 1.53%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $8036

Traditional Rental Income: $7021

Airbnb ROI: 1.53%

Traditional ROI: 1.79%

1019 Eaton Street

Key West, FL

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

$2,195,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $12364

Traditional Rental Income: $5409

Airbnb ROI: 3.29%

Traditional ROI: 0.98%

1320 Eliza Street

Key West, FL

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

$2,449,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $1277

Traditional Rental Income: $7255

Airbnb ROI: -1.08%

Traditional ROI: 1.73%

1320 South Street

Key West, FL

4 beds | 5 baths | 3,220 sq.ft.

$2,895,000

Airbnb cash on cash: -1.33%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $1277

Traditional Rental Income: $7469

Airbnb ROI: -1.33%

Traditional ROI: 1.13%

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: 3.63%

Airbnb Rental Income: $6590

Traditional Rental Income: $3403

Airbnb ROI: 6.87%