Real Estate Investment Properties for Sale in Islamorada, FL

Looking for investment property in Islamorada, FL with high ROI ?

Explore a variety of short-term homes & houses in Islamorada, FL. Invest wisely with VRBO & Islamorada, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Islamorada, FL

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

Showing 34 Single Family Residential 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
109 Columbus Drive ISLAMORADA, FL Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfro...	4 beds \| 5 baths \| 3,860 sq.ft.	$6,700,000	Airbnb cash on cash: 0.24% Traditional cash on cash: -0.55% Airbnb Rental Income: $13156 Traditional Rental Income: $5897 Airbnb ROI: 0.24% Traditional ROI: -0.55%
82762 Overseas Highway #UNIT 3 ISLAMORADA, FL Open Bay Views, Boat Dockage, Pool and more... all in the Heart of Downtown Islamorada! Ha...	4 beds \| 4 baths \| 2,728 sq.ft.	$1,900,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 0.8% Airbnb Rental Income: $13156 Traditional Rental Income: $4986 Airbnb ROI: 4.08% Traditional ROI: 0.8%
81250 Overseas Highway #UNIT 2 ISLAMORADA, FL Experience refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront en...	3 beds \| 3 baths \| 2,072 sq.ft.	$2,850,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.03% Airbnb Rental Income: $6036 Traditional Rental Income: $6564 Airbnb ROI: -0.68% Traditional ROI: -0.03%
82260 Overseas Highway ISLAMORADA, FL This renovated treehouse retreat is your picture-perfect getaway or forever island home! D...	3 beds \| 3 baths \| 2,314 sq.ft.	$899,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 4.8% Airbnb Rental Income: $6036 Traditional Rental Income: $5727 Airbnb ROI: 3.74% Traditional ROI: 4.8%
81250 Overseas Highway #UNIT 5 ISLAMORADA, FL Only sophistication and class represented in Islamorada's most exclusive development, Tarp...	4 beds \| 3 baths \| 2,336 sq.ft.	$2,600,000	Airbnb cash on cash: 1.66% Traditional cash on cash: -1.03% Airbnb Rental Income: $13156 Traditional Rental Income: $4286 Airbnb ROI: 1.66% Traditional ROI: -1.03%
80201 Overseas Hwy ISLAMORADA, FL Experience Islamorada living at its absolute finest with this remodeled oceanfront estate....	5 beds \| 6 baths \| 4,764 sq.ft.	$7,800,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.47% Airbnb Rental Income: $null Traditional Rental Income: $5874 Airbnb ROI: N/A Traditional ROI: -0.47%
81906 Overseas Highway #UNIT 3 ISLAMORADA, FL Welcome to Coral Cove Residence 3, perfectly positioned in the heart of Islamorada. This t...	3 beds \| 4 baths \| 1,768 sq.ft.	$2,649,000	Airbnb cash on cash: -0.06% Traditional cash on cash: -0.24% Airbnb Rental Income: $6036 Traditional Rental Income: $4391 Airbnb ROI: -0.06% Traditional ROI: -0.24%
81906 Overseas Highway #UNIT 2 ISLAMORADA, FL Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places ...	3 beds \| 4 baths \| 1,829 sq.ft.	$2,495,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.27% Airbnb Rental Income: $6036 Traditional Rental Income: $4317 Airbnb ROI: -0.05% Traditional ROI: -0.27%
20 Park Rd ISLAMORADA, FL Downtown Islamorada gem located on a massive 11,000+ square-foot lot on a quiet street. Va...	2 beds \| 2 baths \| 1,120 sq.ft.	$875,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 1.05% Airbnb Rental Income: $6227 Traditional Rental Income: $2387 Airbnb ROI: 4.17% Traditional ROI: 1.05%
19 Avacado Street ISLAMORADA, FL Situated bayfront on an expansive 1.27-acre parcel, this striking contemporary residence c...	5 beds \| 7 baths \| 5,489 sq.ft.	$12,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.44% Airbnb Rental Income: $null Traditional Rental Income: $10001 Airbnb ROI: N/A Traditional ROI: -0.44%
33 Pen Key Drive ISLAMORADA, FL Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare...	3 beds \| 4 baths \| 4,537 sq.ft.	$2,495,000	Airbnb cash on cash: -23.63% Traditional cash on cash: -23.56% Airbnb Rental Income: $6036 Traditional Rental Income: $4999 Airbnb ROI: -23.63% Traditional ROI: -23.56%
104 Anglers Way ISLAMORADA, FL **This home is currently rented & no Available for showing until 04/02/2026**Exclusive...	2 beds \| 3 baths \| 1,376 sq.ft.	$1,299,999	Airbnb cash on cash: 2.34% Traditional cash on cash: 0.49% Airbnb Rental Income: $6227 Traditional Rental Income: $2764 Airbnb ROI: 2.34% Traditional ROI: 0.49%
84961 Old Highway #UNIT 21 ISLAMORADA, FL Stunning Ocean Views in Islamorada - the Fishing Capital of the World!Enjoy panoramic view...	2 beds \| 2 baths \| 946 sq.ft.	$1,295,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 1% Airbnb Rental Income: $6227 Traditional Rental Income: $2784 Airbnb ROI: 2.84% Traditional ROI: 1%
102 Anglers Way ISLAMORADA, FL ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community, T...	2 beds \| 3 baths \| 1,376 sq.ft.	$1,150,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.32% Airbnb Rental Income: $6227 Traditional Rental Income: $5183 Airbnb ROI: 2.15% Traditional ROI: 2.32%
316 N Dr ISLAMORADA, FL Simply the best location, exclusive & extremely private. It's tucked away in the prestigio...	3 beds \| 4 baths \| N/A	$2,750,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.51% Airbnb Rental Income: $6036 Traditional Rental Income: $5976 Airbnb ROI: 0.06% Traditional ROI: 0.51%
236 Costa Bravo Dr ISLAMORADA, FL A rare architectural masterpiece by renowned architect Max Strang, this modern coastal est...	5 beds \| 8 baths \| 6,367 sq.ft.	$14,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.6% Airbnb Rental Income: $null Traditional Rental Income: $9712 Airbnb ROI: N/A Traditional ROI: -0.6%
325 Calusa ISLAMORADA, FL This stunning three-story waterfront home offers panoramic ocean views from every level an...	3 beds \| 3 baths \| 1,619 sq.ft.	$2,300,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.07% Airbnb Rental Income: $6036 Traditional Rental Income: $3620 Airbnb ROI: 0.64% Traditional ROI: 0.07%
75433 Overseas Hwy Lower Matecumbe, FL Sandy Beach Cove â A Luxurious Island Retreat Nestled in the heart of Islamorada, Sandy ...	4 beds \| 4 baths \| 2,624 sq.ft.	$4,189,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 0.92% Airbnb Rental Income: $13156 Traditional Rental Income: $9641 Airbnb ROI: 1.21% Traditional ROI: 0.92%
82779 Old Highway #UNIT 17 ISLAMORADA, FL The Villas at the Islands of Islamorada is a meticulously designed, private gated communit...	4 beds \| 5 baths \| 2,574 sq.ft.	$3,800,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 0.65% Airbnb Rental Income: $13156 Traditional Rental Income: $6454 Airbnb ROI: 1.88% Traditional ROI: 0.65%
120 Anglers Way ISLAMORADA, FL Islamorada Exclusive Anglers Reef Resort! An oceanfront gated community with resort -style...	2 beds \| 3 baths \| 1,137 sq.ft.	$1,500,000	Airbnb cash on cash: 1.35% Traditional cash on cash: -0.06% Airbnb Rental Income: $6227 Traditional Rental Income: $3027 Airbnb ROI: 1.35% Traditional ROI: -0.06%
141 El Capitan Drive ISLAMORADA, FL Stunning Waterfront Oasis in Port Antigua Welcome to your dream home in the Florida Keys-a...	4 beds \| 3 baths \| 2,098 sq.ft.	$2,650,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 0.55% Airbnb Rental Income: $13156 Traditional Rental Income: $4487 Airbnb ROI: 3.11% Traditional ROI: 0.55%

Your search for investment property begins and ends here

Single Family Homes for Sale in Islamorada, FL

109 Columbus Drive

ISLAMORADA, FL

4 beds | 5 baths | 3,860 sq.ft.

$6,700,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: -0.55%

Airbnb Rental Income: $13156

Traditional Rental Income: $5897

Airbnb ROI: 0.24%

Traditional ROI: -0.55%

82762 Overseas Highway #UNIT 3

ISLAMORADA, FL

4 beds | 4 baths | 2,728 sq.ft.

$1,900,000

Airbnb cash on cash: 4.08%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $13156

Traditional Rental Income: $4986

Airbnb ROI: 4.08%

Traditional ROI: 0.8%

81250 Overseas Highway #UNIT 2

ISLAMORADA, FL

3 beds | 3 baths | 2,072 sq.ft.

$2,850,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $6036

Traditional Rental Income: $6564

Airbnb ROI: -0.68%

Traditional ROI: -0.03%

82260 Overseas Highway

ISLAMORADA, FL

3 beds | 3 baths | 2,314 sq.ft.

$899,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $6036

Traditional Rental Income: $5727

Airbnb ROI: 3.74%

Traditional ROI: 4.8%

81250 Overseas Highway #UNIT 5

ISLAMORADA, FL

4 beds | 3 baths | 2,336 sq.ft.

$2,600,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: -1.03%

Airbnb Rental Income: $13156

Traditional Rental Income: $4286

Airbnb ROI: 1.66%

Traditional ROI: -1.03%

80201 Overseas Hwy

ISLAMORADA, FL

5 beds | 6 baths | 4,764 sq.ft.

$7,800,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.47%

Airbnb Rental Income: $null

Traditional Rental Income: $5874

Airbnb ROI: N/A

Traditional ROI: -0.47%

81906 Overseas Highway #UNIT 3

ISLAMORADA, FL

3 beds | 4 baths | 1,768 sq.ft.

$2,649,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $6036

Traditional Rental Income: $4391

Airbnb ROI: -0.06%

Traditional ROI: -0.24%

81906 Overseas Highway #UNIT 2

ISLAMORADA, FL

3 beds | 4 baths | 1,829 sq.ft.

$2,495,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $6036

Traditional Rental Income: $4317

Airbnb ROI: -0.05%