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 28 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: -1% Traditional cash on cash: 0.07% Airbnb Rental Income: $3974 Traditional Rental Income: $9745 Airbnb ROI: -1% Traditional ROI: 0.07%
81250 Overseas Highway #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: 0.87% Traditional cash on cash: -0.34% Airbnb Rental Income: $7372 Traditional Rental Income: $2768 Airbnb ROI: 0.87% Traditional ROI: -0.34%
36 Park Road ISLAMORADA, FL Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new grou...	4 beds \| 3 baths \| 2,277 sq.ft.	$1,600,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 1.9% Airbnb Rental Income: $3974 Traditional Rental Income: $4724 Airbnb ROI: 0.82% Traditional ROI: 1.9%
81250 Overseas Highway #5 ISLAMORADA, FL Only sophistication and class represented in Islamorada's most exclusive development, Tarp...	4 beds \| 3 baths \| 2,336 sq.ft.	$2,290,000	Airbnb cash on cash: -0.18% Traditional cash on cash: -0.26% Airbnb Rental Income: $3974 Traditional Rental Income: $2954 Airbnb ROI: -0.18% Traditional ROI: -0.26%
80201 Overseas Highway ISLAMORADA, FL Experience Islamorada living at its absolute finest with this remodeled oceanfront estate....	5 beds \| 6 baths \| 4,764 sq.ft.	$7,400,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.79% Airbnb Rental Income: $885 Traditional Rental Income: $14239 Airbnb ROI: -1.2% Traditional ROI: 0.79%
82749 Old Highway ISLAMORADA, FL Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old H...	3 beds \| 3 baths \| 1,485 sq.ft.	$6,900,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.39% Airbnb Rental Income: $7372 Traditional Rental Income: $4566 Airbnb ROI: -0.17% Traditional ROI: -0.39%
189 Carroll Street ISLAMORADA, FL Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This beautifully remodeled 3...	3 beds \| 3 baths \| 1,525 sq.ft.	$1,250,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 1.53% Airbnb Rental Income: $7372 Traditional Rental Income: $3653 Airbnb ROI: 3.51% Traditional ROI: 1.53%
191 Carroll Street ISLAMORADA, FL Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This newly remodeled 3-bedro...	3 beds \| 3 baths \| 1,550 sq.ft.	$1,250,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.47% Airbnb Rental Income: $7372 Traditional Rental Income: $3683 Airbnb ROI: 3.43% Traditional ROI: 1.47%
32 Park Road ISLAMORADA, FL Ideally located in the heart of Islamorada, this charming home is perfectly updated with a...	3 beds \| 2 baths \| 1,224 sq.ft.	$1,300,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 1.16% Airbnb Rental Income: $7372 Traditional Rental Income: $3436 Airbnb ROI: 3.24% Traditional ROI: 1.16%
81906 Overseas Highway #2 ISLAMORADA, FL Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places y...	3 beds \| 4 baths \| 1,829 sq.ft.	$2,495,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 0.1% Airbnb Rental Income: $7372 Traditional Rental Income: $4079 Airbnb ROI: 0.91% Traditional ROI: 0.1%
82779 Old Highway #14 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% Traditional cash on cash: -0.05% Airbnb Rental Income: $3974 Traditional Rental Income: $6459 Airbnb ROI: -1% Traditional ROI: -0.05%
150 List Street ISLAMORADA, FL Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real est...	1 beds \| 1 baths \| 946 sq.ft.	$4,900,000	Airbnb cash on cash: -0.32% Traditional cash on cash: -0.49% Airbnb Rental Income: $4680 Traditional Rental Income: $2965 Airbnb ROI: -0.32% Traditional ROI: -0.49%
82779 Old Highway #7 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: -1.63% Traditional cash on cash: -0.56% Airbnb Rental Income: $3974 Traditional Rental Income: $6888 Airbnb ROI: -1.63% Traditional ROI: -0.56%
82779 Old Highway #8 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: -1.63% Traditional cash on cash: -0.56% Airbnb Rental Income: $3974 Traditional Rental Income: $6888 Airbnb ROI: -1.63% Traditional ROI: -0.56%
82779 Old Highway #15 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: -1.63% Traditional cash on cash: -0.56% Airbnb Rental Income: $3974 Traditional Rental Income: $6888 Airbnb ROI: -1.63% Traditional ROI: -0.56%
124 S Hammock Road ISLAMORADA, FL Nestled in the heart of Islamorada, this ground-level residence captures the essence of ti...	3 beds \| 2 baths \| 1,305 sq.ft.	$789,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 2.92% Airbnb Rental Income: $7372 Traditional Rental Income: $3497 Airbnb ROI: 6.27% Traditional ROI: 2.92%
33 Pen Key ISLAMORADA, FL Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare ...	3 beds \| 4 baths \| 4,537 sq.ft.	$2,195,000	Airbnb cash on cash: -26.17% Traditional cash on cash: -26.18% Airbnb Rental Income: $7372 Traditional Rental Income: $5923 Airbnb ROI: -26.17% Traditional ROI: -26.18%
143 N Hammock Road ISLAMORADA, FL Experience all that Islamorada has to offer from this stunning home that was constructed i...	3 beds \| 3 baths \| 2,022 sq.ft.	$1,199,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 1.07% Airbnb Rental Income: $7372 Traditional Rental Income: $3223 Airbnb ROI: 3.52% Traditional ROI: 1.07%
104 Anglers Way ISLAMORADA, FL Exclusive Anglers Reef Resort-style oceanfront home in Islamorada -- a rare coastal gem. N...	2 beds \| 3 baths \| 1,376 sq.ft.	$1,300,000	Airbnb cash on cash: 1% Traditional cash on cash: 0.89% Airbnb Rental Income: $4286 Traditional Rental Income: $3246 Airbnb ROI: 1% Traditional ROI: 0.89%
102 Anglers Way ISLAMORADA, FL ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community th...	2 beds \| 3 baths \| 1,376 sq.ft.	$1,150,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.63% Airbnb Rental Income: $4286 Traditional Rental Income: $3378 Airbnb ROI: 0.64% Traditional ROI: 0.63%
84961 Old Highway #18 ISLAMORADA, FL Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept...	2 beds \| 2 baths \| 793 sq.ft.	$999,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 1.47% Airbnb Rental Income: $4286 Traditional Rental Income: $3171 Airbnb ROI: 1.7% Traditional ROI: 1.47%
84961 Old Highway lot: 27 ISLAMORADA, FL Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buye...	1 beds \| 1 baths \| 468 sq.ft.	$899,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 0.87% Airbnb Rental Income: $4680 Traditional Rental Income: $2016 Airbnb ROI: 2.9% Traditional ROI: 0.87%
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	$2,500,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.44% Airbnb Rental Income: $7372 Traditional Rental Income: $7787 Airbnb ROI: 0.65% Traditional ROI: 1.44%
164 Venetian Dr ISLAMORADA, FL Boaterâs dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home...	4 beds \| 2 baths \| 1,680 sq.ft.	$1,549,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 1.25% Airbnb Rental Income: $3974 Traditional Rental Income: $4362 Airbnb ROI: 0.38% Traditional ROI: 1.25%
130 N Hammock Road ISLAMORADA, FL Island Life in the Heart of Islamorada, a ground-level, 3 bed, 2 bath home with all the ch...	3 beds \| 2 baths \| 1,376 sq.ft.	$645,000	Airbnb cash on cash: 7.79% Traditional cash on cash: 3.98% Airbnb Rental Income: $7372 Traditional Rental Income: $3661 Airbnb ROI: 7.79% Traditional ROI: 3.98%
126 Columbus Dr ISLAMORADA, FL Seller will consider seller financing. Florida Keys waterfront home, offered fully furnish...	3 beds \| 3 baths \| 1,786 sq.ft.	$1,499,999	Airbnb cash on cash: 2.47% Traditional cash on cash: 1.85% Airbnb Rental Income: $7372 Traditional Rental Income: $5089 Airbnb ROI: 2.47% Traditional ROI: 1.85%

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: -1%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $3974

Traditional Rental Income: $9745

Airbnb ROI: -1%

Traditional ROI: 0.07%

81250 Overseas Highway #2

ISLAMORADA, FL

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

$2,850,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: -0.34%

Airbnb Rental Income: $7372

Traditional Rental Income: $2768

Airbnb ROI: 0.87%

Traditional ROI: -0.34%

36 Park Road

ISLAMORADA, FL

4 beds | 3 baths | 2,277 sq.ft.

$1,600,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 1.9%

Airbnb Rental Income: $3974

Traditional Rental Income: $4724

Airbnb ROI: 0.82%

Traditional ROI: 1.9%

81250 Overseas Highway #5

ISLAMORADA, FL

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

$2,290,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: -0.26%

Airbnb Rental Income: $3974

Traditional Rental Income: $2954

Airbnb ROI: -0.18%

Traditional ROI: -0.26%

80201 Overseas Highway

ISLAMORADA, FL

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

$7,400,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.79%

Airbnb Rental Income: $885

Traditional Rental Income: $14239

Airbnb ROI: -1.2%

Traditional ROI: 0.79%

82749 Old Highway

ISLAMORADA, FL

3 beds | 3 baths | 1,485 sq.ft.

$6,900,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: -0.39%

Airbnb Rental Income: $7372

Traditional Rental Income: $4566

Airbnb ROI: -0.17%

Traditional ROI: -0.39%

189 Carroll Street

ISLAMORADA, FL

3 beds | 3 baths | 1,525 sq.ft.

$1,250,000

Airbnb cash on cash: 3.51%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $7372

Traditional Rental Income: $3653

Airbnb ROI: 3.51%

Traditional ROI: 1.53%

191 Carroll Street

ISLAMORADA, FL

3 beds | 3 baths | 1,550 sq.ft.

$1,250,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $7372

Traditional Rental Income: $3683

Airbnb ROI: 3.43%