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.

Investment Property for Sale in Islamorada, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
183 Azalea Street ISLAMORADA, FL Boater's Delight! Nestled in desirable Plantation Key Colony on a deep water canal, this c...	3 beds \| 3 baths \| 2,048 sq.ft.	$1,879,999	Airbnb cash on cash: 1.4% Traditional cash on cash: 0.86% Airbnb Rental Income: $6036 Traditional Rental Income: $3901 Airbnb ROI: 1.4% Traditional ROI: 0.86%
100 Iroquois Drive #8 ISLAMORADA, FL Welcome to your own paradise in Islamorada, Florida! This stunning retreat offers the perf...	3 beds \| 3 baths \| 1,764 sq.ft.	$799,999	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.39% Airbnb Rental Income: $6036 Traditional Rental Income: $3677 Airbnb ROI: 4.95% Traditional ROI: 3.39%
87200 Overseas Hwy #C3 ISLAMORADA, FL Beautiful move-in ready, meticulously just renovated 2bed/2bath townhome condo in the hear...	2 beds \| 2 baths \| 1,352 sq.ft.	$646,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 1.35% Airbnb Rental Income: $6227 Traditional Rental Income: $3282 Airbnb ROI: 4.2% Traditional ROI: 1.35%
87200 Overseas Hwy #A7 ISLAMORADA, FL Experience the ultimate Florida Keys lifestyle in this stunning 2-bedroom condo. Nestled i...	2 beds \| 2 baths \| 1,337 sq.ft.	$629,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 0.24% Airbnb Rental Income: $6227 Traditional Rental Income: $2699 Airbnb ROI: 4.16% Traditional ROI: 0.24%
87200 Overseas Hwy #P8 ISLAMORADA, FL Discover the ultimate in Florida Keys living with this fully renovated 2-bed, 2-bath villa...	2 beds \| 2 baths \| 1,359 sq.ft.	$649,900	Airbnb cash on cash: 3.91% Traditional cash on cash: 0.98% Airbnb Rental Income: $6227 Traditional Rental Income: $3221 Airbnb ROI: 3.91% Traditional ROI: 0.98%
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: 1.37% Traditional cash on cash: -0.05% Airbnb Rental Income: $6227 Traditional Rental Income: $3027 Airbnb ROI: 1.37% Traditional ROI: -0.05%
109 Columbus Drive ISLAMORADA, FL THE LAST RESORT offers breathtaking views of the Atlantic Ocean, complemented by expansive...	4 beds \| 5 baths \| 3,860 sq.ft.	$7,650,000	Airbnb cash on cash: 0.11% Traditional cash on cash: -0.58% Airbnb Rental Income: $13156 Traditional Rental Income: $5897 Airbnb ROI: 0.11% Traditional ROI: -0.58%
81216 Old Highway ISLAMORADA, FL Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an overs...	3 beds \| 3 baths \| 960 sq.ft.	$1,300,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.09% Airbnb Rental Income: $6036 Traditional Rental Income: $3214 Airbnb ROI: 2.44% Traditional ROI: 1.09%
80450 Overseas Highway #UNIT 107 ISLAMORADA, FL Significant price adjustment ... Owner looking for an offer on this on of a kind property ...	5 beds \| 3 baths \| 3,264 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.61% Airbnb Rental Income: $null Traditional Rental Income: $4296 Airbnb ROI: N/A Traditional ROI: 1.61%
81801 Overseas Highway #UNIT 416 ISLAMORADA, FL Exquisite Oceanfront at Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to you...	1 beds \| 1 baths \| 840 sq.ft.	$935,000	Airbnb cash on cash: 0.02% Traditional cash on cash: -1.07% Airbnb Rental Income: $4195 Traditional Rental Income: $2353 Airbnb ROI: 0.02% Traditional ROI: -1.07%
81801 Overseas Highway #UNIT 751 ISLAMORADA, FL Discover Your Island Retreat at Cheeca Lodge Resort and Spa Timeless Elegance Meets Contem...	1 beds \| 1 baths \| 358 sq.ft.	$649,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 1% Airbnb Rental Income: $4195 Traditional Rental Income: $1794 Airbnb ROI: 3.5% Traditional ROI: 1%
80459 Old Highway ISLAMORADA, FL 'Coconut Cottage' beckons you to the quintessence of tropical living in Islamorada. ...	5 beds \| 4 baths \| 2,358 sq.ft.	$4,495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.33% Airbnb Rental Income: $null Traditional Rental Income: $5453 Airbnb ROI: N/A Traditional ROI: -0.33%
81801 Overseas Highway #UNIT 612 ISLAMORADA, FL Cheeca Lodge Resort and Spa--the very name conjures up images of swaying palms, salt-kisse...	1 beds \| 1 baths \| 550 sq.ft.	$795,000	Airbnb cash on cash: -1.48% Traditional cash on cash: -3.79% Airbnb Rental Income: $4195 Traditional Rental Income: $1595 Airbnb ROI: -1.48% Traditional ROI: -3.79%
79901 Overseas Highway #UNIT 101 ISLAMORADA, FL Who says oceanfront living in the heart of the Florida Keys is not affordable? This cute ...	1 beds \| 1 baths \| 409 sq.ft.	$399,500	Airbnb cash on cash: 6.81% Traditional cash on cash: 2.49% Airbnb Rental Income: $4195 Traditional Rental Income: $1688 Airbnb ROI: 6.81% Traditional ROI: 2.49%
81801 Overseas Highway #UNIT 709 ISLAMORADA, FL Nightly Rental Condotel at Historic Cheeca Lodge Resort and Spa1. Condo Features: ...	1 beds \| 1 baths \| 550 sq.ft.	$720,000	Airbnb cash on cash: -1.56% Traditional cash on cash: -4.11% Airbnb Rental Income: $4195 Traditional Rental Income: $1595 Airbnb ROI: -1.56% Traditional ROI: -4.11%
81801 Overseas Highway #UNIT 712 ISLAMORADA, FL Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Spo...	1 beds \| 1 baths \| 550 sq.ft.	$725,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 1.08% Airbnb Rental Income: $4195 Traditional Rental Income: $1836 Airbnb ROI: 3.26% Traditional ROI: 1.08%
125 N Hammock Road ISLAMORADA, FL This beautiful 4-year-old ground-level home features 3 bedrooms and 2 bathrooms. The kitch...	3 beds \| 2 baths \| 1,518 sq.ft.	$1,100,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 1.25% Airbnb Rental Income: $6036 Traditional Rental Income: $2982 Airbnb ROI: 3.07% Traditional ROI: 1.25%
82779 Old Highway #UNIT 2 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$5,950,000	Airbnb cash on cash: -0.63% Traditional cash on cash: -1.43% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -0.63% Traditional ROI: -1.43%
82779 Old Highway #UNIT 4 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$5,500,000	Airbnb cash on cash: -2.88% Traditional cash on cash: -3.75% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -2.88% Traditional ROI: -3.75%
82779 Old Highway #UNIT 9 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$5,250,000	Airbnb cash on cash: -0.45% Traditional cash on cash: -1.36% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -0.45% Traditional ROI: -1.36%
82779 Old Highway #UNIT 13 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$5,500,000	Airbnb cash on cash: -0.52% Traditional cash on cash: -1.39% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -0.52% Traditional ROI: -1.39%
82779 Old Highway #UNIT 22 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$6,125,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -1.45% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -0.67% Traditional ROI: -1.45%
82779 Old Highway #UNIT 15 ISLAMORADA, FL The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offe...	4 beds \| 5 baths \| 2,574 sq.ft.	$4,950,000	Airbnb cash on cash: -0.36% Traditional cash on cash: -1.32% Airbnb Rental Income: $13156 Traditional Rental Income: $6345 Airbnb ROI: -0.36% Traditional ROI: -1.32%
83201 Old Highway #UNIT 405 ISLAMORADA, FL LOCATION, DOCKAGE. Dockage on the oceanside of Upper Matecumbe Key! ALSO Parking for car a...	2 beds \| 2 baths \| 1,275 sq.ft.	$1,275,000	Airbnb cash on cash: 1.67% Traditional cash on cash: -0.11% Airbnb Rental Income: $6227 Traditional Rental Income: $2890 Airbnb ROI: 1.67% Traditional ROI: -0.11%
191 Carroll Street ISLAMORADA, FL This newly remodeled 3 bedroom, 3 bathroom home is located on upper Matecumbe in the heart...	3 beds \| 3 baths \| 1,550 sq.ft.	$1,350,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 0.82% Airbnb Rental Income: $6036 Traditional Rental Income: $3110 Airbnb ROI: 2.2% Traditional ROI: 0.82%
81120 Old Highway ISLAMORADA, FL This stunning property offers a rare opportunity with two lots and over 24,000 square feet...	2 beds \| 1 baths \| 772 sq.ft.	$1,300,000	Airbnb cash on cash: 2.49% Traditional cash on cash: -0.05% Airbnb Rental Income: $6227 Traditional Rental Income: $1923 Airbnb ROI: 2.49% Traditional ROI: -0.05%
79901 Overseas Highway #UNIT 512 ISLAMORADA, FL Fabulous top floor location with spectacular ocean views! This spacious condo has tile fl...	2 beds \| 2 baths \| 981 sq.ft.	$775,000	Airbnb cash on cash: 3.69% Traditional cash on cash: -0.14% Airbnb Rental Income: $6227 Traditional Rental Income: $2234 Airbnb ROI: 3.69% Traditional ROI: -0.14%
81801 Overseas Highway #UNIT 208 ISLAMORADA, FL Exquisite Oceanfront at Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to you...	1 beds \| 1 baths \| 840 sq.ft.	$899,000	Airbnb cash on cash: 0.03% Traditional cash on cash: -1.11% Airbnb Rental Income: $4195 Traditional Rental Income: $2353 Airbnb ROI: 0.03% Traditional ROI: -1.11%
82260 Overseas Highway ISLAMORADA, FL Paradise Found: Renovated Jungle Treehouse!Welcome to your dream retreat in the heart of t...	3 beds \| 3 baths \| 2,808 sq.ft.	$1,350,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.87% Airbnb Rental Income: $6036 Traditional Rental Income: $5727 Airbnb ROI: 2.16% Traditional ROI: 2.87%
100 List Street ISLAMORADA, FL Welcome to Bahia Bonita! This ultra-private bayfront estate in the heart of downtown Islam...	3 beds \| 3 baths \| 3,019 sq.ft.	$7,495,000	Airbnb cash on cash: -0.48% Traditional cash on cash: -0.55% Airbnb Rental Income: $6036 Traditional Rental Income: $4372 Airbnb ROI: -0.48% Traditional ROI: -0.55%
80639 Old Highway #UNIT 201 ISLAMORADA, FL LAST New developer unit for sale in Maison Residences!Maison Residences #201, a 4 bedroom ...	4 beds \| 5 baths \| 2,539 sq.ft.	$3,495,000	Airbnb cash on cash: 0.77% Traditional cash on cash: -0.5% Airbnb Rental Income: $13156 Traditional Rental Income: $6666 Airbnb ROI: 0.77% Traditional ROI: -0.5%
84961 Old Highway #UNIT A1 ISLAMORADA, FL Rare Opportunity! A quaint concrete bunker in the heart of Islamorada, with ocean views, n...	1 beds \| 1 baths \| 406 sq.ft.	$325,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 3.31% Airbnb Rental Income: $4195 Traditional Rental Income: $1772 Airbnb ROI: 8.33% Traditional ROI: 3.31%
84961 Old Highway #UNIT 19 ISLAMORADA, FL Least expensive oceanfront lot with immediate building capability!! Owner wants offer! RAR...	2 beds \| 2 baths \| 693 sq.ft.	$545,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 3.3% Airbnb Rental Income: $6227 Traditional Rental Income: $2591 Airbnb ROI: 8.03% Traditional ROI: 3.3%
84745 Old Highway #UNIT 14 ISLAMORADA, FL Peaceful Palms - is a new construction luxury coastal property, in a gated community, loca...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,900,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.5% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 1.32% Traditional ROI: 0.5%
84745 Old Highway #UNIT 5 ISLAMORADA, FL Peaceful Palms - is a new construction luxury coastal property, in a gated community, loca...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,350,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 1.4% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 2.55% Traditional ROI: 1.4%
84745 Old Highway #UNIT 8 ISLAMORADA, FL Peaceful Palms - is a newly-built luxury coastal development situated in the gated communi...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,800,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 0.77% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 1.63% Traditional ROI: 0.77%
84745 Old Highway #UNIT 12 ISLAMORADA, FL Weekly Rentals available now. This upscale property features 15 high-end townhomes, all b...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,500,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.16% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 2.2% Traditional ROI: 1.16%
84745 Old Highway #UNIT 13 ISLAMORADA, FL Weekly rentals available starting in November. Peaceful Palms - is a newly-built luxury co...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,750,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 0.82% Airbnb Rental Income: $6036 Traditional Rental Income: $3393 Airbnb ROI: 1.71% Traditional ROI: 0.82%
84745 Old Highway #UNIT 4 ISLAMORADA, FL Seven day rentals allowed with a license. Peaceful Palms - is a new construction luxury co...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,200,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.11% Airbnb Rental Income: $6036 Traditional Rental Income: $3858 Airbnb ROI: 2.99% Traditional ROI: 2.11%
144 Anglers Way ISLAMORADA, FL RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in ...	2 beds \| 3 baths \| 1,674 sq.ft.	$2,150,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.3% Airbnb Rental Income: $6227 Traditional Rental Income: $3802 Airbnb ROI: 0.9% Traditional ROI: 0.3%

Real Estate investment in Islamorada, FL

There are 44 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,325,000 and the average price per square foot is $831. In December 2024, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $3,252.

Islamorada, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 44 investment properties available for sale in Islamorada.

In 2024, the best neighborhood to buy investment property is ISLAMORADA.

The ROI for Long-Term is higher than the Short-Term in Islamorada with average rental income of $3,252.

Your search for investment property begins and ends here

Investment Property for Sale in Islamorada, FL

183 Azalea Street

ISLAMORADA, FL

3 beds | 3 baths | 2,048 sq.ft.

$1,879,999

Airbnb cash on cash: 1.4%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $6036

Traditional Rental Income: $3901

Airbnb ROI: 1.4%

Traditional ROI: 0.86%

100 Iroquois Drive #8

ISLAMORADA, FL

3 beds | 3 baths | 1,764 sq.ft.

$799,999

Airbnb cash on cash: 4.95%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $6036

Traditional Rental Income: $3677

Airbnb ROI: 4.95%

Traditional ROI: 3.39%

87200 Overseas Hwy #C3

ISLAMORADA, FL

2 beds | 2 baths | 1,352 sq.ft.

$646,000

Airbnb cash on cash: 4.2%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $6227

Traditional Rental Income: $3282

Airbnb ROI: 4.2%

Traditional ROI: 1.35%

87200 Overseas Hwy #A7

ISLAMORADA, FL

2 beds | 2 baths | 1,337 sq.ft.

$629,000

Airbnb cash on cash: 4.16%

Traditional cash on cash: 0.24%

Airbnb Rental Income: $6227

Traditional Rental Income: $2699

Airbnb ROI: 4.16%

Traditional ROI: 0.24%

87200 Overseas Hwy #P8

ISLAMORADA, FL

2 beds | 2 baths | 1,359 sq.ft.

$649,900

Airbnb cash on cash: 3.91%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $6227

Traditional Rental Income: $3221

Airbnb ROI: 3.91%

Traditional ROI: 0.98%

120 Anglers Way

ISLAMORADA, FL

2 beds | 3 baths | 1,137 sq.ft.

$1,500,000

Airbnb cash on cash: 1.37%

Traditional cash on cash: -0.05%

Airbnb Rental Income: $6227

Traditional Rental Income: $3027

Airbnb ROI: 1.37%

Traditional ROI: -0.05%

109 Columbus Drive

ISLAMORADA, FL

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

$7,650,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: -0.58%

Airbnb Rental Income: $13156

Traditional Rental Income: $5897

Airbnb ROI: 0.11%

Traditional ROI: -0.58%

81216 Old Highway

ISLAMORADA, FL

3 beds | 3 baths | 960 sq.ft.

$1,300,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $6036

Traditional Rental Income: $3214

Airbnb ROI: 2.44%