Airbnb Properties for Sale in Islamorada, FL

Looking for a vacation rental investment in Islamorada, FL with high ROI ?

Explore a range of newly added short-term rental homes in Islamorada, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Islamorada, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
130 Anglers Way ISLAMORADA, FL ANGLERS REEF HOME in Islamorada. This home features 2 bedrooms, 2.5 bathrooms with carport...	2 beds \| 3 baths \| 1,170 sq.ft.	$1,299,999	Airbnb cash on cash: 2.43% Traditional cash on cash: 0.35% Airbnb Rental Income: $6227 Traditional Rental Income: $2481 Airbnb ROI: 2.43% Traditional ROI: 0.35%
75761 Overseas Highway ISLAMORADA, FL Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from ...	4 beds \| 4 baths \| 3,001 sq.ft.	$4,999,900	Airbnb cash on cash: 0.86% Traditional cash on cash: -0.28% Airbnb Rental Income: $13156 Traditional Rental Income: $5464 Airbnb ROI: 0.86% Traditional ROI: -0.28%
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%
87465 Old Hwy #102 ISLAMORADA, FL LIVE THE DREAM IN THIS OCEANFRONT BUILDING IN THE BEAUTIFUL FLORIDA KEYS! LARGER THAN OTHE...	2 beds \| 2 baths \| 1,100 sq.ft.	$428,000	Airbnb cash on cash: 8.63% Traditional cash on cash: 2.77% Airbnb Rental Income: $6227 Traditional Rental Income: $2648 Airbnb ROI: 8.63% Traditional ROI: 2.77%
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: 0.27% Traditional cash on cash: -0.52% Airbnb Rental Income: $13156 Traditional Rental Income: $5897 Airbnb ROI: 0.27% Traditional ROI: -0.52%
84745 Old Highway #UNIT 8 ISLAMORADA, FL Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a ...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,699,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.33% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 1.24% Traditional ROI: 0.33%
104 Anglers Way ISLAMORADA, FL Exclusive Anglers Reef Resort style Home in Islamorada. Experience the best of oceanfront ...	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%
84745 Old Highway #UNIT 7 ISLAMORADA, FL Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a ...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,499,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.5% Airbnb Rental Income: $6036 Traditional Rental Income: $3396 Airbnb ROI: 1.54% Traditional ROI: 0.5%
84745 Old Highway #UNIT 13 ISLAMORADA, FL Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a ...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,599,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.4% Airbnb Rental Income: $6036 Traditional Rental Income: $3393 Airbnb ROI: 1.38% Traditional ROI: 0.4%
84745 Old Highway #UNIT 4 ISLAMORADA, FL Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a ...	3 beds \| 3 baths \| 1,680 sq.ft.	$1,375,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.07% Airbnb Rental Income: $6036 Traditional Rental Income: $3858 Airbnb ROI: 1.84% Traditional ROI: 1.07%
79901 Overseas Highway #UNIT 403 ISLAMORADA, FL *UPDATED PRICING - $30,000 REDUCTION*RARE KEYS LIFESTYLE OPPORTUNITYThis isn't just a ...	2 beds \| 2 baths \| 981 sq.ft.	$679,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 0.04% Airbnb Rental Income: $6227 Traditional Rental Income: $2430 Airbnb ROI: 4.1% Traditional ROI: 0.04%
100 Seashore Drive ISLAMORADA, FL Welcome to Turtle's Nest, a charming home offering the perfect blend of comfort, flexibili...	3 beds \| 2 baths \| 2,128 sq.ft.	$1,600,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.72% Airbnb Rental Income: $6036 Traditional Rental Income: $3623 Airbnb ROI: 1.54% Traditional ROI: 0.72%
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.	$2,395,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 0.43% Airbnb Rental Income: $13156 Traditional Rental Income: $4986 Airbnb ROI: 3.03% Traditional ROI: 0.43%
83201 Old Highway #UNIT 409 ISLAMORADA, FL Welcome to Unit #409 at Beacon Reef, an oceanfront gem located in the heart of Islamorada....	2 beds \| 2 baths \| 1,275 sq.ft.	$1,099,000	Airbnb cash on cash: 1.64% Traditional cash on cash: -0.43% Airbnb Rental Income: $6227 Traditional Rental Income: $2889 Airbnb ROI: 1.64% Traditional ROI: -0.43%
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.	$1,650,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 1.16% Airbnb Rental Income: $13156 Traditional Rental Income: $3726 Airbnb ROI: 5.76% Traditional ROI: 1.16%
81801 Overseas Highway #UNIT 754 ISLAMORADA, FL Escape to island elegance in your own spacious King Suite at Cheeca Lodge and Spa. The Ico...	1 beds \| 1 baths \| 550 sq.ft.	$639,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 0.99% Airbnb Rental Income: $4195 Traditional Rental Income: $1685 Airbnb ROI: 3.71% Traditional ROI: 0.99%
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.	$795,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 2.34% Airbnb Rental Income: $6036 Traditional Rental Income: $3139 Airbnb ROI: 4.64% Traditional ROI: 2.34%
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.	$2,850,000	Airbnb cash on cash: 1.43% Traditional cash on cash: -1.03% Airbnb Rental Income: $13156 Traditional Rental Income: $4286 Airbnb ROI: 1.43% Traditional ROI: -1.03%
79901 Overseas Highway #UNIT 516 ISLAMORADA, FL Stunning and Expansive Open Ocean Views and views of Alligator Lighthouse from almost ever...	3 beds \| 2 baths \| 1,484 sq.ft.	$1,500,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 0.06% Airbnb Rental Income: $6036 Traditional Rental Income: $3632 Airbnb ROI: 0.93% Traditional ROI: 0.06%
79901 Overseas Highway #UNIT 218 ISLAMORADA, FL Lowest priced unit at The Palms of Islamorada, one of the area's premier condo complexes! ...	1 beds \| 2 baths \| 827 sq.ft.	$449,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 1.47% Airbnb Rental Income: $4195 Traditional Rental Income: $2214 Airbnb ROI: 4.06% Traditional ROI: 1.47%
219 Preston Street ISLAMORADA, FL Rare Downtown Islamorada Opportunity! Located just off the Old Hwy, oceanside, in the soug...	4 beds \| 3 baths \| 1,766 sq.ft.	$1,250,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 1.77% Airbnb Rental Income: $6036 Traditional Rental Income: $4032 Airbnb ROI: 2.46% Traditional ROI: 1.77%
218 Matecumbe Avenue ISLAMORADA, FL Build Your Dream -- Without the Wait! This rare Islamorada property is a true gem, offerin...	3 beds \| 3 baths \| 1,071 sq.ft.	$1,199,999	Airbnb cash on cash: 2.62% Traditional cash on cash: 0.64% Airbnb Rental Income: $6036 Traditional Rental Income: $2623 Airbnb ROI: 2.62% Traditional ROI: 0.64%

Vacation Rentals in Islamorada

There are 22 vacation rental properties available for sale in the city of Islamorada . The median list price of Airbnb properties available for sale in Islamorada is $1,549,500 and the average price per square foot is $810. The cash on cash return on vacation rentals in Islamorada is 1.00%. The average monthly short term rental income in Islamorada is $6,036.

Islamorada, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 22 Airbnb properties available for sale in Islamorada.

In 2025, the best neighborhood to buy short term rental property is ISLAMORADA.

In October 2025, the average Airbnb occupancy rate in Islamorada is 57%.

Airbnb data on vacation rentals in Islamorada, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Islamorada, FL market insights, guest information and booking details, seasonality trends and historical Islamorada, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Islamorada, FL

130 Anglers Way

ISLAMORADA, FL

2 beds | 3 baths | 1,170 sq.ft.

$1,299,999

Airbnb cash on cash: 2.43%

Traditional cash on cash: 0.35%

Airbnb Rental Income: $6227

Traditional Rental Income: $2481

Airbnb ROI: 2.43%

Traditional ROI: 0.35%

75761 Overseas Highway

ISLAMORADA, FL

4 beds | 4 baths | 3,001 sq.ft.

$4,999,900

Airbnb cash on cash: 0.86%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $13156

Traditional Rental Income: $5464

Airbnb ROI: 0.86%

Traditional ROI: -0.28%

120 Anglers Way

ISLAMORADA, FL

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%

87465 Old Hwy #102

ISLAMORADA, FL

2 beds | 2 baths | 1,100 sq.ft.

$428,000

Airbnb cash on cash: 8.63%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $6227

Traditional Rental Income: $2648

Airbnb ROI: 8.63%

Traditional ROI: 2.77%

109 Columbus Drive

ISLAMORADA, FL

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

$6,700,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: -0.52%

Airbnb Rental Income: $13156

Traditional Rental Income: $5897

Airbnb ROI: 0.27%

Traditional ROI: -0.52%

84745 Old Highway #UNIT 8

ISLAMORADA, FL

3 beds | 3 baths | 1,680 sq.ft.

$1,699,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $6036

Traditional Rental Income: $3396

Airbnb ROI: 1.24%

Traditional ROI: 0.33%

104 Anglers Way

ISLAMORADA, FL

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%

84745 Old Highway #UNIT 7

ISLAMORADA, FL

3 beds | 3 baths | 1,680 sq.ft.

$1,499,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $6036

Traditional Rental Income: $3396

Airbnb ROI: 1.54%