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
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%
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%
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%
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 #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: 0.82% Traditional cash on cash: 0.03% Airbnb Rental Income: $7372 Traditional Rental Income: $4024 Airbnb ROI: 0.82% Traditional ROI: 0.03%
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%
79901 Overseas Highway #204 ISLAMORADA, FL Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed ...	2 beds \| 2 baths \| 981 sq.ft.	$499,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 1.73% Airbnb Rental Income: $4286 Traditional Rental Income: $3108 Airbnb ROI: 2.32% Traditional ROI: 1.73%
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 #7 ISLAMORADA, FL Bring your toothbrush, everything else you need is included in this move-in ready property...	1 beds \| 1 baths \| 400 sq.ft.	$365,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 4.01% Airbnb Rental Income: $4680 Traditional Rental Income: $2176 Airbnb ROI: 8.5% Traditional ROI: 4.01%
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%
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%
84961 Old Highway #41 ISLAMORADA, FL ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or...	1 beds \| 1 baths \| N/A	$450,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 2.82% Airbnb Rental Income: $4680 Traditional Rental Income: $1913 Airbnb ROI: 7.08% Traditional ROI: 2.82%
81801 Overseas Highway #727 ISLAMORADA, FL Attention Investors! Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in ...	1 beds \| 1 baths \| 358 sq.ft.	$585,000	Airbnb cash on cash: 1.37% Traditional cash on cash: -1.08% Airbnb Rental Income: $4680 Traditional Rental Income: $2373 Airbnb ROI: 1.37% Traditional ROI: -1.08%
81801 Overseas Highway #729 ISLAMORADA, FL Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, inco...	1 beds \| 1 baths \| 550 sq.ft.	$699,000	Airbnb cash on cash: 1.2% Traditional cash on cash: -1.78% Airbnb Rental Income: $4680 Traditional Rental Income: $1767 Airbnb ROI: 1.2% Traditional ROI: -1.78%
80450 Overseas Highway #204 ISLAMORADA, FL Welcome to Sand Pebbles -- Islamorada's Hidden Gem. Located in the heart of the Village of...	2 beds \| 2 baths \| 1,261 sq.ft.	$629,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 0.42% Airbnb Rental Income: $4286 Traditional Rental Income: $2880 Airbnb ROI: 1.28% Traditional ROI: 0.42%
81801 Overseas Highway #637 ISLAMORADA, FL Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca ...	1 beds \| 1 baths \| 550 sq.ft.	$735,000	Airbnb cash on cash: 1.07% Traditional cash on cash: -1.72% Airbnb Rental Income: $4680 Traditional Rental Income: $1797 Airbnb ROI: 1.07% Traditional ROI: -1.72%
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%

Vacation Rentals in Islamorada

There are 23 vacation rental properties available for sale in the city of Islamorada . The median list price of Airbnb properties available for sale in Islamorada is $1,400,000 and the average price per square foot is $730. The cash on cash return on vacation rentals in Islamorada is N/A%. The average monthly short term rental income in Islamorada is $4,286.

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

There are 23 Airbnb properties available for sale in Islamorada.

In 2026, the best neighborhood to buy short term rental property is ISLAMORADA.

In June 2026, the average Airbnb occupancy rate in Islamorada is 29%.

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

126 Columbus Dr

ISLAMORADA, FL

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%

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%

130 N Hammock Road

ISLAMORADA, FL

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%

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%

Traditional ROI: 1.47%

32 Park Road

ISLAMORADA, FL

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 #3

ISLAMORADA, FL

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

$2,649,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $7372

Traditional Rental Income: $4024

Airbnb ROI: 0.82%

Traditional ROI: 0.03%

81906 Overseas Highway #2

ISLAMORADA, FL

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%