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
80450 Overseas Highway #UNIT 302 ISLAMORADA, FL Welcome to Sand Pebbles Condominium in the heart of Islamorada--an exclusive bayfront comm...	2 beds \| 2 baths \| 1,300 sq.ft.	$629,999	Airbnb cash on cash: 3.16% Traditional cash on cash: -0.51% Airbnb Rental Income: $5754 Traditional Rental Income: $2448 Airbnb ROI: 3.16% Traditional ROI: -0.51%
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: 0.05% Traditional cash on cash: -0.35% Airbnb Rental Income: $8621 Traditional Rental Income: $5157 Airbnb ROI: 0.05% Traditional ROI: -0.35%
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.	$1,699,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.08% Airbnb Rental Income: $8621 Traditional Rental Income: $4408 Airbnb ROI: 2.72% Traditional ROI: 1.08%
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: 0.91% Traditional cash on cash: 0.17% Airbnb Rental Income: $6746 Traditional Rental Income: $3850 Airbnb ROI: 0.91% Traditional ROI: 0.17%
75433 Overseas Hwy ISLAMORADA, FL Sandy Beach Cove - A Luxurious Island Retreat Nestled in the heart of Islamorada, Sandy Be...	4 beds \| 4 baths \| 2,624 sq.ft.	$3,999,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 0.29% Airbnb Rental Income: $8621 Traditional Rental Income: $6956 Airbnb ROI: 0.3% Traditional ROI: 0.29%
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 \| 1,032 sq.ft.	$428,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 2.57% Airbnb Rental Income: $5754 Traditional Rental Income: $3149 Airbnb ROI: 6.2% Traditional ROI: 2.57%
79901 Overseas Higway #204 ISLAMORADA, FL Spectacular Direct Ocean Views! ? Islamorada's Best-Kept Secret! This beautifully appointe...	2 beds \| 2 baths \| N/A	$569,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.04% Airbnb Rental Income: $5754 Traditional Rental Income: $3448 Airbnb ROI: 4.22% Traditional ROI: 2.04%
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: 3.05% Traditional cash on cash: 1.69% Airbnb Rental Income: $8344 Traditional Rental Income: $4868 Airbnb ROI: 3.05% Traditional ROI: 1.69%
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: 0.04% Traditional cash on cash: -0.64% Airbnb Rental Income: $8344 Traditional Rental Income: $4944 Airbnb ROI: 0.04% Traditional ROI: -0.64%
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: 3.43% Traditional cash on cash: 1.8% Airbnb Rental Income: $8621 Traditional Rental Income: $4573 Airbnb ROI: 3.43% Traditional ROI: 1.8%
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.	$680,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 3.62% Airbnb Rental Income: $8344 Traditional Rental Income: $3599 Airbnb ROI: 8.62% Traditional ROI: 3.62%
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: 0.09% Traditional cash on cash: -0.54% Airbnb Rental Income: $8621 Traditional Rental Income: $5466 Airbnb ROI: 0.09% Traditional ROI: -0.54%
83201 Old Highway #UNIT 405 ISLAMORADA, FL THIS UNIT COMES WITH COVERED PARKING. Not all units have covered parking. Covered parking ...	2 beds \| 2 baths \| 1,275 sq.ft.	$1,099,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 0.44% Airbnb Rental Income: $5754 Traditional Rental Income: $3445 Airbnb ROI: 1.49% Traditional ROI: 0.44%
189 Carroll Street ISLAMORADA, FL Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis beautifully remodeled 3-...	3 beds \| 3 baths \| 1,525 sq.ft.	$1,250,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 1.47% Airbnb Rental Income: $8344 Traditional Rental Income: $3587 Airbnb ROI: 4.2% Traditional ROI: 1.47%
191 Carroll Street ISLAMORADA, FL Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis newly remodeled 3-bedroo...	3 beds \| 3 baths \| 1,550 sq.ft.	$1,250,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 1.47% Airbnb Rental Income: $8344 Traditional Rental Income: $3674 Airbnb ROI: 4.13% 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: 3.91% Traditional cash on cash: 1.17% Airbnb Rental Income: $8344 Traditional Rental Income: $3452 Airbnb ROI: 3.91% Traditional ROI: 1.17%
100 List Street ISLAMORADA, FL Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada wit...	3 beds \| 3 baths \| 3,019 sq.ft.	$5,400,000	Airbnb cash on cash: 0.1% Traditional cash on cash: -0.13% Airbnb Rental Income: $8344 Traditional Rental Income: $5597 Airbnb ROI: 0.1% Traditional ROI: -0.13%
83201 Old Highway #UNIT 301 ISLAMORADA, FL Beacon Reef is calling your name! This beautifully designed 2-bedroom, 2-bath residence s...	2 beds \| 2 baths \| 1,275 sq.ft.	$850,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 0.55% Airbnb Rental Income: $5754 Traditional Rental Income: $3501 Airbnb ROI: 1.95% Traditional ROI: 0.55%
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: 0.72% Traditional cash on cash: -0.15% Airbnb Rental Income: $8344 Traditional Rental Income: $4607 Airbnb ROI: 0.72% Traditional ROI: -0.15%
83201 Old Highway #UNIT 504 ISLAMORADA, FL Exclusive Beacon Reef Unit 504 presents a rare opportunity in the heart of downtown Islamo...	2 beds \| 2 baths \| 1,275 sq.ft.	$950,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 0.02% Airbnb Rental Income: $5754 Traditional Rental Income: $3512 Airbnb ROI: 1.26% Traditional ROI: 0.02%
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: 0.78% Traditional cash on cash: -0.22% Airbnb Rental Income: $8344 Traditional Rental Income: $4436 Airbnb ROI: 0.78% Traditional ROI: -0.22%
20 Park Road 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: 3.83% Traditional cash on cash: 2.09% Airbnb Rental Income: $5754 Traditional Rental Income: $3184 Airbnb ROI: 3.83% Traditional ROI: 2.09%
82207 Old Highway ISLAMORADA, FL Ground-level living in the heart of Islamorada! Situated on an oversized parcel, this beau...	2 beds \| 2 baths \| 1,224 sq.ft.	$799,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.64% Airbnb Rental Income: $5754 Traditional Rental Income: $3344 Airbnb ROI: 4.34% Traditional ROI: 2.64%
79901 Overseas Highway #UNIT 204 ISLAMORADA, FL 🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best‑Kept Secret!Th...	2 beds \| 2 baths \| 981 sq.ft.	$569,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 1.37% Airbnb Rental Income: $5754 Traditional Rental Income: $3090 Airbnb ROI: 4.22% Traditional ROI: 1.37%
80450 Overseas Highway #APT 106 ISLAMORADA, FL Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse ...	2 beds \| 3 baths \| 1,303 sq.ft.	$585,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 0.62% Airbnb Rental Income: $5754 Traditional Rental Income: $3047 Airbnb ROI: 3.48% Traditional ROI: 0.62%
82779 Old Highway #UNIT 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: 0.23% Traditional cash on cash: 0.07% Airbnb Rental Income: $8621 Traditional Rental Income: $6451 Airbnb ROI: 0.23% Traditional ROI: 0.07%
82779 Old Highway #UNIT 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: 0.23% Traditional cash on cash: 0.2% Airbnb Rental Income: $8621 Traditional Rental Income: $6889 Airbnb ROI: 0.23% Traditional ROI: 0.2%
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: 2.02% Traditional cash on cash: 0.81% Airbnb Rental Income: $5754 Traditional Rental Income: $3144 Airbnb ROI: 2.02% Traditional ROI: 0.81%
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: 7.37% Traditional cash on cash: 2.28% Airbnb Rental Income: $8344 Traditional Rental Income: $3020 Airbnb ROI: 7.37% Traditional ROI: 2.28%
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.	$999,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.1% Airbnb Rental Income: $5754 Traditional Rental Income: $3271 Airbnb ROI: 3.53% Traditional ROI: 2.1%
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: 1.78% Traditional cash on cash: 0.6% Airbnb Rental Income: $5754 Traditional Rental Income: $3342 Airbnb ROI: 1.78% Traditional ROI: 0.6%
84961 Old Highway #UNIT 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: 5.67% Traditional cash on cash: 2.04% Airbnb Rental Income: $3519 Traditional Rental Income: $1498 Airbnb ROI: 5.67% Traditional ROI: 2.04%
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: 2.73% Traditional cash on cash: 0.31% Airbnb Rental Income: $8344 Traditional Rental Income: $3396 Airbnb ROI: 2.73% Traditional ROI: 0.31%
84961 Old Highway #UNIT 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: 3.02% Traditional cash on cash: 0.79% Airbnb Rental Income: $5754 Traditional Rental Income: $2537 Airbnb ROI: 3.02% Traditional ROI: 0.79%

Vacation Rentals in Islamorada

There are 35 vacation rental properties available for sale in the city of Islamorada . The median list price of Airbnb properties available for sale in Islamorada is $2,347,500 and the average price per square foot is $1,114. The cash on cash return on vacation rentals in Islamorada is 1.00%. The average monthly short term rental income in Islamorada is $5,754.

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

There are 35 Airbnb properties available for sale in Islamorada.

In April 2026, the average Airbnb occupancy rate in Islamorada is N/A%.

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

80450 Overseas Highway #UNIT 302

ISLAMORADA, FL

2 beds | 2 baths | 1,300 sq.ft.

$629,999

Airbnb cash on cash: 3.16%

Traditional cash on cash: -0.51%

Airbnb Rental Income: $5754

Traditional Rental Income: $2448

Airbnb ROI: 3.16%

Traditional ROI: -0.51%

75761 Overseas Highway

ISLAMORADA, FL

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

$4,999,900

Airbnb cash on cash: 0.05%

Traditional cash on cash: -0.35%

Airbnb Rental Income: $8621

Traditional Rental Income: $5157

Airbnb ROI: 0.05%

Traditional ROI: -0.35%

164 Venetian Dr

ISLAMORADA, FL

4 beds | 2 baths | 1,680 sq.ft.

$1,699,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $8621

Traditional Rental Income: $4408

Airbnb ROI: 2.72%

Traditional ROI: 1.08%

325 Calusa

ISLAMORADA, FL

3 beds | 3 baths | 1,619 sq.ft.

$2,300,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $6746

Traditional Rental Income: $3850

Airbnb ROI: 0.91%

Traditional ROI: 0.17%

75433 Overseas Hwy

ISLAMORADA, FL

4 beds | 4 baths | 2,624 sq.ft.

$3,999,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $8621

Traditional Rental Income: $6956

Airbnb ROI: 0.3%

Traditional ROI: 0.29%

87465 Old Hwy #102

ISLAMORADA, FL

2 beds | 2 baths | 1,032 sq.ft.

$428,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $5754

Traditional Rental Income: $3149

Airbnb ROI: 6.2%

Traditional ROI: 2.57%

79901 Overseas Higway #204

ISLAMORADA, FL

2 beds | 2 baths | N/A

$569,000

Airbnb cash on cash: 4.22%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5754

Traditional Rental Income: $3448

Airbnb ROI: 4.22%

Traditional ROI: 2.04%

126 Columbus Dr

ISLAMORADA, FL

3 beds | 3 baths | 1,786 sq.ft.

$1,499,999

Airbnb cash on cash: 3.05%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $8344

Traditional Rental Income: $4868

Airbnb ROI: 3.05%