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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
87465 Old Hwy #102ISLAMORADA, FLLIVE 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%
|
164 Venetian DrISLAMORADA, FL"MULTI-FAMILY DUPLEX" Welcome to your unique private mangrove front boater's retreat in Wh... |
4 beds | 2 baths | 1,680 sq.ft. |
$1,990,000 |
Airbnb cash on cash: 4.22%
|
84745 Old Highway #UNIT 8ISLAMORADA, FLPeaceful 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%
|
104 Anglers WayISLAMORADA, FLExclusive 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%
|
84745 Old Highway #UNIT 7ISLAMORADA, FLPeaceful 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%
|
84745 Old Highway #UNIT 13ISLAMORADA, FLPeaceful 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%
|
84745 Old Highway #UNIT 4ISLAMORADA, FLPeaceful 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%
|
79901 Overseas Highway #UNIT 403ISLAMORADA, 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%
|
81801 Overseas Highway #UNIT 726ISLAMORADA, FLOwn a slice of Paradise at the Legendary Cheeca Lodge Resort and Spa in Islamorada, this s... |
1 beds | 1 baths | 550 sq.ft. |
$695,000 |
Airbnb cash on cash: -1.02%
|
100 Seashore DriveISLAMORADA, FLWelcome 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%
|
82762 Overseas Highway #UNIT 3ISLAMORADA, FLOpen 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%
|
83201 Old Highway #UNIT 409ISLAMORADA, FLWelcome 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%
|
81250 Overseas Highway #UNIT 2ISLAMORADA, FLExperience 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: -0.68%
|
36 Park RoadISLAMORADA, FLStunning 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%
|
81801 Overseas Highway #UNIT 754ISLAMORADA, FLEscape 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%
|
100 List StreetISLAMORADA, FLSeeking privacy, luxury AND convenience? This custom bayfront estate built by the current ... |
3 beds | 3 baths | 3,019 sq.ft. |
$6,395,000 |
Airbnb cash on cash: -0.39%
|
82260 Overseas HighwayISLAMORADA, FLThis renovated treehouse retreat is your picture-perfect getaway or forever island home! D... |
3 beds | 3 baths | 2,314 sq.ft. |
$899,000 |
Airbnb cash on cash: 3.74%
|
130 N Hammock RoadISLAMORADA, FLIsland 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%
|
81250 Overseas Highway #UNIT 5ISLAMORADA, FLOnly 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%
|
33 Pen Key DriveISLAMORADA, FLLegacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in... |
3 beds | 3 baths | 4,537 sq.ft. |
$2,495,000 |
Airbnb cash on cash: 0.3%
|
79901 Overseas Highway #UNIT 516ISLAMORADA, FLStunning 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%
|
79901 Overseas Highway #UNIT 218ISLAMORADA, FLLowest 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%
|
82749 Old HighwayISLAMORADA, FLWelcome to a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islam... |
3 beds | 3 baths | 1,485 sq.ft. |
$7,750,000 |
Airbnb cash on cash: -0.42%
|
219 Preston StreetISLAMORADA, FLRare Downtown Islamorada Opportunity... Just steps to the ocean, sunrises and sunsets. Wa... |
4 beds | 3 baths | 1,766 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 2.46%
|
218 Matecumbe AvenueISLAMORADA, FLBuild 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%
|
83201 Old Highway #UNIT 405ISLAMORADA, FLLocation, Dockage & Private Parking. Welcome to beautiful Beacon Reef Condominium Complex.... |
2 beds | 2 baths | 1,275 sq.ft. |
$1,199,000 |
Airbnb cash on cash: 1.84%
|
102 Anglers WayISLAMORADA, FLANGLERS REEF HOME, Islamorada's Upscale Oceanfront Gated Community, This home features 2 b... |
2 beds | 3 baths | 1,376 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 2.25%
|
109 Columbus DriveISLAMORADA, FLIconic 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%
|
120 Anglers WayISLAMORADA, FLIslamorada 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%
|
75761 Overseas HighwayISLAMORADA, FLEnjoy 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%
|
80201 Overseas HighwayISLAMORADA, FLExperience Islamorada living at its absolute finest with this remodeled oceanfront estate.... |
5 beds | 6 baths | 4,764 sq.ft. |
$9,500,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Islamorada, FL
There are 31 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,599,000 and the average price per square foot is $837. In October 2025, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $2,872.