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 |
|---|---|---|---|
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: 0.24%
|
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%
|
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%
|
84961 Old Highway #UNIT 21ISLAMORADA, FLStunning Ocean Views in Islamorada - the Fishing Capital of the World!Enjoy panoramic view... |
2 beds | 2 baths | 946 sq.ft. |
$1,399,000 |
Airbnb cash on cash: 2.56%
|
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 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%
|
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. |
$1,999,999 |
Airbnb cash on cash: 3.82%
|
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. |
$1,600,000 |
Airbnb cash on cash: 5.97%
|
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%
|
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. |
$710,000 |
Airbnb cash on cash: 5.31%
|
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. |
$2,600,000 |
Airbnb cash on cash: 1.66%
|
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: 0.28%
|
80201 Overseas HighwayISLAMORADA, FLExperience Islamorada living at its absolute finest with this remodeled oceanfront estate.... |
5 beds | 6 baths | 4,764 sq.ft. |
$8,100,000 |
Airbnb cash on cash: N/A
|
79901 Overseas Highway #UNIT 218ISLAMORADA, FLLET'S MAKET A DEAL! Seller has just reduced this condo by $50,000. At this price, this up... |
1 beds | 2 baths | 827 sq.ft. |
$399,900 |
Airbnb cash on cash: 4.69%
|
82749 Old HighwayISLAMORADA, FLWelcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old H... |
3 beds | 3 baths | 1,485 sq.ft. |
$7,499,000 |
Airbnb cash on cash: -0.4%
|
83201 Old Highway #UNIT 405ISLAMORADA, FLUnparalleled amenities are what seperates Beacon Reef condo complex from any other complex... |
2 beds | 2 baths | 1,275 sq.ft. |
$1,199,000 |
Airbnb cash on cash: 1.84%
|
189 Carroll StreetISLAMORADA, FLNewly 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: 2.55%
|
191 Carroll StreetISLAMORADA, FLNewly 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: 2.47%
|
80909 Old HighwayISLAMORADA, FLExcellent price adjustment and ready for you to fall in love!! Premier Islamorada location... |
4 beds | 3 baths | 1,562 sq.ft. |
$2,900,000 |
Airbnb cash on cash: 2.05%
|
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. |
$999,000 |
Airbnb cash on cash: 1.64%
|
32 Park RoadISLAMORADA, FLIdeally 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: 2.32%
|
100 List StreetISLAMORADA, FLIslamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada wit... |
3 beds | 3 baths | 3,019 sq.ft. |
$5,900,000 |
Airbnb cash on cash: -0.34%
|
219 Preston StreetISLAMORADA, FLBack on market with Huge Price Improvement! Rare Downtown Islamorada Opportunity... Just s... |
4 beds | 2 baths | 1,766 sq.ft. |
$990,000 |
Airbnb cash on cash: 3.37%
|
83201 Old Highway #UNIT 301ISLAMORADA, FLBeacon Reef is calling your name! This beautifully designed 2-bedroom, 2-bath residence s... |
2 beds | 2 baths | 1,275 sq.ft. |
$895,000 |
Airbnb cash on cash: 2.28%
|
81906 Overseas Highway #UNIT 3ISLAMORADA, FLWelcome 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: -0.06%
|
83201 Old Highway #UNIT 504ISLAMORADA, FLExclusive 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: 1.71%
|
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%
|
74501 Overseas HighwayISLAMORADA, FLDiscover coastal luxury at its finest in this stunning oceanfront estate -- the very last ... |
5 beds | 4 baths | 3,772 sq.ft. |
$4,900,000 |
Airbnb cash on cash: N/A
|
141 El Capitan DriveISLAMORADA, FLStunning Waterfront Oasis in Port Antigua Welcome to your dream home in the Florida Keys-a... |
4 beds | 3 baths | 2,098 sq.ft. |
$2,650,000 |
Airbnb cash on cash: 3.11%
|
316 N DrISLAMORADA, FLSimply the best location, exclusive & extremely private. It's tucked away in the prestigio... |
3 beds | 4 baths | N/A |
$2,750,000 |
Airbnb cash on cash: 0.06%
|
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%
|
126 Columbus DrISLAMORADA, FLFlorida Keys waterfront home, offered fully furnished, 1,786 SqFt living area (larger than... |
3 beds | 3 baths | 1,786 sq.ft. |
$1,499,999 |
Airbnb cash on cash: 1.66%
|
164 Venetian DrISLAMORADA, FLBoaterâs dream in White Marlin Beach, Islamorada! Unique 2-story single-family home with... |
4 beds | 2 baths | 1,680 sq.ft. |
$1,990,000 |
Airbnb cash on cash: 4.22%
|
236 Costa Bravo DrISLAMORADA, FLA rare architectural masterpiece by renowned architect Max Strang, this modern coastal est... |
5 beds | 8 baths | 6,367 sq.ft. |
$14,900,000 |
Airbnb cash on cash: N/A
|
325 CalusaISLAMORADA, FLThis 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: 0.64%
|
75433 Overseas HwyISLAMORADA, FLSandy Beach Cove â A Luxurious Island Retreat Nestled in the heart of Islamorada, Sandy ... |
4 beds | 4 baths | 2,624 sq.ft. |
$4,189,000 |
Airbnb cash on cash: 1.21%
|
439 Palm Drive DriveISLAMORADA, FLExperience refined waterfront living in the Florida Keys, where luxury meets effortless ac... |
3 beds | 3 baths | 2,294 sq.ft. |
$2,650,000 |
Airbnb cash on cash: 0.31%
|
114 Spoonbill RoadISLAMORADA, FLNewly renovated 3-bedroom, 2-bath canal-front CBS home with direct bay access. The interio... |
3 beds | 2 baths | 1,232 sq.ft. |
$2,300,000 |
Airbnb cash on cash: 0.64%
|
Real Estate investment in Islamorada, FL
There are 42 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,795,000 and the average price per square foot is $872. In December 2025, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $2,872.