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 |
|---|---|---|---|
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: -0.26%
|
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: -1%
|
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: 0.82%
|
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. |
$645,000 |
Airbnb cash on cash: 7.79%
|
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. |
$2,290,000 |
Airbnb cash on cash: -1.58%
|
80201 Overseas HighwayISLAMORADA, FLExperience Islamorada living at its absolute finest with this remodeled oceanfront estate.... |
5 beds | 6 baths | 4,764 sq.ft. |
$7,800,000 |
Airbnb cash on cash: -1.19%
|
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. |
$6,500,000 |
Airbnb cash on cash: -0.12%
|
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: 3.51%
|
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: 3.43%
|
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: 3.24%
|
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: 0.37%
|
81906 Overseas Highway #UNIT 2ISLAMORADA, FLPerfectly 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: 0.43%
|
104 Anglers WayISLAMORADA, FLExclusive 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%
|
82207 Old HighwayISLAMORADA, FLGround-level living in the heart of Islamorada! Situated on an oversized parcel, this beau... |
2 beds | 2 baths | 1,224 sq.ft. |
$798,500 |
Airbnb cash on cash: 2.7%
|
102 Anglers WayISLAMORADA, FLANGLERS 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%
|
79901 Overseas Highway #UNIT 204ISLAMORADA, FL🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best-Kept Secret!This bea... |
2 beds | 2 baths | 981 sq.ft. |
$524,999 |
Airbnb cash on cash: 2.16%
|
84961 Old Highway #UNIT 7ISLAMORADA, FLBring 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%
|
82779 Old Highway #UNIT 14ISLAMORADA, FLThe 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: -1.63%
|
84961 Old Highway #UNIT 18ISLAMORADA, FLBeautiful 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%
|
80450 Overseas Highway #APT 106ISLAMORADA, FLSet 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: 1.24%
|
80639 Old Highway #UNIT 309ISLAMORADA, FLSet within a private gated enclave, this top-floor, corner unit captures the essence of Is... |
3 beds | 3 baths | 2,275 sq.ft. |
$2,730,000 |
Airbnb cash on cash: -0.6%
|
150 List StreetISLAMORADA, FLDiscover an extraordinary opportunity to own 34,000 square feet of prime bayfront real est... |
1 beds | 1 baths | 946 sq.ft. |
$4,900,000 |
Airbnb cash on cash: -0.32%
|
82779 Old Highway #UNIT 7ISLAMORADA, FLThe 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: -1.63%
|
82779 Old Highway #UNIT 8ISLAMORADA, FLThe 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: -1.63%
|
82779 Old Highway #UNIT 15ISLAMORADA, FLThe 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: -1.63%
|
124 S Hammock RoadISLAMORADA, FLNestled 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%
|
81801 Overseas Highway #UNIT 727ISLAMORADA, FLAttention 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%
|
33 Pen KeyISLAMORADA, FLWelcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare... |
3 beds | 4 baths | 4,537 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -26.17%
|
81801 Overseas Highway #UNIT #729ISLAMORADA, FLWelcome 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%
|
80450 Overseas Highway #UNIT 204ISLAMORADA, FLWelcome 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%
|
79901 Overseas Highway #UNIT 320ISLAMORADA, FLThe Palms of Islamorada is one of Islamorada's true sweet spots! Enjoy the oceanfront poo... |
1 beds | 2 baths | 827 sq.ft. |
$439,000 |
Airbnb cash on cash: 4.99%
|
81801 Overseas Highway #UNIT 637ISLAMORADA, FLWelcome 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%
|
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: -0.79%
|
154 Milano DriveISLAMORADA, FLWhat does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! T... |
2 beds | 2 baths | 1,110 sq.ft. |
$3,175,000 |
Airbnb cash on cash: -0.42%
|
Real Estate investment in Islamorada, FL
There are 34 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,450,000 and the average price per square foot is $815. In May 2026, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $2,804.