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: -1%
|
81250 Overseas Highway #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: 0.87%
|
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%
|
81250 Overseas Highway #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: -0.18%
|
80201 Overseas HighwayISLAMORADA, FLExperience Islamorada living at its absolute finest with this remodeled oceanfront estate.... |
5 beds | 6 baths | 4,764 sq.ft. |
$7,400,000 |
Airbnb cash on cash: -1.2%
|
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. |
$6,900,000 |
Airbnb cash on cash: -0.17%
|
189 Carroll StreetISLAMORADA, FLNewly 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%
|
191 Carroll StreetISLAMORADA, FLNewly 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%
|
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 #2ISLAMORADA, FLPerfectly 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%
|
79901 Overseas Highway #204ISLAMORADA, FLSpectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed ... |
2 beds | 2 baths | 981 sq.ft. |
$469,000 |
Airbnb cash on cash: 2.53%
|
82779 Old Highway #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%
|
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 #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 #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 #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 #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 #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 #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 #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. |
$615,000 |
Airbnb cash on cash: 1.33%
|
81801 Overseas Highway #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%
|
143 N Hammock RoadISLAMORADA, FLExperience 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%
|
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%
|
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%
|
84961 Old Highway #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%
|
84961 Old Highway #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%
|
84961 Old Highway lot: 27ISLAMORADA, FLMemories 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%
|
84961 Old Highway #41ISLAMORADA, FLISLAMORADA 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%
|
316 N DrISLAMORADA, FLSimply the best location, exclusive & extremely private. It's tucked away in the prestigio... |
3 beds | 4 baths | N/A |
$2,500,000 |
Airbnb cash on cash: 0.65%
|
164 Venetian DrISLAMORADA, FLBoaterâs dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home... |
4 beds | 2 baths | 1,680 sq.ft. |
$1,549,000 |
Airbnb cash on cash: 0.38%
|
79901 Overseas Higway #204ISLAMORADA, FLSpectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed... |
2 beds | 2 baths | N/A |
$469,000 |
Airbnb cash on cash: 2.53%
|
87200 Overseas Hwy #K5ISLAMORADA, FLDiscover the Florida Keys lifestyle at Executive Bay Club Unit K5, one of Islamoradaâs h... |
3 beds | 2 baths | 1,352 sq.ft. |
$685,000 |
Airbnb cash on cash: 5.12%
|
87851 Old Highway #M5ISLAMORADA, FLA New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has... |
2 beds | 2 baths | 1,732 sq.ft. |
$1,300,000 |
Airbnb cash on cash: 1%
|
81801 Overseas Highway #714ISLAMORADA, FLOceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income p... |
1 beds | 1 baths | 550 sq.ft. |
$710,000 |
Airbnb cash on cash: 3.82%
|
Real Estate investment in Islamorada, FL
There are 43 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,334,202 and the average price per square foot is $759. In July 2026, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $2,821.