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 |
|---|---|---|---|
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: 4.14%
|
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: -0.36%
|
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. |
$1,550,000 |
Airbnb cash on cash: 2.02%
|
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: N/A
|
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: 2.45%
|
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: 2.37%
|
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: 0.38%
|
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. |
$550,000 |
Airbnb cash on cash: 2.23%
|
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: -1.09%
|
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. |
$4,499,500 |
Airbnb cash on cash: -0.62%
|
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. |
$4,000,000 |
Airbnb cash on cash: -1.15%
|
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. |
$4,000,000 |
Airbnb cash on cash: -1.15%
|
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: -1.16%
|
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: -1.36%
|
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: -26.77%
|
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: -1.09%
|
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. |
$595,000 |
Airbnb cash on cash: 2.2%
|
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. |
$715,000 |
Airbnb cash on cash: -1.11%
|
81801 Overseas Highway #716ISLAMORADA, FLExquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your u... |
1 beds | 1 baths | 358 sq.ft. |
$549,500 |
Airbnb cash on cash: 2.45%
|
81801 Overseas Highway #715ISLAMORADA, FLExquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your u... |
1 beds | 1 baths | 358 sq.ft. |
$549,500 |
Airbnb cash on cash: 2.45%
|
81801 Old Highway #754ISLAMORADA, FLCrystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect... |
1 beds | 1 baths | 550 sq.ft. |
$649,000 |
Airbnb cash on cash: 1.83%
|
81250 Overseas Highway #2ISLAMORADA, FLRefined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This... |
3 beds | 3 baths | 2,072 sq.ft. |
$2,485,000 |
Airbnb cash on cash: 0.59%
|
82779 Old Highway #1ISLAMORADA, FLVilla 1 offers one of the most coveted locations within the exclusive 22-villa community a... |
4 beds | 5 baths | 2,574 sq.ft. |
$4,750,000 |
Airbnb cash on cash: -0.67%
|
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: 2.42%
|
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: 1.37%
|
84961 Old Highway #18ISLAMORADA, FLBeautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept... |
2 beds | 2 baths | 793 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.53%
|
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: 1.12%
|
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: 3.54%
|
84961 Old Highway #A1ISLAMORADA, FLCharming concrete bungalow in the heart of Islamorada! Move right into this beautifully up... |
1 beds | 1 baths | 406 sq.ft. |
$439,000 |
Airbnb cash on cash: 3.6%
|
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. |
$4,750,000 |
Airbnb cash on cash: -0.41%
|
84961 Old Hwy 17 HwyISLAMORADA, FLEscape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath... |
1 beds | 1 baths | N/A |
$298,000 |
Airbnb cash on cash: 5.81%
|
87200 Overseas Hwy #K5ISLAMORADA, FLDiscover the Florida Keys lifestyle at Executive Bay Club Unit K5, one of Islamorada's hid... |
3 beds | 2 baths | 1,352 sq.ft. |
$685,000 |
Airbnb cash on cash: 3.2%
|
107 Valencia DrISLAMORADA, FLOCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete ho... |
3 beds | 3 baths | 1,632 sq.ft. |
$2,500,000 |
Airbnb cash on cash: 0.36%
|
74049 Overseas HwyISLAMORADA, FLRare opportunity to own an ocean side single family home in the heart of Islamorada. Situa... |
4 beds | 4 baths | 2,596 sq.ft. |
$3,850,000 |
Airbnb cash on cash: -0.32%
|
316 N DrISLAMORADA, FLSimply the best location, exclusive & extremely private. It's tucked away in the prestigio... |
3 beds | 4 baths | N/A |
$2,400,000 |
Airbnb cash on cash: 0.16%
|
102 Venetian DrISLAMORADA, FLBoaters paradise in Isla Morada Florida the Sport Fishing Capital of the World, this 3 bed... |
3 beds | 2 baths | 1,380 sq.ft. |
$1,600,000 |
Airbnb cash on cash: 1.43%
|
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: 1.57%
|
Real Estate investment in Islamorada, FL
There are 42 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,259,167 and the average price per square foot is $771. In October 2026, the average monthly cash on cash return in Islamorada is -1.00%. The average monthly rental income in Islamorada is $2,435.