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%
|
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. |
$1,900,000 |
Airbnb cash on cash: 4.08%
|
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%
|
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%
|
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%
|
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%
|
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%
|
100 List StISLAMORADA, FLIslamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada wit... |
3 beds | 3 baths | 3,019 sq.ft. |
$5,800,000 |
Airbnb cash on cash: -0.33%
|
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. |
$850,000 |
Airbnb cash on cash: 2.45%
|
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%
|
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: -0.05%
|
20 Park RdISLAMORADA, FLDowntown Islamorada gem located on a massive 11,000+ square-foot lot on a quiet street. Va... |
2 beds | 2 baths | 1,120 sq.ft. |
$899,000 |
Airbnb cash on cash: 4.17%
|
19 Avacado StreetISLAMORADA, FLSituated bayfront on an expansive 1.27-acre parcel, this striking contemporary residence c... |
5 beds | 7 baths | 5,489 sq.ft. |
$12,950,000 |
Airbnb cash on cash: N/A
|
82207 Old HwyISLAMORADA, FLGround-level living in the heart of Islamorada! Situated on an oversized parcel, this beau... |
2 beds | 2 baths | 1,224 sq.ft. |
$849,000 |
Airbnb cash on cash: 4.28%
|
33 Pen Key DriveISLAMORADA, FLWelcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare... |
3 beds | 4 baths | 4,537 sq.ft. |
$2,495,000 |
Airbnb cash on cash: -23.63%
|
79901 Overseas Highway #UNIT 204ISLAMORADA, FL🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best‑Kept Secret!Th... |
2 beds | 2 baths | 981 sq.ft. |
$590,000 |
Airbnb cash on cash: 4.75%
|
104 Anglers WayISLAMORADA, FL****This home is currently rented & no Available for showing until 04/02/2026****Exclusive... |
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. |
$1,295,000 |
Airbnb cash on cash: 2.84%
|
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%
|
102 Anglers WayISLAMORADA, FLANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community, T... |
2 beds | 3 baths | 1,376 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 2.15%
|
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%
|
126 Columbus DrLower Matecumbe, 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: 1.67%
|
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 HwyLower Matecumbe, 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%
|
87465 Old Hwy #102ISLAMORADA, FLLIVE THE DREAM IN THIS OCEANFRONT BUILDING IN THE BEAUTIFUL FLORIDA KEYS! LARGER THAN OTHE... |
2 beds | 2 baths | 1,032 sq.ft. |
$428,000 |
Airbnb cash on cash: 7.18%
|
79901 Overseas Higway #204ISLAMORADA, FLSpectacular Direct Ocean Views! ? Islamorada's Best-Kept Secret! This beautifully appointe... |
2 beds | 2 baths | N/A |
$590,000 |
Airbnb cash on cash: 4.75%
|
82779 Old Highway #UNIT 17ISLAMORADA, 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: 1.88%
|
Real Estate investment in Islamorada, FL
There are 42 properties for sale in the city of Islamorada . The median list price in Islamorada is $1,550,000 and the average price per square foot is $709. In February 2026, the average monthly cash on cash return in Islamorada is N/A%. The average monthly rental income in Islamorada is $2,813.