Peace of Paradise $20,000 / monthly

Peace of Paradise

$20,000 / monthly

MM 75. Four bedrooms/three and a half baths. Gorgeous house over 3 floors, with heated/cooled pool in quiet, private side street in Lower Matecumbe Key. Directly on the Atlantic with open 180-degree panoramic view. Upscale interior design, fully furnished. Glass elevator. Gorgeous views from every…

4 beds 3.5 baths
4 beds 3.5 baths

Seaside Breezes $4,500/ weekly

Seaside Breezes

$4,500/ weekly

Mile Marker 94. Three bedrooms/two baths.   Ocean front in South Key Largo– this private gated home has dockage and is known for the soft breezes & beautiful sunrises.   Enjoy the Atlantic Ocean how a local sees it…  Comfortably sleeps 6.        Monthly.  

3 beds 2 baths
3 beds 2 baths

Ocean Terrace $4,500 weekly - $15,000 monthly

Ocean Terrace

$4,500 weekly - $15,000 monthly

Mile Marker 81.5, This 3 bedroom, 3 bath home is complete with den, breezes and sunrises.   Featuring a jacuzzi and splash pool located right next to the sandy beach, this home comfortable sleeps 6-8 people. Vacation Rental License #VR-047.  

3 beds 3 baths
3 beds 3 baths

The Beach House $7,000 - $9,000 Weekly - Call for holiday rates

The Beach House

$7,000 - $9,000 Weekly - Call for holiday rates

Mile Marker 80 – Oceanfront Indulge in the island lifestyle at this beautiful private estate located in the heart of Islamorada. The gated property is lush in tropical landscaping that boost an oceanfront pool, boat dockage, brand NEW tennis court and sand volleyball net. Enjoy…

4 beds 4 baths
4 beds 4 baths

Sea Ranch $9,000 weekly ~ Call for holiday rates

Sea Ranch

$9,000 weekly ~ Call for holiday rates

Mile Marker 83 – Oceanfront

Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada!  This stunning property is truly a tropical paradise with a private, sandy beach and observing pier.  Relax at the beach or cool down in the beachside pool.

The front home sits waterfront with 1 bedroom 1 bath upstairs, and a separate 1 bedroom 1 bath downstairs.  Downstairs is great for entertaining with a pool table, wet bar, poker table and more.

The garden cottage sits back on the property with two bedrooms and one bathroom and is just a walk through the sandy garden away from the ocean front house.

The ocean front paradise is also a ‘Destination/Wedding Location!’

$9,000/week –  Call for Holiday Rates.

The viewing dock is just that, it is too shallow for boats so boats are prohibited. But great for light flats fishing, catch small flats fish or pitch a kayak out. We do have information on nearby marinas for dockage.

Please note, the Pool is heated to 88 degrees and does NOT have a hot tub.   The side pool is a spa with jets.

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Oceanfront Beach Cottages

4 beds 3 baths
4 beds 3 baths

Green Turtle Beach $10,500 -$12,500, Call for Holiday Rates

Green Turtle Beach

$10,500 -$12,500, Call for Holiday Rates

Mile Marker 81. Ocean front estate with five bedrooms, five & a half baths.   One of the most ultra-luxurious properties in Islamorada, Green Turtle Beach features an immaculately manicured 4 acres of ocean front land.   Catch ocean breezes off the multiple porches and balconies at…

5 beds 5.5 baths
5 beds 5.5 baths

Oasis At Tavernier $20,000 Monthly ~ Call for Holiday Rates

Oasis At Tavernier

$20,000 Monthly ~ Call for Holiday Rates

$20,000 monthly~ Call for holiday rates   Mile Marker 92.   This luxurious 6 bedroom estate is located in Tavernier, in the Upper Florida Keys. Conveniently located a short distance from the Atlantic Ocean, deep water dockage makes Oasis in Tavernier perfect for boaters.  …

6 beds 7 baths
6 beds 7 baths

Angler’s Reef Garden Side $2,600 / weekly

Angler’s Reef Garden Side

$2,600 / weekly

MM 85. 2 Bedroom & 2.5 Bath. Located on the quiet side of Angler’s Reef Village. A walk down quaint streets to pool, ocean and beach!

2 beds 2.5 baths
2 beds 2.5 baths

Ishmael’s Watch $18,000-$20,000 / monthly

Ishmael’s Watch

$18,000-$20,000 / monthly

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.   Seven bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade…

7 beds 4 baths
7 beds 4 baths

Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates

Grey Heron Cottage

$6,500 Weekly ~ Call for holiday rates

Mile Marker 89 – Oceanfront   Grey Heron Cottage Estate (named after original owner) is located on the famous Millionaire’s Row. You’ll love the fantastic sun rises, ocean views, dockage and brand new pool that this property features!   After entering the gated grounds, a…

3 beds 2.5 baths
3 beds 2.5 baths

Leila’s Beach House $4,750 / weekly

Leila’s Beach House

$4,750 / weekly

Miles Marker 81 – Oceanfront   Cozy, stylish house located in the heart of Islamorada.  3 Bedrooms and 2 baths located right on the ocean with a heated pool, private beach and more!  Enjoy the large master bedroom with master bath and shower.  Located at…

3 beds 2 baths
3 beds 2 baths

Moon Rise is a spectacular unit within Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81.   Newly done pool  and Hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy…

3 beds 3 baths
3 beds 3 baths

Sunrise is a spectacular unit within the Maison Matecumbe gated community.  Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy…

3 beds 3 baths
3 beds 3 baths

Unit 301 located within Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental…

3 beds 2 baths
3 beds 2 baths

Introducing Maison Residences…   A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys.   This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just…

4 beds 4.5 baths
4 beds 4.5 baths