OCEAN SIDE VACATION RENTALS FLORIDA KEYS

Southern Comfort Islamorada – Brand New $18-20,000 Monthly, call for holidays

Southern Comfort Islamorada – Brand New

$18-20,000 Monthly, call for holidays

Wide ocean views from every room in this gated, monthly rented beachfront estate, aptly named ‘Southern Comfort’. Vacation comfortably in this 3 bedroom, 3.5 bath, immaculately kept home. Sprawling grounds on the 1/2 acre estate lead to a heated pool and over 80′ of private…

3 beds 3.5 baths

Maison Residences – Unit 102 – Beachfront $12,000-16,000 Weekly - Call for Summer deals and Holiday rates

Maison Residences – Unit 102 – Beachfront

$12,000-16,000 Weekly - Call for Summer deals and Holiday rates
Maison Residences offers world-class oceanfront residences in the Florida Keys. Unit 102 at Maison Residences is a luxurious property offering sweeping views of the Atlantic Ocean from the kitchen, grand room, master bedroom, and oversized living terraces. The residence is clean, stylish, and offers all...
4 beds 4.5 baths

Maison Residences – Unit 101 – Beachfront $12,000-16,000 Weekly - Call for Summer deals and Holiday rates

Maison Residences – Unit 101 – Beachfront

$12,000-16,000 Weekly - Call for Summer deals and Holiday rates
Introducing Maison Residences 101... Islamorada, also known as “Village of Islands” or the “Fishing Capital of the World,” is a village of six islands located approximately 90 minutes south of Miami. The popular vacation destination boasts a wide range of activities, from the Theater of...
4 beds 4.5 baths

Maison Residences – Unit 402 – Oceanfront & Pool Front $9,500-11,500 weekly call for holiday rates

Maison Residences – Unit 402 – Oceanfront & Pool Front

$9,500-11,500 weekly call for holiday rates
Introducing Maison Residences 402... Planning a vacation to the Florida Keys? Consider a stay in Islamorada, a village comprised of six of the Florida Keys, located halfway between Key West and Miami. Islamorada is known for its coral reefs, rich history, and lavish accommodations. Where...
3 beds 3.5 baths

Maison Residences – Unit 403 – Oceanfront & Pool Front $9,500-11,500 weekly call for holiday rates

Maison Residences – Unit 403 – Oceanfront & Pool Front

$9,500-11,500 weekly call for holiday rates
Introducing Maison Residences 403... Planning a vacation to the Florida Keys? Consider a stay in Islamorada, a village comprised of six of the Florida Keys, located halfway between Key West and Miami. Islamorada is known for its coral reefs, rich history, and lavish accommodations. Where...
3 beds 3.5 baths

Maison Residences – Unit 203 – Oceanfront Price is in Property Description

Maison Residences – Unit 203 – Oceanfront

Price is in Property Description
$10-12,500 WEEKLY FALL SEASON $15,000 WEEKLY RENTAL SEASON Please call for holiday rates Introducing Maison Residences 203... Nestled between the turquoise waters of the Florida Strait and the wilderness of Everglades National Park is Islamorada. The quaint village of Islamorada is made up of six...
4 beds 4.5 baths

Maison Residences – Unit 202 – Oceanfront Price is in Property Description

Maison Residences – Unit 202 – Oceanfront

Price is in Property Description
$10-12,500 WEEKLY FALL SEASON $15,000 WEEKLY RENTAL SEASON Please call for holiday rates UP TO 32’ BOAT SLIP MAY BE AVAILABLE Introducing Maison Residences 202... There’s nothing quite like vacationing in the Florida Keys. The warm weather, sunny skies, and tropical environment create the ultimate...
4 beds 4.5 baths

Tea Table Key Private Island Estate and Wedding Venue $25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

Tea Table Key Private Island Estate and Wedding Venue

$25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

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

6 beds 5 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.

[vc_video link='https://www.youtube.com/watch?v=o0jYKUSoVlY']

Oceanfront Beach Cottages

4 beds 3 baths

The Beach House $10,000 Weekly - Call for holiday rates

The Beach House

$10,000 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

Green Turtle Beach $11,500 -$14,500, Call for Holiday Rates

Green Turtle Beach

$11,500 -$14,500, 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

Maison Residences – Unit 201 – Oceanfront Price is in Property Description

Maison Residences – Unit 201 – Oceanfront

Price is in Property Description

$10-12,500 WEEKLY FALL SEASON $15,000 WEEKLY RENTAL SEASON Please call for holiday rates   Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — A world-class oceanfront residence, located in the heart of Islamorada in the Florida…

4 beds 4.5 baths

Maison Residences – Unit 204 – Oceanfront Price is in Property Description

Maison Residences – Unit 204 – Oceanfront

Price is in Property Description

$10-12,500 WEEKLY FALL SEASON $15,000 WEEKLY RENTAL SEASON Please call for holiday rates   Introducing Maison Residences Unit 204, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — A world-class oceanfront residence, located in the heart of Islamorada in the Florida…

4 beds 4.5 baths

Ishmael’s Watch $20,000 / Monthly Call for Holiday rates

Ishmael’s Watch

$20,000 / Monthly Call for Holiday rates

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.   Six 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…

6 beds 4 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

Ocean Terrace Currently Under Construction

Ocean Terrace

Currently Under Construction

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. Currently Under Construction Vacation Rental License #VR-047.  

3 beds 3 baths

Seaside Breezes $18,000-$20,000 Monthly

Seaside Breezes

$18,000-$20,000 Monthly

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 enjoys it… Enjoy mornings on the wrap around patio watching…

3 beds 2 baths

Angler’s Reef Garden Side W/ Dockage $2400 / Weekly call for holiday and Monthly rates

Angler’s Reef Garden Side W/ Dockage

$2400 / Weekly call for holiday and Monthly rates

MM 85. 2 Bedroom & 2.5 Bath. Two spacious bedrooms and two and a half bath, sleeps six. Enjoy the Beautiful garden views and ocean breezes from these island-style villas or relax poolside. Nestled amidst quaint streets and walking paths, their design takes inspiration from…

2 beds 2.5 baths

Sunrise – Maison Matecumbe $5,000/ weekly - Call for holiday rates

Sunrise – Maison Matecumbe

$5,000/ weekly - Call for holiday rates

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

Cabana Flat – Maison Matecumbe – Oceanfront $5,500/ weekly - Call for holiday rates

Cabana Flat – Maison Matecumbe – Oceanfront

$5,500/ weekly - Call for holiday rates
Introducing Maison Matecumbe Cabana Flat Just off the southern Florida Keys between Key West and Key Largo is Islamorada, a small village comprised of five islands. The popular vacation destination features more than 17 miles of paradise complete with mouthwatering cuisine, epic adventures, and an...
3 beds 2 baths

Reservation Procedure

A 30% security deposit is required along with the rental agreement and application within 24 hours to insure your booking.  The security deposit is payable by credit card.  A $75.00 reservation fee, cleaning fee and 12.5% sales and county tax are additional to the rental amount.  The balance due is payable by check or wire transfer within 90 days prior to check in  Cancellations will be refunded in full 90 days prior to check in.  The 30% security deposit will be refunded within 30 days after your departure if the property is found in satisfactory condition.  

 

Please be advised that during the event of a hurricane, your deposit is fully refundable without penalty. You may also use your deposit toward a future rental at a different date.

 

Status of properties and prices are subject to change. If owner changes status of property, a substitution will be made or refund given. Check-in is 4 PM. Check-out is 10 AM.

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