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Florida Keys Luxury Rentals - Your Source For Upscale Vacation Properties In The Upper Keys

Florida Keys Luxury Properties...

Turtle Nest Estate


This luxurious new oceanfront estate is located in Islamorada. Enjoy the island's year-round sunny weather on the home's exotic wood deck surrounding a custom pool - all overlooking a private sugar sand beach on the Atlantic Ocean. New observation pier!

RATE: $4,000 - $6,000 Weekly   details and pictures

The Gardens

Featured Vacation Rental 

The Gardens is a 4/4 private home surrounded by impeccably landscaped grounds. This property has over 50 types of palms, abundant orchids, and bougainvilleas. At your doorstep is a breathtaking view of the Atlantic Ocean where you can experience endless aquatic activities.

RATE: $5,500 Weekly   details and pictures


Southwind Oceanfront Vacation Rental Home

This 5 bedroom, 6 bath property is currently undergoing renovations and will be available in 2016! Beautiful oceanfront location with fabulous pool and dock. Located at MM 76, Islamorada.

RATE: $7,000 Weekly   details and pictures  

Southern Comfort

Southern Comfort Oceanfront Vacation Rental Home

Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean… and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres offering 5 bedrooms and 5.5 baths.

RATE: $6,500 Weekly   details and pictures  

Karapan I


Karapan I is a beautiful, spacious, private, plantation-style estate home on 5 acres. It is located at Mile Marker 81.5 in the heart of Islamorada and boasting 5 bedrooms and 7 baths. Heated pool, Jacuzzi, sandy beach, all with a spectacular open-water views.

RATE: $8,950 Weekly details and pictures  

Paradise Pointe


This 4 bedroom/3 bath home offers direct access to many of the John Pennekamp State park kayak trails and the Atlantic Ocean. Located at mile marker 102 ocean side…..Paradise Pointe is a keys vacation you will not forget.

RATE: $14,000 Monthly details and pictures  


  Latitude Oceanfront Luxury Vacation Rental

Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and two guest rooms.

RATE: $18,000 Monthly   details and pictures  

Pineapple Plantation

Pineapple Plantation Luxury Vacation Rental In Islamorada

Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada.

RATE: $21,000 Monthly  details and pictures  


Nautica Luxury Vacation Rental In Islamorada

Nautica has stunning views of the crystal clear bay waters of Islamorada, with a heated swimming pool and boat dockage that can fit up to a 30' boat.

RATE: $20,000 Monthly  details and pictures  



Florida Keys Modest Properties...

Bamboo Beach

Our most affordable oceanfront, beach, and pool home. This popular home is located in south Islamorada. We may just have what you've been dreaming about.

RATE: $4,000 Weekly  details and pictures



Oasis Islamorada - Beachfront Vacation Rental Home 

Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably.

RATE: $12,000 Monthly  details and pictures

Keys Comfort

Vacation Rental Home 

Keys Comfort is a 3 Bedroom/3 Bath newly remodeled Canal Front Home. Keys Comfort is what you will enjoy at this beautiful Islamorada property.

RATE: $4,500 Monthly  details and pictures


Blue Harbor

Vacation Rental Home  Vacation Rental Home

This private ocean front home in Islamorada offers 4 bedrooms and 3 baths. Enjoy beautiful ocean views from the kitchen, dining, bar and living room. It is one of the few rental properties with a fully screened porch.

RATE: $2,500 Weekly  details and pictures


Vacation Rental Home In The Florida Keys

Aguazul is located at Mile Marker 88, in beautiful Islamorada. This gorgeous four bedroom/three bath home will sleep 8 people very comfortably.

RATE: $4,500 Weekly  details and pictures



Our vacation rental inventory includes only the best properties the Upper Florida Keys have to offer.  We will do everything to make your luxury vacation relaxing and comfortable.

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Questions or Comments? Contact
Jo Anne Thibeau ~ Property Manager ~ Phone 305.852.4321 ~ Fax 888-519-1981