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

Florida Keys Luxury Properties...

Pineapple Beach

Featured Vacation Rental 

This luxurious Florida Keys vacation home is a completely remodeled 5 bedroom 5 bath with huge beach area, tiki hut/bar, pool & hot tub.

RATE: $10,000 Weekly   details and pictures

Paradise Beach

 

Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees.

RATE: $4,200-$3,800 Weekly   details and pictures

 

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

Southwind

Southwind Oceanfront Vacation Rental Home

This 5 bedroom, 6 bath property has been recently renovated! 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.southerncomfort\index.htm

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: $12,000 Monthly details and pictures  

San Rock

 

San Rock is secluded ocean front home with spectacular views of open water. Breathtaking views of the Atlantic Ocean. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acres, a secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as "Millionaires Row".

RATE: $3,500-$4,000 Weekly details and pictures

 

Latitude

  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

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...

 

Serenity

Oasis Islamorada - Beachfront Vacation Rental Home 

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

RATE: $13,000 Monthly  details and pictures

Bliss

Bliss - Luxury Vacation Rental 

Ocean Front Beach House with Spectacular Views and Private Beach ~ New Pool ~ 3 Bedrooms 2 Baths

RATE: $11,000 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: $6,500 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

Aguazul

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