Florida Keys Luxury Rentals - vacation rentals, private home rentals, vacation rental homes

Phone 305.852.4321
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: $9,000 - $11,000 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: $4,800 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 Oceanfront Vacation Rental Home

This 5 bedroom, 6 bath property has been recently renovated! Beautiful oceanfront location with sandy beach, fabulous heated pool, Jacuzzi, outdoor bar and pier/observation dock. Located at MM 76, Islamorada.

RATE: $7,000 Weekly   details and pictures

Tarpon Harbor

Tarpon Harbor Luxury Vacation Rental In Tavernier

Tarpon Harbor is a beautiful, luxury, oceanfront estate in the quaint little ocean side town of Tavernier. There are 3 bedrooms in the main house and an efficiency bedroom above the garage. Gated, heated pool, dock, hot tub........and a breathless, unobstructed ocean view

RATE: $25,000 Monthly  details and pictures  

Coastal Bay

Vacation Rental Home In The Florida Keys

Professionally Decorated, Breathtaking Sunsets, Featured in Florida Architect Magazine.....Welcome to "COASTAL BAY". Located in a small, exclusive, gated, Bay front community at MM 97.

RATE: $22,000 - $25,000 Monthly  details and pictures

Blue Dolphin

Blue Dolphin Luxury Vacation Rental In Islamorada

Beautiful Gated Oceanfront Estate located on 2 acres in Islamorada featuring amazing ocean views. 5 Bedrooms, 3 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees.

RATE: $4,800 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  

San Roc


San Roc 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: $4,600 Weekly 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...



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 - 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: $5,000 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

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