Featured Florida Keys Vacation Rentals
Pineapple Beach
5 Bedrooms / 5 Baths
RATE: $10,000 – $12,000 Weekly
Pineapple Beach is a luxurious ocean front Florida Keys vacation home with 5 bedroom 5 bath with huge beach area, tiki hut/bar, pool & hot tub. Sleeps 10, Mile Marker 88.5 Oceanside, Islamorada
Southern Comfort
6 Bedrooms / 6.5 Baths
RATE: $6,000 – $7,500 Weekly
Southern Comfort is the perfect vacation home in the Florida Keys, located on the ocean at MM 77 in Islamorada. This very private Estate sits on 3+ acres offering 6 bedrooms and 6.5 baths.
Southwind
5 Bedrooms / 6 Baths
RATE: $8,000 – $8,500 Weekly
This is a stunning 5 bedroom, 6 bathroom vacation home in Islamorada. Southwind is Ocean Front with a private beach, heated pool, Jacuzzi, out door bar and pier/observation deck. The gourmet kitchen would impress any chef. The unobstructed ocean views at Southwind are breathtaking.
Turtle Nest Estate
4 Bedrooms / 4.5 Baths
RATE: $4,000 – $6,000 weekly
This luxurious oceanfront estate is located in Islamorada at Mile Marker 76. 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.
Paradise Beach
4 Bedrooms / 4 Baths
RATE: $5,100 Weekly
Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate… Paradise Beach. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees.
Blue Dolphin
5 Bedrooms / 4 Baths
RATE: $5,200 Weekly
Beautiful Gated Oceanfront Estate located on 2 acres in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, winding staircase, expansive ocean views, Over 4000 Sq. Ft. of Living Space. Heated pool, sandy back yard, gated entrance lined with palm trees.
Kara-Pan
5 Bedrooms / 7 Baths
RATE: $9,950 Weekly
Kara-Pan 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.
San Roc
4 Bedrooms / 3 Baths
RATE: $3,900 – $4,800 Weekly
San Roc is secluded ocean front home with spectacular 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”
Bay Beach
4 Bedrooms / 4 Baths
RATE: $25,000 Monthly
This gorgeous Florida Keys Luxury Rental Home features 4 bedrooms and 4 baths, a Bayfront pool, sandy beach and dockage
Bay Breeze
4 Bedrooms / 4 Baths
RATE: $25,000 Monthly
Enjoy expansive bay views at Bay Breeze, a 4 bedroom vacation rental home with dockage and fantastic waterfront swimming pool
Lime Key
3 Bedrooms / 2 Baths
RATE: $9,500 Monthly
It’s all about the view……and the Lime Key vacation rental home has that breathtaking view. This beautiful Key Largo home features 3 bedrooms and 2 baths. Enjoy the Keys beautiful weather while sunning by the bay front heated pool. This property also has an exterior elevator for your convenience.
Coastal Bay
3 Bedrooms / 4.5 Baths
RATE: $22,000 – $25,000 Monthly
Coastal Bay is a 3 Bedroom 4.5 Bath Waterfront home with Dock, Pool, Jacuzzi, & Beach. 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.
Tarpon Harbor
4 Bedrooms / 5.5 Baths
RATE: $25,000 Monthly
Tarpon Harbor is a beautiful Luxury Florida Keys rental located in the quaint ocean side town of Tavernier. This 4 bedroom oceanfront vacation home offers a gated entrance, gorgeous heated pool, dock, hot tub, plenty of outdoor seating……..and a breathless, unobstructed view of the Atlantic Ocean.
Paradise Pointe
4 Bedrooms / 3 Baths
RATE: $14,000 Monthly
The Paradise Pointe is located in iconic Key Largo. This Florida Keys Luxury Rental home offers 4 bedrooms 3 baths, a private beach, heated pool, Jacuzzi, Kayaks, Paddle Board and boat dock with a view of John Pennekamp State Park marine sanctuary waters. Conveniently located at mile marker 102, ocean side.
Angler’s Bay
4 Bedrooms / 4.5 Baths
RATE: $22,000 Monthly
Angler’s Bay luxury Florida Keys vacation rental home is a 4 bedroom, 4.5 bath Bayfront estate that offers a gorgeous bayfront pool and Jacuzzi, 40ft dock, kayaks, paddle boards and magnificent Florida Keys sunsets. Located on peaceful Long Key in Islamorada.
Latitude
4 Bedrooms / 3 Baths
RATE: $18,000 Monthly
Latitude: Freedom of thought or action. No word could better describe this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool or fish from the pier. Latitude boasts 2 master suites and two guest rooms.
Serenity
3 Bedrooms / 3 Baths
RATE: $13,000 Monthly
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.
Keys Comfort
3 Bedrooms / 3 Baths
RATE: $5,000 Monthly
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. Keys Comfort also provides a protected dock for your boating needs.