Upper Keys Vacation Rentals

From Key Largo to Marathon, the Upper Keys are a popular refuge for travelers. The islands of the Upper and Middle Keys consist of limestone and form a long narrow arc. This unique configuration derives from an ancient tidal-bar system where tidal channels cut through a submerged oolitic deposit. Visitors will discover that these bars are still exposed on the islands and that the channels between the bars separate the islands.


Along with a fascinating history, the Upper Florida Keys has a lot to offer. Each year, millions are drawn to the Keys due to its laidback town vibe, beautiful blue-green water, incredible seafood options, and awe-inspiring sunrises. Villages in the Upper Keys, such as Islamorada, offer plenty of things to do and see, such as museums, state parks, nature conservatories, and brewing companies. The Upper Keys is also a stunning location for weddings and honeymoons.


While staying in the Upper Keys, consider a luxury vacation rental that provides direct access to the beach and ocean. At Island Villa Properties, you’ll find a wide variety of beachfront, oceanfront, and seaside luxury vacation rentals.

Upper Keys Vacation Rentals

If you’re looking for a private, quiet, and luxury experience featuring all the amenities you’d expect to see in a five-star resort, then reserve a vacation property from Island Villa Properties.

Contact us at 305.664.3333 or rentals@islandvilla.com so we may help with your Florida Keys rental plans

Island Villa’s Maison Featured Properties

One of the biggest decisions you will need to make when planning a trip to the Florida Keys is where you’ll stay. There is no shortage of incredible resorts, hotels, and other rental properties in the Keys but not all will offer the features you’re looking for. Island Villa’s Maison properties are unique in that they offer luxury accommodations, resort-style amenities, and everything you need for a safe, comfortable, and upscale vacation.


Here’s a look at some of Island Villa’s featured properties in the Florida Keys:

Maison Residences – Unit 101 – Beachfront

Maison Unit 101 is a beachfront residence featuring four spacious bedrooms and four-and-a-half baths. This luxury property is open, bright, and welcoming with its large windows that overlook the Atlantic Ocean. Inside the property, guests will discover a gourmet kitchen with top-of-the-line appliances, a grand room, a master bedroom, and oversized living terraces.


Outside, the manicured grounds have tropical palm trees, paved sitting areas, and a white sand beach. In the center of the property sits a lavish 86-foot lagoon-style swimming pool and heated jacuzzi. Enjoy the warm weather and scenic views while lounging poolside or cooling off in the water.

Maison Residences – Unit 202 – Oceanfront

Unit 202 at Maison Residences is a four-bedroom, four-and-a-half-bath oceanfront property. Take a private elevator to the villa which is equipped with Nest front doorbell cameras and smart front door locks. Once inside, you’ll find 10-foot ceilings, Caesar-stone countertops, porcelain tile, and designer-selected light fixtures.


No expense has been spared when designing this Upper Keys luxury vacation rental. From the Lynx infrared/propane grill on the terrace to the on-site 155-foot day dock, each amenity has been carefully selected to ensure that guests have a smooth and relaxing vacation. Maison Residences is also centrally located near some excellent restaurants, exciting tours, and other fun adventures.

Maison Residences – Unit 203 – Oceanfront

Staying at Maison Residences means getting to choose from multiple amazing luxury properties. Unit 203 at Maison is a four-bedroom, four-and-a-half-bath rental that provides guests with beautiful ocean views and countless amenities. The gated residence is just a 90-minute drive from Miami, or travelers can touch down in the bay with a seaplane.


Maison 203 is equipped with everything you’ll need for a relaxing vacation, such as access to a swimming pool and heated jacuzzi, a 350-foot white sand beach, a 155-foot day dock, and flat-screen TVs in every bedroom. The spacious living terraces provide guests with even more space to relax and entertain.

Cabana Flat – Maison Matecumbe

If you’re looking to stay oceanside while visiting Islamorada, look no further than Maison Matecumbe. Maison Matecumbe is a small gated community featuring nine cozy units. Guests will find these luxury vacation condos at mile marker 81, just off the old road in Islamorada.


There’s much to love about Maison Matecumbe, from its newly completed swimming pool to the nearby sandy beach. Guests also have access to a hot tub, outdoor dining and lounge areas, cozy living spaces, and spectacular views of the ocean. Dockage may also be available through the Islamorada Marina.


Contact us at 305.664.3333 or rentals@islandvilla.com so we may help with your Florida Keys rental plans.