Luxury Beachfront Vacation Rentals in the Florida Keys

Islamorada is a quaint village located just 90 minutes south of Miami. This little slice of paradise is known for its coral reef, dolphin encounters, and historic ruins from the 1800s. With so much to do, see, and experience, it’s clear why Islamorada has become one of the most popular vacation destinations in the world.


With its warm sunshine, tepid temperatures, and lush scenery, Islamorada provides the perfect setting for a tropical getaway. The village has a relaxed vibe that encourages visitors to let go of their worries and indulge in the natural beauty of the Florida Keys.


When comparing beachfront vacation rentals in Islamorada, Florida Keys, you’ll come across both oceanside and bayside properties. Both options provide guests with spectacular views, making either choice a win-win. The biggest difference between the two pertains to the sun. Oceanside vacation rentals deliver breathtaking sunrises, while bayside vacation rentals are beloved for their sunsets.


For the very best in beachfront luxury vacation rentals, Island Villa reigns supreme. Island Villa is a trusted source for Islamorada vacation rentals, having served the Florida Keys for more than 15 years. Choose from beautiful ocean rentals, bay rentals, canal rentals, or condo and flat rentals. Island Villa also offers the most stunning ocean backdrops for major events like weddings.


At Island Villa Properties, guests can enjoy privacy in a quiet and luxury environment. Envision yourself lounging in a hammock as the cool ocean breeze sweeps across your skin or soaking in a bubbling hot tub that overlooks the expansive shoreline. Island Villa’s beachfront vacation rentals are also in close proximity to many of the area’s best activities and attractions.

Start Planning Your Luxury Beachfront Vacation Rental in Islamorada

Island Villa is dedicated to helping you find the best beachfront vacation rental in Islamorada. The tropical village of Islamorada is a haven for anglers in search of the perfect catch, couples celebrating their union, or families looking to make memories. View our extensive selection of luxury Florida Keys rentals and start planning the vacation of a lifetime.

Contact us at 305.664.3333 or so we may help with your Florida Keys rental plans

Maison Residences – Unit 101 – Beachfront

Maison Residences includes a group of world-class oceanfront residences situated in the heart of Islamorada. Unit 101 is a beachfront villa surrounded by manicured grounds and a resort-style pool and jacuzzi area. The flat ocean side style property features four bedrooms and four-and-a-half baths and is available as a weekly rental. 


Take a private elevator up just one floor where you’ll find a private entrance to your villa. You’ll be welcomed with a bright, airy floor plan, gourmet kitchen equipped with top-of-the-line appliances, and a spacious grand room. A living terrace offers multiple seating areas, a fireplace, large flat-screen TV, and a Lynx infrared/gas grill. 

Maison-Residences-Islamroada Florida Keys

Maison Residences – Unit 403 – Oceanfront & Pool Front

Just a brief 90-minute drive from Miami, this Maison Residence offers all the comforts of home with the luxuries you’d find in a sophisticated resort. Unit 403 is a flat ocean side vacation rental with three bedrooms and three-and-a-half baths. It is safely located in a gated residence and features 10’ ceilings, porcelain tile, and a balcony that overlooks the pool and ocean.


While staying at Maison Residences, honeymooners have access to a wide range of lavish amenities, including a 86’ lagoon-style pool, heated jacuzzi, 155’ day dock, and 350’ of white sand beach. The third bedroom in the unit is an ‘in-law’ suite that features a separate entrance from the elevator, a full bath, balcony, king-size bed, and morning bar. Unit 403 at Maison Residences is the perfect destination for romantic getaways.

Maison Residences – Unit 202 – Oceanfront

Unit 202 is an oceanfront villa at Maison Residences with four bedrooms and four-and-a-half baths. The flat ocean side vacation rental is fully equipped with everything you need for a relaxing and romantic honeymoon, including a spacious floor plan, gourmet kitchen, and beautiful grand room that opens up to an oversized living terrace with 9’ stacked sliders. The master bedroom also offers terrace access, as well as ocean and pool views.


This beachfront destination comes with a range of luxury amenities, including a Nest front door bell camera, smart front door locks, in-ceiling speakers, Caesar-stone countertops, private elevators, and access to a heated jacuzzi and 86’ lagoon-style pool. A 32’ boat slip may also be available upon request. Maison Residences can be found conveniently located just off the Old Road near the Arts and Culture District of Islamorada.

Maison Residences – Unit 203 – Oceanfront

This next luxurious residence is an oceanfront property that offers many of the same luxury amenities as other Maison Residences. Unit 203 is located in a gated residence with access to a pool and heated jacuzzi. Enjoy sweeping views of the ocean and more than 350’ of the white sand beach from your private balcony. Inside, the villa offers flat-screen TVs in every bedroom, 10’ ceilings, porcelain tile, Caesar-stone countertops, U-Line beverage center, and Sub-Zero and Wolf gas kitchen appliances.


From the Kohler plumbing fixtures to the designer-selected lighting fixtures, the vacation rental offers charming accommodations for honeymooners. The villa contains four cozy bedrooms and four-and-a-half baths. While guests are not lounging indoors, they can enjoy the sprawling, palm tree filled beach or take a stroll down the 155’ day dock as the tide rolls in. Maison Residences are also centrally located in Islamorada, making it easy to see the local sights and attractions with minimal travel.

Cabana Flat – Maison Matecumbe

Beautiful honeymoon vacation rentals are not hard to find if you know where to look. Within the charming Maison Matecumbe gated community, you’ll find a spectacular unit known as Sunrise. The luxury accommodation has three bedrooms and three baths. The flat ocean side villa also offers spectacular views of the sprawling pool, ocean, and tropical trees.


Maison Matecumbe is a small, nine-unit condo located at mile marker 81 just off the Old Road in Islamorada. The property has a newly built pool and hot tub, as well as a sandy beach. Dockage may also be obtainable through the Islamorada Marina by contacting the marina directly for rates. For couples that value their privacy but desire cozy, lavish amenities and spectacular ocean views, the Maison Matecumbe Sunrise unit is the ultimate honeymoon vacation rental.


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

Top Activities and Attractions in Islamorada

There’s never a dull moment while vacationing in the Florida Keys. Islamorada offers a little something for everyone, whether you’re traveling as a family, couple, or solo. Get up close and personal with a dolphin at the Theater of the Sea or explore the small islands and coral reef near Islamorada via kayak. Children will enjoy feeding the tarpon at Robbie’s Marina or splashing in the clear, turquoise waters at Anne’s Beach.

World Famous Restaurants in Islamorada

Sampling the diverse cuisine is one of the best parts of staying in Islamorada. With ample access to shrimp, grouper, dolphin, yellowtail snapper, and more, Islamorada restaurants serve fresh seafood daily at establishments like Twisted Shrimp and Chef Michael’s.


If you’re looking for something else to treat your palate, you’ll find American favorites, vegetarian-friendly options, and tasty treats at restaurants like Bayside Gourmet, Tower of Pizza, and Midway Café & Coffee Bar.