Picking the Best Luxury Florida Vacation Rentals in the Keys

The Florida Keys are one of the most popular vacation destinations in the world, offering the perfect combination of warm weather, sandy beaches, and fun attractions. This island paradise is also where you’ll find a wide range of luxury vacation rentals.


Maybe you’re looking for a spacious beach house with an oceanfront pool. Or perhaps you want a bayfront property that offers dockage and unobstructed sunset views. Regardless of what you’re looking for, you’re sure to find the luxury vacation home of your dreams in the Florida Keys.


With so many options to choose from, it can be hard to narrow it down to just one. Check out these tips for picking the best luxury Florida vacation rental in the Keys.

Things to Consider for Your Next Vacation Rental

Establish Your Priorities

When it comes to planning a luxury vacation, you don’t want to settle for less. However, there may be some things that you want to prioritize over other things, such as the property’s proximity to the beach. Make a list of what features you require in a vacation rental and which you can do without.


Carefully Read the Description

The description of a vacation rental can tell you a lot about what you can expect when you arrive. A good description should clearly describe the property both inside and out. It should list the key features and amenities and discuss why someone might want to rent the home for a getaway experience.


Look at the Number of Rooms

If you’re traveling with your family or a group, you’ll want to pay close attention to the size of the property. Choose a property that offers enough bedrooms for each guest to prevent some guests from having to sleep on the sofa. The property should also have multiple bathrooms to give each guest their privacy.

Evaluate the Kitchen

While you probably didn’t go on vacation to cook, having a fully-equipped kitchen is more important than you think. It can become very costly to eat out for every meal, especially in the Florida Keys. Opt for a kitchen that features top-of-the-line appliances and premium materials, such as porcelain tile and Caesar-stone countertops.


Cozy Furnishings

Whether you’re spending days, weeks, or even months in the Florida Keys, you’ll want to ensure that your rental is as homey as possible. Choose a vacation rental that contains a variety of comfortable seating options, such as soft sofas and plush mattresses. The home should also have adequate dining areas.


View Photos and Videos

You don’t want to rent a luxury Florida vacation home sight unseen. Take the time to look through the available photos and videos, if available, to ensure that the property matches the description. Steer clear of vacation rentals that do not provide any photos or videos.

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

Search Luxury Florida Keys Vacation Rentals

Islamorada is home to some of the most charming vacation rentals in the Keys. Explore the wide selection of luxury vacation rentals from Island Villa Properties to find your little piece of paradise.

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 rentals@islandvilla.com 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.