Luxury Florida Beachfront Vacation Rentals in the Keys

Experience the bliss of island living when you vacation in the Florida Keys. Islamorada is one of the most popular Keys destinations, situated between the Florida Strait and Everglades National Park. The incorporated village in Monroe County is made up of six islands, including Matecumbe Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key, and Plantation Key.


Islamorada offers a unique vacation experience unlike anywhere else in the world. The laidback atmosphere, coupled with the slower pace, makes the charming village a quiet and relaxing place to stay.


The Florida Keys are known for their breathtaking scenery and Islamorada is no exception. From the lush green national parks to the white sand beaches, beauty is in every direction you turn.


Of course, there’s much more to love about vacationing in Islamorada. The people are friendly and the businesses are highly accommodating. You’ll also find some of the most delicious foods you’ve ever had. The village is known for its locally-owned restaurants that serve up fresh seafood, sophisticated New American dishes, sweet desserts, and craft beers.


Days of sun and adventure await you in the tropical paradise of Islamorada. Here are a few recommendations of where to stay, what to do, and places to visit while vacationing in the Florida Keys.

Things to Do & Places to Go in the Florida Keys

There’s never a dull moment while vacationing in the Florida Keys. Whether you want to enjoy the beautiful scenery while lounging on the beach or partake in an epic adventure in the wilderness, you’re sure to find the right activity for you. Here are some fun ideas:

1. Picnic or Beach

Consider starting your vacation off with a laidback picnic at the beach. Bring along some sandwiches, a salad, cold beverages, and sweet treats to enjoy at one of several amazing beaches in Islamorada. Anne’s Beach is one of the most popular beaches in the village, located at mile marker 73.5. This family-friendly and pet-friendly beach is perfect for sunbathing, picnicking, or splashing around in the water. There are tables and pavilions available, as well as a boardwalk. Holiday Isle Beach is another great option and can be found at mile marker 80.2. This tourist hotspot is conveniently located near many village restaurants, meaning great food and drink is never too far away. Other great beaches in Islamorada to check out include Islamorada Library Beach and Park which is fairly secluded and tourist-free, as well as Long Key State Park which offers great views of the Atlantic Ocean. Founders Park, Islamorada Library Beach, Bahia Honda, and John Pennekamp Coral Reef State Park are also amazing options.

2. Florida Keys History

The Florida Keys have a long and interesting history that dates back to the early 1500s. Vacationers can learn about the area’s rich history by visiting one of several museums in the village. The Florida Keys History & Discovery Center is a must-visit. This world-class museum features interactive exhibits that provide interesting details about the history of the islands. Guests will also find aquariums that explore the Florida Reef, corals, and invasive lionfish. The museum also houses a research library and movie theater. You’ll also want to stop at the History of Diving Museum for an afternoon of fun. This museum is dedicated to preserving important artifacts, books, antiques, photographs, documents, and other history related to diving.

3. Food & Dining

If you’re looking for great food and drink, you don’t have to go far. Islamorada is home to dozens of amazing bars and restaurants that serve diverse menus that appeal to all palates. Start with a Caribbean-inspired dish at Hungry Tarpon Restaurant at Robbie’s, an Old Key’s-style marina and fish shack that offers both indoor or bayside deck dining. If you prefer to eat while overlooking the palm-lined beach, head to Morada Bay for French cuisine and a beautiful sunset. The Tiki Bar is where you’ll find the world-famous frozen rumrunner cocktail. The open-air tiki bar overlooks the ocean and serves up amazing specialty cocktails and cheeseburgers. They are open daily for lunch and dinner. Also, don’t forget to stop into Lorelei, Kaiyo Grill & Sushi, Mangrove Mikes, and Tower of Pizza. If you’re in the mood to sample some seasonal and barrel-aged beers on draft, stop into Florida Keys Brewing Company. Located in the Morada Way Arts District, this is the Upper Keys’ first microbrewery, offering a beer garden and much more.

4. Shopping

When it comes to shopping, Islamorada has everything you’re looking for. From fashion apparel and jewelry to memorabilia and home décor, there is truly something for everyone. You’ll even find unique items, such as handcrafted art and diving equipment. Stop into the Lobster Trap Art Gift Shop and Gallery to see tropical artwork created using repurposed lobster trap frames. At the Old Road Gallery, you’ll discover eye-catching glass and ceramics. There are also walking paths just behind the shop where you’ll see peacocks. You’ll also want to make time to visit Rain Barrel Village. This collection of open-air gift shops, antique stores, art galleries, cafes, and gardens is fun to browse. You’re sure to find something to take home as a symbol of your amazing vacation.

5. Daytime Entertainment

Looking for some daytime entertainment to fill your itinerary? There’s plenty to do and see in Islamorada. Start your day at Robbie’s marina where you can hand-feed the tarpon. Robbie’s also offers kayak and paddle board rentals, boat rentals, jet ski adventures, eco tours, and much more. Next, head to Pinecrest Garden, a beautiful botanical garden with sculptures, maintained paths, and clean restrooms. Inside the gardens, families will discover a petting zoo, wicker stick maze, and splash pad for kids. Theater of the Sea is also a must-visit during the day. This popular tourist attraction is where you can swim with Atlantic bottlenose dolphins, nurse sharks, sting rays, and California sea lions. Throughout the year, Islamorada Community Entertainment (ICE) hosts cultural events and entertainment for residents of the Upper Keys. These low-cost events range from concerts to workshops.

6. Water

Water is simply a way of life in the Florida Keys. Whether you live in Islamorada or are just visiting temporarily, you’ll no doubt want to spend some time engaging in some water activities. Kayaking, kiteboarding, and stand-up paddling boarding (SUP) are just a few fun activities to try. Water sports in Islamorada offers hours upon hours of fun and excitement for families, couples, and friends looking to spend a long afternoon or an entire day on the water. There are many companies in Islamorada that make it easy to learn a new water sport safely. Consider getting lessons from Islamorada Watersports Company, Aquaholic Adventures Holiday Isle, or Islander Watersports Islamorada.

7. Diving & Snorkeling

Islamorada is an incredible destination for snorkelers or divers that want to explore the underwater world. The ocean surrounding the village is teeming with colorful coral reefs and tropical fish. From shipwrecks to mini walls, the underwater habitat in Islamorada is truly amazing. Diving charters are easy to find in Islamorada. Contact the friendly team at Islamorada Dive Center, located on Overseas Highway. Or make an appointment at Seamonkeys Divers at the Islamorada Marina. This no-stress six-pack diving adventure with a guide is available for divers at all experience levels. There are also many snorkeling opportunities in the village. Wild Dolphin Tours offers snorkeling, sightseeing, and sandbar tours with experienced guides. A Family Fun Boat Tour Company also offers these services, along with sunset cruises.

8. Nature Tours

Untouched nature is plentiful in Islamorada. Maybe you’re looking to get up close and personal with a crocodile, want to meet a dolphin, or just want to see a gentle manatee or pink flamingo. The Florida Keys are filled with countless species of creatures you won’t find anywhere else. Islamorada makes it easy to explore its expansive wilderness. Whether you prefer to stay on dry land or want to go below the water’s surface, you’ll find endless opportunities to go on epic adventures. Set off on a walking trail, explore an underwater shipwreck, or travel through the mangroves. There are several companies in Islamorada that offer these eco tours, such as Bamboo Charters, Allergic to Land Charters, AquaBlue Adventures Boat Charters & Tours, and Easy Adventures Boat Tours.

9. Offshore Fishing

Islamorada boasts the only living coral barrier reef in America, as well as more than 500 species of fish. It’s no secret why this charming Florida Keys village is world-renowned for its sport-fishing adventures. Whether you’re a novice or an expert, you’re sure to have fun discovering new saltwater gamefish. Offshore sports fishing provides vacationers with the excitement of the catch with the opportunity to take something delicious home. Choosing a fishing charter allows you to safely navigate the waters around Islamorada with the assistance of an expert captain who will put together a customized package for your group. Some great charting companies in Islamorada to consider for your upcoming offshore fishing excursion include 95FiveFishing, Florida Backcountry Fishing, Coastal Dreams Fishing, Hooligan Sportfishing, and Islamorada Backcountry & Offshore.

10. Inshore Fishing

Islamorada’s backcountry is home to many mangrove islands ranging in size from small to large. Inshore fishing, or backcountry fishing, offers tackle and fly-fishing enthusiasts the opportunity to catch a variety of gamefish while enjoying the warm weather and breathtaking scenery. There are many species to discover in the waters of Islamorada. From snook and permit to bonefish and redfish, every catch is a surprise. Tarpon fishing is also popular in the village, especially in the spring. Whether you fish on the bayside or oceanside, or head to the deeper water channels, you’re likely to discover dozens of species of fish. If you’re in search of some light tackle fishing charters, you’re in luck. Islamorada is where you’ll find dozens of charters, such as Bud N’ Mary’s, Hold Tight Charters, Ivory Keys Charters, and Singing Reel Charters.

11. Nightlife

When the sun goes down, Islamorada continues to entertain. Islamorada offers several nightlife options for guests staying in the village. Hog Heaven Sports Bar and Grill is a local hangout that’s open until 4 AM. Stop in for some hearty portions of fresh seafood, delicious BBQ, burgers, sandwiches, and more. Oceanview Inn & Sports Pub is another must-visit. This casual sports bar and grill is a favorite for both locals and tourists alike. Stop in for a drink at happy hour which spans between 4 and 7 PM Monday through Friday. If you want to check out even more nightlife destinations, South Beach, Miami is just a short drive away. South Beach is known for its wild dance clubs, boat parties, beach clubs, and epic pool parties.

12. Destination for…

There are many reasons people from all over the world travel to the Florida Keys each year. Islamorada is the perfect destination for all types of special events that you may be celebrating in your life. Perhaps you’re planning a destination wedding and want to choose a tropical retreat while remaining in the U.S. Or maybe you’re celebrating a special anniversary and want to travel to one of the most romantic places on earth. There are also other reasons to travel to the Keys, from religious celebrations and work holidays to bachelor parties and family vacations. Of course, you don’t need a reason to visit the Florida Keys. Islamorada is also the perfect destination for adults or families that just need some rest and relaxation.

Where to Stay

The right accommodations can make all the difference during your vacation. Located in the heart of Islamorada, The Maison offers 12 unique elegant, private, and world-class residences. Some of our most popular units include:

Maison Residences – Unit 101 – Beachfront

While every unit at The Maison offers guests something special, Unit 101 stands out from the rest due to its premium location. This unit offers unsurpassed views of the Atlantic Ocean, as well as an optional boat slip at the nearby marina which can be reserved for guest use.


Unit 101 contains four cozy bedrooms and four-and-a-half baths. Enter the upscale master bedroom which provides guests with easy access to a terrace where they can take in breathtaking views of the ocean. The attached master bedroom contains a soaking tub and enclosed glass shower.

Maison Residences – Unit 202 – Oceanfront

Unit 202 at Maison Residences is an oceanfront property set on meticulously-maintained landscaping with palm trees. Guests have access to 350 feet of private beach and a 155-foot day dock. A private elevator brings guests up to their vacation rental where they’ll discover a spacious, open floor plan.


Each unit at The Maison is top-of-the-line, from the gourmet kitchen to the Sub-Zero and Wolf gas appliances. Unit 202 contains four bedrooms and four-and-a-half baths, as well as a grand room and oversized living terrace with nine-foot stacked sliders that are perfect for entertaining.

Maison Residences – Unit 203 – Oceanfront

If you’re searching for a vacation rental with oceanfront views, reserve Unit 203 at The Maison. This sophisticated property offers all of the upscale features and amenities you’re looking for, including stylish bedrooms, a master bedroom with an attached master bath, a balcony, and a morning bar.


The amenities at The Maison are beyond incredible. You’ll find an 86-foot lagoon-style pool, heated jacuzzi, 350-foot white sand beach, 155-foot day dock, and private elevators that lead to the residence. All Maison residences are also safely set in a gated community.

Maison Matecumbe Vacation Rental Islamorada

Cabana Flat – Maison Matecumbe

Cabana Flat Maison Matecumbe at The Maison is a three-bedroom, two-bath oceanside rental property situated on the Atlantic side of the Overseas Highway. Guests have access to a newly built swimming pool, lush landscaping, and a nearby sandy beach where they can relax and enjoy the sun.


The flat ocean-style property is beautiful both inside and out. Guests will find a full kitchen, living room, and dining area. There are also multiple bathrooms equipped with glass-enclosed showers and deep soaking tubs. Maison Matecumbe also offers a range of amenities, such as access to a summer kitchen with gas grills.

Book Your Stay at The Maison

Islamorada is just a short drive from Miami down the scenic Overseas Highway. The village of six islands is truly a paradise for vacationers who are looking to de-stress and enjoy a slower pace of life. If you’re looking for the perfect place to stay while vacationing in Islamorada, explore the residences at The Maison. The properties of the Maison Residence Club are comprised of new architecture and boast the only four-bedroom residences of their kind in Islamorada. Interested in learning more? Contact The Maison to request more information or to schedule a private tour.


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