Honeymoon Vacation Rentals in Islamorada Florida Keys

Beautiful Islamorada offers honeymooners a luxurious escape

Where tasty cuisine, remarkable sights, and fun adventures await – Located just 90 minutes south of Miami, FL. Islamorada is the perfect destination for a laidback vacation. Its small-town vibe, coupled with its turquoise water, stunning sunrises, and myriad of attractions, makes it the ideal location for a romantic honeymoon.

Located at the southern tip of the continental U.S., the Keys is known for its year-round Caribbean-like weather. Sunny skies and warm temps are almost always in the forecast, especially during Florida’s dry season which runs from December through April. Islamorada offers couples an exotic experience without the exorbitant price tag of traveling to a tropical country.

Accommodations in the Florida Keys range from Airbnbs to 5-star hotels. Private, quiet villas are the optimal choice for honeymooners in search of cozy interiors, premium amenities, and easy access to local attractions. Skip the cramped hotel rooms and costly resorts in favor of a spacious and affordable villa conveniently located near the best restaurants, shopping, sights, and activities in the Keys.

Choosing a place to temporarily call home during your honeymoon can be tough and you certainly don’t want to regret your decision later on. Whether you’re planning a leisurely vacation spent lounging at the beach or a fast-paced adventure snorkeling in a diverse underwater ecosystem, you’ll want an intimate luxury vacation rental to return to at the end of a long day.

Where to Stay in Islamorada, Florida Keys

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 – 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.

Call (305) 664-3333

Things to Do in Islamorada, Florida Keys

Known as the ‘Sportfishing Capital of the World’, Islamorada is a diverse village with an abundance of things to do and see. This lavish destination accommodates all types of travelers, whether you’re a foodie, history buff, adventurer, or just looking for relaxation. Leave your troubles behind and partake in some of these fun activities and attractions:

World Famous Restaurants in the Florida Keys

Breakfast: Start your morning at Mangrove Mike’s Café, located on Overseas Highway. The self-acclaimed “Best Restaurant in Islamorada, FL” is popular with the locals, offering an informal breakfast and lunch-only dining menu. Enjoy mouthwatering options like cinnamon apple hotcakes, Belgian waffles, eggs benedict, and their famous breakfast tater tot towers.

Dinner: When dinner time arrives, head to Chef Michael’s for a meal consisting of upscale seafood and New American entrees served island-style. Start with a plate of conch chowder or escargot Florentine, followed by an entrée of roast duck, mango, mandarin oranges and cashews, vegetables, and coconut rice.

Delivery: Don’t want to leave the comfort of your vacation rental? Don’t worry; delivery is just a phone call away. Located in the heart of Islamorada, Tower of Pizza offers some of the best eats in the Upper Florida Keys. Choose from a selection of appetizers like shrimp cocktail or mozzarella sticks. You’ll also find subs, wings, calzones, strombolis, desserts, and of course, delicious pizzas.

Florida Keys Adventures

Take a Day Trip to Key West: Key West is a popular tourist attraction chocked full of things to do and see. Choose a weekday to avoid the crowds and traffic and check out all the top tourist attractions, such as the Ernest Hemingway Home and Museum or the Key West Butterfly and Nature Conservatory.

Grab a Local Craft Brew: Sample some of the local craft brew made with fresh ingredients from around the Keys. Try the food and beverage offerings at Islamorada Brewery & Distillery or hang out in the beer garden at the Florida Keys Brewing Company.

Charter a Fishing Boat: Experience sports fishing at its best when you charter a fishing boat from Blue Heaven Charter. Stock up on fresh fish that you can enjoy eating the rest of the week.

Feed Tarpon at Robbie’s: You’ve probably seen it on TV and now you have the opportunity to partake in this fun activity yourself. Drop a fish into a school of more than 100 tarpons that gather around Robbie’s Marina waiting for humans to toss them a tasty treat.

Snorkel to See the Sights: Go on a snorkel adventure in John Pennekamp Coral Reef State Park. The park has remnants of an early Spanish shipwreck approximately 100 feet from the beach, as well as the Christ of the Abyss statue. You can also see the reef from a glass-bottom boat tour.

Rentals in the Florida Keys

Kayak, Bike, or Paddle: While in Islamorada, head out for a day of fun. Outdoor enthusiasts will find everything they need to kayak, bike, or paddle with rentals from Backcountry Cowboy Outfitters. Partake in a guided eco-tour on land or water, no prior experience is needed.

Watersports & Boat Rentals: At A1A Watersports & Boat Rentals, honeymooners will discover a wide range of activities and services, including jet ski island tours, boat rentals, wave runner freedom rides, diving, snorkeling, and paddleboarding.