When it comes to restaurants in the Keys, Islamorada stands out—and you don’t even have to cross a bridge to find some of the best spots. From locally caught seafood and fresh French pastries to fish tacos locals rave about, here are a few of our favorite places to eat around town.
Breakfast/Coffee
- Cafe Moka — A cozy spot with a full coffee menu, fresh pastries (the almond croissants are dangerously good), delicious yogurt (trust us), and savory quiches.
- Midway Cafe & Coffee Bar — Breakfast served with an island vibe. They have a great menu filled with options for everyone, and a full coffee menu to get your day started.
Lunch
- Bad Boy Burrito & Sushi — This local favorite serves up flavorful tacos (the fresh-catch fish tacos are a must), creative specials, and burritos packed with bold flavors. They also offer fresh sushi and poke bowls that are as refreshing as they are delicious, along with unique teas and juices that pair perfectly with the flavors they serve.
Dinner
- Square Grouper — A must-visit in Islamorada with something for every mood. Downstairs, enjoy a full restaurant menu with fresh, flavorful entrees. Upstairs, the lounge offers craft cocktails and a unique tapas menu, with ceviches and desserts that are always on point.
- Chef Michael’s — Specializing in perfectly cooked dishes and the freshest local fish, Chef Michael’s is a locally owned and operated gem. The care in both quality and service shows in every bite, making it a standout for fine dining in Islamorada.
Sushi
- Sushi Sake — Menu full of fresh ingredients and something for everyone. We highly recommend the wahoo tataki as an appetizer.
- Shima — You’re going to have to cross a bridge for this one, but it is worth the short drive north to Tavernier to experience the presentation, flavors, and atmosphere.
Pizza
- Bayside Gourmet — When it comes to pizza, Bayside Gourmet is always our go-to. You really can’t go wrong with any of their pies, but the saltimbocca (especially on cauliflower crust for that thin, crispy perfection) is a top contender.
If you try any of these spots, we’d love to hear what you think. And if you’re ever looking for more local recommendations, feel free to reach out! We’re always happy to talk good food.
Why a Monthly Vacation Rental in Islamorada May Be Your Best Vacation Yet
Swap your usual morning routine for coffee with a view of turquoise waters. End your days with fresh-caught seafood, salty breezes, and one of those sunsets the Keys are famous for. In Islamorada, a monthly rental is your ticket to slowing down and truly enjoying every moment.
Why Choose a Monthly Rental in Islamorada?
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Settle In and Live Like a Local
A month in the Keys lets you sink into the rhythm of island life. You will find your favorite coffee spot (we recommend Cafe Moka), learn when the fish are biting (sorry, top secret!), and discover quiet beaches and mangrove trails that most visitors never see.
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A True Home Base
A well-equipped rental feels like a home away from home from the moment you arrive, allowing you to quickly settle in, and giving you the freedom to cook your own meals, bring your boat along, store your fishing gear, and keep your paddleboard ready to hit the water whenever you want.
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Experience More Than the Highlights
Staying for a month lets you explore beyond the usual tourist spots and discover the hidden gems where locals love to hang out.
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The Perfect Pace
With a whole month, there’s no need to cram activities into a tight schedule. Spend one day fishing offshore, another snorkeling at Alligator Reef, and another simply lounging on the porch with a book. Islamorada is best enjoyed at a slower pace.
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Space for Friends and Family
With a monthly rental, there’s plenty of time and space for friends or family to visit.
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Weather That Never Gets Old
Spending a month in Islamorada means waking up to the kind of weather that feels just right every single day. Not too hot, not too cool, just steady sunshine and refreshing breezes.
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Ideal for Remote Work
If you can work from anywhere, why not make that “anywhere” a porch with a view of the beach? Our rentals have reliable Wi-Fi and comfy spots to get your work done, so you can mix business with plenty of relaxation.
Things to Do During Your Month in Islamorada
- Fishing & Boating – Charter a boat for world-class deep-sea or backcountry fishing.
- Water Adventures – Kayak through mangroves, snorkel coral reefs, or paddleboard along calm bays.
- Local Dining – Enjoy fresh, local seafood at favorites like Square Grouper or Chef Michaels.
- Art & Culture – Visit the History of Diving Museum or browse local art galleries and boutiques in the Morada Way Art District.
- Day Trips – Head south to explore Key West or north to enjoy Key Largo’s famous John Pennekamp Coral Reef State Park.
Why Book with a Professional Local Property Manager?
When you rent with a trusted local manager, you get more than just a home, you get peace of mind and a team that’s here to help whenever you need us. At Solace Properties, our monthly rentals in Islamorada and the Upper Keys are well-maintained, comfortably furnished, and ready for you to settle in. Since we live locally, we’re always available to answer your questions and share our favorite spots to eat, explore, and enjoy. We handle the details so you can focus on making the most of your time in paradise.
Whether you’re seeking a change of scenery, an extended getaway, or a season of island living, a month in paradise could be your most memorable trip yet.