Local’s Guide to Islamorada: Best Hotels, Food, & Things to Do

Islamorada is one of my favorite spots to hang out in the Florida Keys. After living here for over a decade, it’s clear that the bohemian yet upscale vibe of Islamorada makes it unlike anywhere else. With several collections of little boutiques, breweries, and craft studios, Islamorada is a true haven for artists (and shoppers!).

Islamorada is also known as the “Sportfishing Capital of the World,” making it a great spot for the guys who love heading out early to reel in the big one. With its turquoise waters, luxury resorts, and refined dining scene, Islamorada is the perfect choice for travelers who want to relax in style.

Here’s your guide to the best hotels, restaurants, and attractions in Islamorada. This article is part of my complete Florida Keys travel guide, where I share itineraries, island guides, and essential tips for planning your Keys vacation.

Best Hotels in Islamorada

Cheeca Lodge & Spa

With 27 acres of tropical gardens, a nine-hole golf course, and a 525-foot fishing pier, Cheeca is pure luxury. Guests can enjoy a full-service spa, three on-site restaurants, and oceanfront pools. Rooms and suites have private balconies, soaking tubs, and sweeping ocean views. For food, don’t miss Atlantic’s Edge, serving Caribbean-inspired seafood with locally sourced ingredients.

The Islands of Islamorada

Perfect for families, The Islands of Islamorada offers multi-bedroom villas and plenty of on-site activities. It is also great for boaters and Florida locals because it is possible to reserve dockage. Other activities will keep you busy without ever having to leave the resort, like pickleball, yoga, kayaking, paddle boarding, and a pool with a hot tub to unwind in after a fun day in the Keys

Amara Cay Resort

A boutique, eco-conscious resort with a modern coastal design. Amara Cay offers ocean views, hammocks strung between palms, and complimentary kayaks and paddleboards. The pool deck is just the place to unwind after a day on the ocean, and the on-site ReelCatch restaurant offers live music Thursday thru Saturday.

Islander Resort

Perfect for families, Islander Resort sits on 24 oceanfront acres with two saltwater pools, a true beach, volleyball courts, and a mix of villas and suites. Guests love the casual beachside vibe and activities like snorkeling, paddleboarding, and fishing excursions arranged right from the resort.

Three Waters Resort

After a multimillion dollar facelift, the Three Waters Resort has just reopened. The property features three distinct pools and two moderate stretches of beach. Guests rave about the rooftop sunset bar (happy hour!), which offers panoramic views of the Atlantic, as well as the sea-to-table dining experiences, and Starbucks on-site.

The tiki bar here is also said to be the first tiki bar in Islamorada and where the Rum Runner cocktail was invented in 1969. It’s a great choice for travelers who want a contemporary, stylish stay with plenty of amenities.

The Moorings Village

This resort is a collection of villas tucked away into a grove of palm trees by the water, providing an oasis for guests. The privacy here is unmatched, with only eight cottages across 11 acres of waterfront. The Moorings is a family run establishment that provides beachfront luxury in one of the best locations in Islamorada.

For more help planning your trip, visit my Florida Keys travel guide to explore island comparisons and sample itineraries.

Where to Eat in Islamorada

Islamorada has a thriving food scene, mixing laid-back island favorites with upscale fine dining overlooking the ocean. Whether you’re after freshly caught seafood or a perfectly grilled steak, here are some can’t-miss spots:

• Morada Bay Beach Café – Famous for its full moon parties, this beachfront café serves fresh seafood and cocktails in a relaxed, toes-in-the-sand atmosphere.
• Pierre’s – A more upscale sister restaurant to Morada Bay, Pierre’s offers fine dining with a French-Caribbean flair. Signature dishes include yellowtail snapper meunière and duck breast with rum glaze.
• Lazy Days – A waterfront staple serving generous portions of seafood. The Lazy Days style preparation (fish topped with tomatoes, onions, and key lime butter) is legendary.
• Chef Michael’s – A local institution for upscale seafood with a creative twist. Their hogfish, prepared in several unique styles, is considered one of the best dishes in the Keys.
• Kaiyo Grill – A stylish sushi and wood-grill spot blending island flavors with Asian influence.
• MEAT Eatery & Taproom – Featured on Diners, Drive-Ins, and Dives, MEAT is a casual, no-frills spot famous for inventive burgers and craft beer. Here everything is homemade, down to the sauces!
• Papa Joe’s Waterfront – A laid-back eatery with marina views, serving comfort-style seafood dishes and plenty of local charm.
• Ziggie & Mad Dog’s – A legendary Islamorada steakhouse where hearty portions and old-school atmosphere meet expertly prepared cuts of meat.

Skip the hassle of looking for flights! Use my Award Booking Concierge Service. I’ll find the flights on points and let you know exactly how to book. 

Where to Drink in Islamorada

The nightlife here is relaxed and beachy, often with live music and stunning views. These are some of the best spots to grab a drink:

• Florida Keys Brewing Co. – A colorful, locally owned brewery with tropical-inspired craft beers like the Honey Hibiscus Kolsch.
• Lorelei Restaurant & Cabana Bar – Known for live music and one of the best sunset views in the Keys. My favorite there is the frozen key lime colada.
• Hog Heaven – A classic Keys waterfront dive bar that transforms into a lively late-night scene. Known for strong drinks, bar food, and a mix of locals and visitors.
• The Whistle Stop Pub – One of Islamorada’s oldest watering holes, this no-frills dive is a favorite for cheap drinks and a friendly, Keys-style atmosphere.
• Islamorada Brewery & Distillery – A local craft favorite offering beers brewed on-site plus small-batch spirits. Great for a casual afternoon tasting.

Things to Do in Islamorada

Islamorada is all about the water, wildlife, and relaxed luxury. Here are the highlights:

• Fishing Charters – Islamorada earned its nickname because of its world-class sportfishing. You can book offshore charters for mahi-mahi, sailfish, and tuna, or backcountry trips for tarpon and snook.
• Theater of the Sea – A family-friendly attraction where visitors can swim with dolphins, sea lions, and even stingrays. It’s one of the oldest marine mammal parks in the U.S.
• History of Diving Museum – A fascinating collection of artifacts showcasing the history of diving, from ancient helmets to modern scuba gear.
• Robbie’s Marina – Famous for hand-feeding massive tarpon right from the docks. It also has an open-air market, art stalls, and boat rentals. If you just want to feed the tarpon, then I suggest Bud n’Mary’s Marina, so you aren’t attacked by pelicans.
• Founders Park– For a nominal entrance fee you can use the beach and other facilities at this park. Check out the events calendar to see what is coming up during your stay, as there are often festivals or musical performances here.
• Keys History & Discovery Center– Get an understanding of how the Keys developed through short films and modern displays. You can also get acquainted with all the local fish in their aquarium. This little museum sure packs a lot in! Located at the Islander Resort.

Pros & Cons of Staying in Islamorada

Pros	Cons
Luxury resorts with a boutique feel	More expensive than Key Largo or Marathon
Excellent dining and craft cocktails	Limited nightlife compared to Key West
Some of the best fishing in the world	Small beaches (but gorgeous views)
Central location for exploring the Upper and Middle Keys

Bottom Line: Who Should Stay in Islamorada

Stay in Islamorada if you’re looking for a luxury island escape with fine dining, boutique resorts, and unique water experiences. It’s perfect for couples, foodies, and anyone who wants a quieter Keys vacation with a touch of elegance.

If you prefer looking for more budget or family-friendly options, then see my Key Largo guide. For those focused on the best fishing and snorkeling, be sure to visit Marathon. Key West has the best options for bar-hopping, pirate history, and excursions. If you want to work your way through the Keys over a week, rather than cram one spot into a weekend, then copy my one week Florida Keys itinerary.

Ready to plan your full itinerary? Explore my complete Florida Keys travel guide for everything you need to know before you go.