Where to Stay in Islamorada (COOLEST Areas!)

FIRST TIME IN ISLAMORADA

FIRST TIME IN ISLAMORADA

Upper Matecumbe Key

Right in the heart of Islamorada, Upper Matecumbe Key is a great base for exploring the region from. For this reason, we recommend it as our top choice for first-time visitors.

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FOR COUPLES

FOR COUPLES

Lower Matecumbe Key

The final island within the Islamorada chain, Lower Matecumbe Key has an even more peaceful atmosphere. This island is also more adult than the others, making it our top pick for couples in the region.

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FOR FAMILIES

FOR FAMILIES

Plantation Key

Plantation Key is the largest island in the region and the perfect spot for families heading to Islamorada. In the south of the island, you will find Rain Barrel Village, a local creative commune that is a true haven for artsy types.

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Islamorada is stretched across numerous islands, so you’ll need to bring or hire a car to get the full experience. There’s a large bridge connecting all the islands, with the mainland in one direction and Key West in the other. It takes around two and a half hours to drive from one end of the Florida Keys to the other, with Islamorada located roughly in the middle.

Plantation Key is the first island you’ll discover when driving through Islamorada from the mainland. For families, this island offers peaceful vibes alongside family-friendly attractions. With laid-back theme parks and a wide variety of restaurants, you’ll be spoiled for choice on Plantation Key. It’s also known as the creative heart of the Florida Keys, with art communes and galleries found everywhere. For the purpose of this guide, we’ve included Windley Key with this area, as they’re both well connected.

Heading further along the road, you will hit Upper Matecumbe Key. This island is a little bit livelier (though still peaceful by any other standard) than Plantation Key, offering first time visitors the chance to really explore the region. It’s also the most central area of Islamorada, so you’ll be well placed for exploring the region throughout your stay.

Finally, we have Lower Matecumbe Key. There’s no avoiding how expensive the Florida Keys are, but if you really want to stick to a budget, you’ll have better chances in Lower Matecumbe Key. While this is the quietest island, it’s also home to some of the best bargains on accommodation. The food isn’t too bad either, and it’s a great spot for couples.

Still undecided? It’s a tricky choice to make, but we’ve got some more advice about each area below to help you narrow down your options. We’ve included our top picks for where to stay in Islamorada, and things to do in each to make your planning that little bit easier.

1. Upper Matecumbe Key – Best Place to Stay in Islamorada for Your First Time

Upper Matecumbe Key is right in the heart of Islamorada, so it’s a great base for exploring the region from and our top choice for first-time visitors. With marvelous views and a bustling entertainment district, you’ll have plenty of things to do on this island.

When we say bustling, though, we mean in comparison to the rest of the area. Upper Matecumbe Key has plenty of peaceful spots to relax and soak up the chilled out Florida vibes. The restaurants here are known for their sunset views, making this a great spot for couples heading on a romantic break to Islamorada.

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Top Things to Do in Upper Matecumbe

1. We can’t get enough of the sunset views from the restaurants here – Islamorada Fish Company offers a great menu and sunset shark feedings.
2. The Keys History & Discover Centre offers fantastic exhibits detailing the history and culture of this beautiful region.
3. Unwind among the mangroves at Library Beach Park – there are also some barbecue facilities available to use free of charge.
4. Fishing is a popular activity in the area, and we recommend going with 4reel Fishings Charters for your boat and equipment.

Luxurious Retreat in Upper Matecumbe: The Russell Estate

This gorgeous home right on the coast is the perfect retreat if you don’t want to leave the villa too often. The outdoor space includes a private pier where you can enjoy some fishing, or launch the available kayak into the ocean for an afternoon paddle. It’s also surrounded by restaurants and marinas where you can soak up the laid back Islamorada vibes.

Peaceful Hideaway in Upper Matecumbe: Houseboat

You won’t get better ocean views than this! Stay on your own private houseboat just off the coast of Upper Matecumbe for a truly unique experience. The boat is fully solar and wind-powered, meaning it’s also our top pick for environmentally conscious travelers in Islamorada. Kayaks are also available if you want to do some exploring. Please be aware that you can’t stray too far from the coast.

Luxury Hotel in Upper Matecumbe: Cheeca Lodge & Spa

When it comes to upscale resorts, it doesn’t get any better than this vast coastal resort in Upper Matecumbe! Surrounded by verdant gardens and a beautiful ocean, you’ll get to enjoy your own slice of paradise at Cheeca Lodge & Spa. This is a bit of a splurge property, but totally worth it if you want next-level service. The on-site spa is also the perfect place to let your stresses melt away.

2. Lower Matecumbe Key – Where to Stay in Islamorada for Couples

The final island within the Islamorada chain, Lower Matecumbe Key has an even more peaceful atmosphere. This island is also more ‘adult’ than the others, making it our top pick for couples visiting the region. You’ll get to enjoy fancy restaurants and some gorgeous sunset views.

It’s also marginally the most affordable island. You’ll still have to careful if you’re travelling on a budget, but there are plenty of great deals on accommodation here. This is especially true during the offseason, so keep this in mind when planning a winter getaway.

Top Things to Do in Lower Matecumbe

1. Habanos Oceanfront Dining has casual vibes, gorgeous views, and a simply unmissable Cuban food and drinks menu.
2. White Marlin Beach Park is the main beach on the island, offering laid-back vibes and secluded spots where you can soak up the sea breeze without the big crowds.
3. Head to Saltwater Fly Guide, which offers some of the most affordable fishing charter options in the Florida Keys.

Peaceful Beach House in Lower Matecumbe: Islamorada Escape

Enjoy a romantic getaway right on the beach in this charming villa. The marina is within walking distance, so you’ll be close to all the great water sports and dining options on offer in Lower Matecumbe. Bringing your own boat? There’s a shared community ramp just outside the villa where you can launch your adventures into the sparkling sea.

Gorgeous Hotel in Lower Matecumbe: Caloosa Cove Resort

The guest reviews of this three-star hotel confirm you will receive a five-star service. If you’re visiting on a budget, Caloosa Cove Resort means you get to enjoy a small taste of luxury without breaking the bank. Rooms are spacious, and all of them come with a balcony. Hint: If you’re planning a romantic holiday, the ocean-view rooms give mesmerizing sunsets.

Dreamy Villa in Lower Matecumbe: The Island Dog Conch House

This one sleeps more guests, but it’s still pretty affordable. The interiors are bright and breezy, with calm vibes creating the perfect space for a summer getaway. It’s a little bit further away from the marina, but you can still reach it within a short drive. There is a shared community pool and boat ramp with other villas in the resort.

3. Plantation Key – Best Area in Islamorada for Families

The largest island in the region, Plantation Key is the perfect spot for families heading to Islamorada. In the south you will find Rain Barrel Village, a local creative commune that is a true haven for artsy types. For those traveling with kids, they even offer workshops to satisfy the entire family.

Windley Key is right next door and is home to a water park, local boutiques, and laid-back restaurants. This makes it another great option for families, and is a great place to visit even if you do stay on Plantation Key.

Top Things to Do in Plantation Key

1. Theater of the Sea is a popular water park giving you the chance to swim with dolphins, snorkel in the sea and check out the aquatic shows.
2. Island Grill is a great restaurant to take the kids to; their tuna nachos might sound a bit off the wall, but they’re super famous with the locals.
3. Old Road Gallery is a really unique boutique that offers local antiques and doubles as a local art gallery.
4. Toilet Seat Cut, a collection of toilet seats suspended above the sea, is certainly one of the most unique photo spots in the world.

Peaceful Family Home in Plantation Key: Waterfront Townhouse

Housed within a gated community, this secluded resort is a great spot for smaller families heading to Islamorada. You can also opt to rent out your own private boat slip for launching your yacht into the sunny waters. There’s a small balcony in the living room that offers gorgeous sunset views in the evenings. This townhouse is somewhat basic, but perfect for a peaceful staycation in the Florida Keys.

Charming House near Plantation Key: Anglers Reef

This is actually located in neighboring Windley Key, so you’ll be well connected to both Plantation Key and Upper Matecumbe. The surrounding state park is filled with gorgeous native plant life and local birds. Two kayaks are included with the property, with private slips into the ocean available within the resort. Angler’s Reef strikes the perfect balance between peaceful serenity and having plenty of things to do.

Friendly Resort in Plantation Key: Pelican Cove Resort & Marina

With most rooms sleeping up to five guests, this is a great choice for families sticking to a budget. Alongside the affordable room rates, you’ll benefit from a private stretch of beach and saltwater lagoon for bathing, so make sure you pack your sunscreen! A continental breakfast is provided every morning, helping save you even more money. This is our top pick in Islamorada on a budget.

Here’s what people usually ask us about the areas of Islamorada and where to stay.

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Islamorada is a gorgeous destination and by far the most relaxing place to stay in the Florida Keys. With sunset restaurants, cool theme parks, and dazzling beaches, you won’t be short of things to do. Plus, the crowds here are smaller, and the locals are known for their laid-back attitude. Islamorada is a great choice for a calm vacation in the United States – especially if you’re chasing that all-important winter sun.

If we had to pick a favorite area, it’s gotta be Upper Matecumbe Key! This island is right in the heart of Islamorada, giving you plenty of opportunities to explore everywhere else mentioned in this guide. It also offers some of the region’s best views, with a great balance between things to do and places to unwind.

That being said, the best place for you really depends on what you want to get out of your stay. You’ll need to bring a car, so why not take a little Florida road trip to make the most of the area? We hope this guide has helped you narrow down your options for your upcoming trip.

Did we miss anything? Let us know in the comments!