Right in the heart of the Florida Keys, Islamorada is the perfect base for exploring the stunning region on the southern tip of the United States. With warm weather all year round, this is a great spot for some last-minute winter sun. Islamorada is known for its golden beaches, peaceful shores, and laid-back restaurants offering sunset views. Scratch beneath the surface, you’ll also find some quirky local attractions waiting to be discovered.

While connected by a bridge, Islamorada is actually a collection of islands. This means it’s important to plan your stay well in advance. Each island offers something a little different, so doing a little bit of research will help you better plan your stay.

Which is where we come in! We’ve figured out the three best places to stay in Islamorada by combining our own experience with hints and tips from locals and travel experts. Whether you want to kick back and relax, soak up the easy-going nightlife, or simply enjoy an affordable staycation, we’ve got you covered.

So let’s dive right in!

Where to Stay in Islamorada

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    Secluded Luxury in Islamorada – The Russell Estate

    The Russell Estate Islamorada

    Escape for a while at this gorgeous holiday home right on the oceanfront! Alongside charming sunset views, the interiors are modern and spacious – letting in lots of natural light. What really makes this property stand out, however, is the outdoor area. It comes with a large private pool, secluded dock, and a small section of beach. This is one of the best Airbnbs in Florida for those that want to get away from it all.

    Mesmerising Views in Islamorada – Anglers Reef

    Anglers Reef 1, Islamorada

    Relive Islamorada’s heyday in this gorgeous villa in the heart of the region. It’s nestled among the mangroves and surrounded by a state park, creating a secluded and exclusive vibe. It’s part of a larger resort, so you’ll also get to enjoy communal facilities like a heated pool and boat slips. Sleeping up to six people, this is a great pick for larger families and groups heading to the area.

    Captivating Resort in Islamorada – Caloosa Cove Resort

    Caloosa Cove Resort, Islamorada

    Sometimes you just want the convenience of a hotel, and Caloosa Cove Resort is both affordable and well serviced. It has fabulous guest reviews thanks to the above-and-beyond guest service and gorgeous sea views. The pool and terrace are well placed for watching the sunset, making this a great choice for a romantic getaway. Their private beach also means you can avoid the big crowds at the public beaches.

    Islamorada Neighborhood Guide – Places to Stay in Islamorada

    Upper Matecumbe Key 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.

    Lower Matecumbe Islamorada

    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.

    Plantation Key Islamorada

    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.

    Islamorada’s 3 Best Places to Stay

    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 Islamorada
    Upper Matecumbe Key is perfect for adventure lovers.

    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.

    Luxurious Retreat in Upper Matecumbe – The Russell Estate

    The Russell Estate Islamorada 1

    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

    Houseboat Islamorada

    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

    Cheeca Lodge and Spa Islamorada

    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.

    Things to See and Do in Upper Matecumbe:

    Things to See and Do in Upper Matecumbe
    There’s plenty of activities to keep everyone entertained.
    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.
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    2. Lower Matecumbe Key – Where to Stay in Islamorada for Couples

    Lower Matecumbe Islamorada
    A perfect seaside retreat.

    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.

    Peaceful Beach House in Lower Matecumbe – Islamorada Escape

    Islamorada Escape Islamorada

    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

    Caloosa Cove Resort Islamorada 2

    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

    The Island Dog Conch House Islamorada

    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.

    The Island Dog Conch House is one of our favourites in Islamorada but they’re not taking guests right now. We’re not sure if they’re closed for good but we hope they’ll come back soon.

    Things to See and Do in Lower Matecumbe:

    Things to See and Do in Lower Matecumbe Key Islamorada
    Islamorada is a top spot for ocean-lovers.
    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.

    3. Plantation Key – Best Area in Islamorada for Families

    Plantation Key Islamorada
    Plantation Key is our top choice for visiting 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.

    Peaceful Family Home in Plantation Key – Waterfront Townhouse

    Waterfront Townhouse Islamorada

    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

    Anglers Reef Islamorada

    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

    Pelican Cove Resort and Marina Islamorada

    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.

    Things to See and Do in Plantation Key:

    Things to See and Do in Plantation Key
    The kids won’t get bored here!
    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.
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    Final Thoughts on Where To Stay in Islamorada

    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!

    And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!