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!
The Russell Estate | Secluded Luxury in 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.
Anglers Reef | Mesmerising Views in 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.
Caloosa Cove Resort | Captivating Resort in 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.
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 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
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 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.
The Russell Estate | Luxurious Retreat in Upper Matecumbe
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.
Houseboat | Peaceful Hideaway in Upper Matecumbe
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.
Cheeca Lodge & Spa | Luxury Hotel in Upper Matecumbe
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:
- We can’t get enough of the sunset views from the restaurants here – Islamorada Fish Company offers a great menu and sunset shark feedings.
- The Keys History & Discover Centre offers fantastic exhibits detailing the history and culture of this beautiful region.
- Unwind among the mangroves at Library Beach Park – there are also some barbecue facilities available to use free of charge.
- 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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View on Osprey View on REI2. 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.
Islamorada Escape | Peaceful Beach House in Lower Matecumbe
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.
Caloosa Cove Resort | Gorgeous Hotel in Lower Matecumbe
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.
The Island Dog Conch House | Dreamy Villa in Lower Matecumbe
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.
Things to See and Do in Lower Matecumbe:
- Habanos Oceanfront Dining has casual vibes, gorgeous views, and a simply unmissable Cuban food and drinks menu.
- 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.
- 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
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.
Waterfront Townhouse | Peaceful Family Home in Plantation Key
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.
Anglers Reef | Charming House near Plantation Key
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.
Pelican Cove Resort & Marina | Friendly Resort in Plantation Key
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:
- 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.
- 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.
- Old Road Gallery is a really unique boutique that offers local antiques and doubles as a local art gallery.
- 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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Hide Yo’ Money!FAQs About Where to Stay in Islamorada
Here’s what people usually ask us about the areas of Islamorada and where to stay.
What To Pack For Islamorada
Pants, socks, underwear, soap?! Take it from me, packing for a hostel stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.
Ear Plugs
Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.
Hanging Laundry Bag
Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.
Sea To Summit Micro Towel
Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.
Monopoly Deal
Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.
Grayl Geopress Water Bottle
Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!
Check out my definitive Hotel Packing list for even more top packing tips!
Don’t Forget Travel Insurance for Islamorada
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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!
- Check out our ultimate guide backpacking around USA.
- Figured out where you wanna stay? Now it’s time to pick the perfect hostel in USA.
- Or… maybe you want to check out some Airbnbs in USA instead.
- Next up you’re gonna need to know all the best places to visit in USA to plan your trip.
- Save yourself hassle and money and get an international sim card for USA.
- Swing by our super epic backpacking packing list to prep for your trip.
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!
