The 7 BEST Hotels in Islamorada, Florida

If you are planning to visit Islamorada in the Florida Keys, you might be wondering where the best place to stay on your vacation is!

There’s no doubt Islamorada is full of incredible places to choose from. From affordable beachside cottages to five-star resorts, there is something for everyone in this slice of paradise!

As a kid, I grew up visiting Islamorada every year for the 4th of July! Now as an adult, we make a point to return at least once a year, so I’ve stayed at plenty of different spots in Islamorada.

In this post, I’ve curated a list of my top 7 favorite hotels in Islamorada to help you narrow down your options.

I’ve also included other helpful information on each hotel, like average prices, amenities, and more! Whether you’re visiting Islamorada to go sports fishing, scuba diving, or just relax by the pool, there is a resort out there for you, and I hope this list gives you a great starting point!

All About Islamorada, Florida

Before we get into the list, here are some quick facts about Islamorada, with some helpful links to help plan your trip! 

Islamorada is a major town/village in the Florida Keys, and it actually encompasses six different keys (Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key). 

If you are driving from Miami, Islamorada is the second major village you will hit, right after Key Largo! 

Islamorada is home to some incredible activities, restaurants, and of course, hotels! In fact, Islamorada is my personal favorite place to stay in the Florida Keys thanks to everything it has to offer.

Overall, staying in Islamorada during your Florida Keys road trip is a must do! Now, let’s take a look at the best hotels in Islamorada to help you choose.

The BEST Hotels in Islamorada, Florida: Where to Stay and Why

As mentioned above, Islamorada is actually made up of six different islands, but they all blend together when you are in the Keys! Seriously, crossing over bridges happens almost every time you go for a drive!

Although there’s several islands, Islamorada still has a small town feel, as it only stretches 20 miles from one end to the other.

The below map shows the most popular places to stay within that range, but I will also break down my favorites below! You can’t go wrong with any.

One important thing to know before visiting the Keys is that most restaurants and hotels are located not only by their address, but by their mile marker. Islamorada lies approximately between Mile Mark 91 and Mile Marker 71.

Below are a few popular Islamorada attractions and their corresponding mile markers:

• 86.8 = Betsy the Lobster
  84.3 = Islamorada Visitor’s Center
• 83.0 = History of Diving Museum
• 82.0 = Lorelei Restaurant & Cabana Bar
• 77.0 = Robbie’s of Islamorada

Most of the hotels I’m recommending below are around Mile Marker 82!

The Caribbean Resort

Address: 17 Carroll St, Islamorada, FL 33036
Mile Marker: 82
Average Price: $650/night
Best For: Large Groups, Those Looking for Privacy

I may be a little biased, but the Caribbean Resort is one of my favorite hotels in the world.

Why?! Because I got married here!!! And grew up coming here as a kid.

Aside from that little fun fact, the Caribbean Resort really is one of the most incredible resorts in the entire Florida Keys (not just Islamorada).

The resort is made up of 22 luxury homes that you can rent out individually (each sleep between 4-10 people). The property is quite small compared to other resorts in the Keys – you can walk from one end to the other in less than 5 minutes.

For this reason, it has a very secluded feel, which is why I love it! Most days, you’ll feel like you have the entire place to yourself.

There are no bars or restaurants on site, but each house has a full kitchen where you can cook your own meals.

At the center of the resort lies the gorgeous, zero-entry pool, surrounded by two hot tubs, lush foliage, cabanas, and beach chairs.

There’s also an on-site marina, huge tiki hut, and long fishing dock where you can fish, look for wildlife, and watch the sunrise! And make sure to take advantage of the free kayaks and bikes.

In short, if you can splurge and have 4+ people, the Caribbean Resort is my number one recommendation for the best hotel in Islamorada.

You can read my full review of the Caribbean Resort here for even more information on this incredible property!

Cheeca Lodge & Spa

Address: 81801 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 82
Average Price: $300/night
Best For: Couples, Golfers

A close second for best Islamorada hotel after the Caribbean Resort goes to the Cheeca Lodge & Spa. Located just down the road from the Caribbean Resort, Cheeca Lodge has a gorgeous property and stellar rooms.

It’s also one of the only resorts in the entire Florida Keys that has a golf course on property.

There’s also a wonderful spa, and you can even book a room with a hot tub on your balcony! So glamorous!

Also, right off shore from Cheeca Lodge is the gorgeous Cheeca Rocks, one of the best snorkeling spots in Islamorada.

Cheeca Lodge definitely has more of a “hotel” feel than Caribbean Resort. By that I mean, there are a couple on-site restaurants, a coffee bar (and a real bar), and other amenities that Caribbean just doesn’t have.

The rooms are also standard hotel rooms (not large houses).

Cheeca Lodge is a great choice for your trip to Islamorada, especially if you are traveling as a couple! I am already looking forward to when I get to stay here again!

Psst: Planning a trip to the Florida Keys? Don’t forget to check out my Ultimate Florida Keys Travel Guide!

Three Waters Resort & Marina

Address: 84001 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 82
Average Price: $600/night
Best For: Couples, Small Groups, Families

Previously the Postcard Inn Beach Resort, Three Waters Resort and Marina is a great place to stay in Islamorada if it is your first time visiting!

This resort has recently been completely renovated and rebranded to a more luxury-style property and is now a “Tribute Portfolio” resort from Marriott. With this rebrand came an increase in the standard room rate.

Luckily, they didn’t get rid of my favorite part of the resort – the famous Tiki Bar! Formally known as the Holiday Isle Tiki Bar (before they rebranded), this Tiki Bar has been operating since 1969.

Fun Fact: the renowned Rum Runner cocktail was invented here!!! Even if you choose not to stay at Three Water, the Tiki Bar is worth a stop on your trip.

Aside from the Tiki Bar, Three Waters Resort has so much to offer. On site, there are three swimming pools, as well as three walk-in beaches, which is quite rare for the Keys!

They also have complimentary kayaks, paddle boards, and bikes, plus an arcade. There’s also plenty of on-site dining, including a pizza shop, ocean-front and poolside restaurants, and a Starbucks!

Overall, this resort has everything you need to have an incredible stay in the Florida Keys without even needing to leave the property.

The Islander Resort

Address: 82100 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 82
Average Price: $400/night ($1000 for suites)
Best For: Families, Dog Owners, Adventure Lovers

The Islander Resort, located right next to the Caribbean Resort, is another great choice for your stay in Islamorada. It is very similar to Three Waters Resort, with standard hotel rooms, multiple swimming pools, restaurants, bars, etc.

However, Islander also has more luxurious “bungalow” style rooms, called oceanside signature suites, if you want to splurge. These rooms have kitchens, living rooms, etc., similar to the houses at Caribbean Resort.

Plus, Islander also has a more family-friendly vibe than the other hotels I’ve mentioned so far. There’s a splash pad on property, fun beachside games, and equipment like kayaks, paddle boards, etc.

They are also pet friendly and have a little dog park on property!

In addition, Islander also partners with Clearly Unique Watersports to provide great deals on water sports rentals, snorkel tours, boat charters, sandbar swims, sunset cruises, and more!

All of these reasons make Islander one of the best Islamorada hotels in my opinion!

Amara Cay Resort

Address: 80001 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 80
Average Price: $350/night
Best For: Couples, Eco lovers, Families with older children

Another great choice for your stay in Islamorada is the Amara Cay Resort. Owned by the same resort collection as Three Waters, Amara Cay gives off “laidback luxury” vibes and feels like a boutique hotel.

This hotel has a marina on site and also partners with Wild Dolphin Tours and Islamorada Spearfishing Adventures right off their dock, so it’s extremely easy to experience the ocean adventures of Islamorada while staying here.

My favorite part of the resort, however, is their focus on sustainability. They are recognized by the Florida Green Lodging program, which means they make a commitment to conserve and protect Florida’s natural resources.

The resort supports the local community and foundations like the Islamorada Coral Conservation and Restoration. In addition, they have several initiatives across the resort, like no plastic straws, uilizing LED lighting, and planting local flowers and trees!

La Jolla Resort

Address: 82216 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 82
Average Price: $200/night
Best For: Budget travelers, those looking for a local vibe

If you’re looking to embrace the essence of the Florida Keys and “old Florida”, look no further than La Jolla Resort. This hotel definitely has less frills than the others mentioned in this post, but that doesn’t mean it’s not worth staying at

La Jolla is a small, quiet resort with 6 colorful, retro-inspired buildings. They’re all been recently renovated and each have their unique feel. The resort also has a small outdoor pool, plus free kayaks, paddle boards, and bicycle rentals you can use during your stay.

One of the best parts, however, is that this resorts sits on the bayside, which means you get a front row seat to the stunning Islamorada sunsets. Grab your loved one and a glass of wine and enjoy nature’s show every night of your stay!

La Siesta Resort & Villas

Address: 80241 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 80.2
Average Price: $300/night
Best For: Groups & Families

Last but not least, La Siesta Resort & Villas is another hidden gem and one of the best hotels in Islamorada! Owned by the same company as Amara Cay and Three Waters, La Siesta has something for everyone!

On property, there are colorful beachfront casitas, coastal villas, ocean suites, and garden suites. This is a great choice if you have a larger family and want to stay together in one room, since a lot of their suites sleep 6-8 people.

The property also has an on-site marina, a pool, and a bar! They also have kayaks and bicycles you can use during your stay.

This hotel is one of the best rated in Islamorada and is great for families, couples, and groups!

Other Things to Know about Visiting Islamorada

There is truly no shortage of things to do in Islamorada!

Most people come to Islamorada to take advantage of the unbelievable underwater landscapes. Thanks to the Florida Keys National Marine Sanctuary, Islamorada has some of the best snorkeling in the entire world.

In fact, my favorite place in all of the Florida Keys is Alligator Reef Lighthouse in Islamorada, Florida. The amount of fish and other wildlife underneath the lighthouse is jaw-dropping.

Another option is to head a bit north and go snorkeling in Key Largo at the famous John Pennekamp Coral Reef State Park, home to the underwater Christ statue!

If you are scuba-certified, there are plenty of awesome dive spots to keep you busy, thanks to the Florida Keys Wreck Trek!

Islamorada is also the Sports Fishing Capital of the World, so it’s a great place to try your luck at catching some big game fish!

There’s also plenty of relaxing to be had in Islamorada, whether that’s at the famous Islamorada Sandbar or at your hotel’s pool bar.

I hope this guide was helpful in determining where you should stay on your trip to Islamorada. Like I mentioned, there is no shortage of incredible options, but these are my top 7 choices for the best hotels in Islamorada.

Next, be sure to check out my guide to the BEST Islamorada Restaurants You MUST Try to continue planning your Florida Keys adventure!

Don’t forget to pin this post for future planning!