The 7 BEST Hotels in Islamorada, Florida

If you are planning to visit Islamorada, Florida, 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!

In this post, I provide a list and overview of the 7 best hotels in Islamorada, including some of my personal favorites!

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!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you!

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! 

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

Now that you have a good feel for Islamorada, let’s get into the list of the best hotels and resorts!! Most of these hotels 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 my favorite hotel in the Florida Keys!!

Why?!

Because I got married here!!! Please enjoy some photos that showcase how gorgeous this resort is..

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. On the property, there are no restaurants or bars, so it really doesn’t feel like a “hotel”.

It’s more of a secluded resort, with a private dock and marina, plus free kayaks and bikes to use.

You can read my full review of the resort here for even more information. In short, if you can splurge and have 4+ people, this is my number one recommendation for the best hotel in Islamorada.

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.

Photo Credit: Cheeca Lodge from Booking.com

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).

This is a great choice for your trip to Islamorada – 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!

Postcard Inn Beach Resort

Address: 84001 Overseas Hwy, Islamorada, FL 33036
Mile Marker: 82
Average Price: $250/night
Best For: Couples, Small Groups, Families

Recently renovated, the Postcard Inn Beach Resort is a great place to stay in Islamorada if it is your first time visiting! Even if it’s not your first time, I still think Postcard is one of the best hotels in Islamorada, and it won’t break the bank!

One of my favorite parts about Postcard Inn is that it’s home to the famous Tiki Bar! Formally known as the Holiday Isle Tiki Bar (before they rebranded to Postcard Inn), 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 Postcard Inn, the Tiki Bar is worth a stop on your trip.

Photo Credit: Postcard Inn from Booking.com

Aside from the Tiki Bar, Postcard Inn has so much to offer. On site, there are two swimming pools, a private beach and ocean lagoon, a marina, an on-site raw bar, fireplaces, bicycles, and more!

This resort has everything you need to have an incredible stay in the Florida Keys. Plus, it’s very reasonably priced, and the rooms are all recently renovated!

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 Postcard Inn, 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.

Photo Credit: Islander Resort from Booking.com

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 Postcard Inn, 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.

Photo Credit: Amara Cay Resort from Booking.com

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!

Photo Credit: La Jolla Resort from Booking.com

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: $500/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 Postcard Inn, La Siesta has something for everyone!

On property, there are colorful beachfront casitas (shown in the photo below), coastal villas, ocean suites, and garden suites.

Photo Credit: La Siesta Resort & Villas from Booking.com

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! Of course, the number one thing to do is to get out on the water!

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

Not certified? No worries, there are plenty of shallower snorkel spots in Islamorada, like Alligator Reef, Cheeca Rocks, and Hens and Chickens. Or, you can head a bit north and go snorkeling in Key Largo at the famous John Pennekamp Coral Reef State Park.

If you are not an avid swimmer, there’s still plenty to do on the water in Islamorada. Islamorada is known as the sports fishing capital of the world, which means you can catch big game like marlin and wahoo here!

Or, book a trip out to the famous Islamorada Sandbar, where the water is clear, shallow, and perfect for lounging!

Also, don’t forget to check out my guide on the BEST restaurants in Islamorada, for a full list of where to eat when visiting this incredible town!

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. Enjoy paradise and the ocean views!!

Make sure to check out my other Florida Keys blog posts to help plan your trip!
Ultimate Florida Keys Travel Guide
Best Time to Visit the Florida Keys
Best Hotels in Key Largo, Florida
Upper Keys Travel Guide