The Caribbean Resort Islamorada: A Tropical Paradise in the Florida Keys

If you’re wondering where to stay when visiting Islamorada, Florida, the Caribbean Resort Islamorada is one of the best places to choose!

In this post, this guide covers everything you need to know about staying at the Caribbean Resort in Islamorada, Florida. I cover the layout of the resort, the various amenities, and what you can expect from each house on property!

I’ve been to the Florida Keys over 10 times, and a majority of those times, I have stayed at the Caribbean Resort. Not only have I stayed here multiple times, I even got married here, so the Caribbean Resort Islamorada holds a special place in my heart!

So keep reading if you are considering a stay at the Caribbean Resort Islamorada!

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! 

Everything You Need to Know about Staying at the Caribbean Resort Islamorada

The Vibe

The Caribbean Resort Islamorada isn’t your average hotel. In fact, it’s not really a “hotel” at all! No long hallways, no luggage carts, no conference rooms.

The Caribbean Resort is a place to unplug, unwind, and relax in paradise. You’ll find no on-site bars or restaurants here either (but don’t worry, there’s plenty nearby!). With only 22 unique, Caribbean-style homes, the resort is extremely private and quiet.

Located right on the Atlantic Ocean, you’ll immediately feel at peace here, waking up to the ocean breeze and watching the sunrise from the dock.

The overall footprint of the Caribbean Resort Islamorada is quite small – you can walk from one end of the property to the other along the single path in less than five minutes. Yes, it’s that small!

The resort is tucked away in between lush foliage and is the perfect place to get away from all of your responsibilities! Check out the map below to see layout of the resort!

P.S. Planning a trip to the gorgeous Florida Keys? Don’t forget to check out my Ultimate Florida Keys Travel Guide for more tips on when to visit, how to get there, and must know info before your trip!

The Location

As I mentioned, the Caribbean Resort is located in the sports fishing capital of the world, Islamorada, Florida! Technically, the resort is located on Upper Matecumbe Key, one of the many islands in the “Upper Keys”, which stretches from Key Largo to Islamorada.

Islamorada is actually a town that spans a few different keys, where you’ll find some of the best fishing and diving in the world.

Less than 2 hours from Miami International Airport, Islamorada is perfectly located in the Keys.. You miss the Key Largo crowds here (many people travel from Miami to Key Largo on a day trip).

Plus you’re less than 2 hours away from the crazy Key West! Islamorada is truly the perfect slice of paradise in the Keys.

If you’re flying into Florida to visit Islamorada, I recommend looking into both Fort Lauderdale and Miami airports. From there, you’ll need to rent a car and make your way across the Overseas Highway (“The Stretch”, as the locals call it!) into the Keys.

P.S. You can read more about traveling into the Florida Keys in my Ultimate Florida Keys Travel Guide.

The Rooms

Like I mentioned, the Caribbean Resort Islamorada is home to a collection of gorgeous, Caribbean-style houses, each one beautifully decorated with local nautical décor, like coral and driftwood.

The houses vary in size and layout, so there are options for every budget and family! (Although I would still categorize this as a luxurious resort).

Almost all of the houses have wrap-around veranda porches, washers and dryers, and outdoor grills. They all have kitchens (some full kitchens, some with “kitchenettes”), which makes it very convenient if you’re staying for a long weekend or a week! 

Below I will provide a breakdown of the different houses to help you choose which is right for you!  You can also use the link below to check availability and book directly on TripAdvisor.com!

Hemingway, Canary Island & Princess Palm

2 Bedrooms | 2 Bathrooms | Sleeps 8

1 king bed, 2 full beds, & 1 pull out couch

These 3 sets of houses are pretty much identical in terms of room layout and size. Each house is split into two different sides, North and South, which are identical, flipped designs. Each side sleeps 8 total, with one master bedroom (king bed), an additional bedroom (two full beds), and a queen sleeper sofa in the living room. Canary Island and Princess Palm are on either end of the resort pool, and Hemingway is right across the gravel “road” (probably less 50 steps!) so you really can’t go wrong with any of these houses!

Malayan Palm North & East

The Malayan Palm is a unique house because it can actually be opened up via a locked interior door to make one big house, but each side is still rented out separately like the 3 above. Malayan Palm North is the bigger of the two sides, with two bedrooms, both with a queen bed, and one bathroom. Malayan Palm East is a bit smaller, with just one bedroom and one bathroom plus a pull out couch. And again, if you have a big party, you can rent out both sides and open the inside door to make it a 3 bedroom, 2 bathroom house, sleeping 10 total!

Jamaican Palm

3 Bedrooms | 2 Bathrooms | Sleeps 9

3 queen beds & 2 pull out couches (1 twin, 1 queen)

My favorite house on the property, the Jamaican Palm is unlike any other! It’s the only house on the property that has 3 separate bedrooms, each with queen beds. Plus there’s a mini bonus room off the master with a twin pull out couch and a pull out couch in the living room. So in total, it sleeps 9 people! All of the houses have kitchens or kitchenettes.. but the kitchen in the Jamaican Palm is absolutely to die for. Custom teal cabinets, a hidden cabinet fridge, and a double oven are just some of the highlights. Plus, the house is right across from the pool. There’s a reason it’s my favorite house!

Harbor House, Fish Tail Palm, and Bird of Paradise

All three of these houses are much smaller than the ones mentioned previously but are still gorgeous homes!

The Harbor House is moderately sized with two bedrooms, two bathrooms, and a pull-out couch. Perfect for a family of 4-6! It’s also closer to the dock and marina than the houses already mentioned but still only a stone’s throw away from the pool!

The Bird of Paradise and Fish Tail Palm houses are the smallest on the property, both one bedroom and one bath but still have pull out couches in the living room, so they sleep 4! Perfect for couples or small families.

Both houses are close to the marina and the dock, so you can wake up and walk right out onto the pier to watch the sunrise! The Bird of Paradise house is the property’s ADA accessible home and is reserved for guests with disabilities unless all other homes are full.

Royal Palm (North and South)

3 Bedrooms | 3 Bathrooms | Sleeps 8

1 King bed, 1 Queen Bed, 2 Twins, & 1 Pull-out couch

Alright, I have saved the most extravagant for last! The Royal Palm (also referred to as “The Big House”) is the biggest and most expensive house on the property! Like the larger houses, The Royal Palm is split in half and rented separately, with both sides identical to each other.

It’s the only 2-story house on the property and boy does it stand out! With one master bedroom, one guest bedroom, an upstairs loft, plus a pull-out couch, it sleeps 8 total, similar to the other split houses on the property.

However, this house is significantly more expensive than the other houses, as it’s much larger and has the best views, with an upstairs wrap-around balcony that overlooks the dock, the tiki hut, and the gorgeous Atlantic Ocean. I mean look at this view!

I was lucky enough to stay here for my wedding, but I don’t think I’ll ever splurge on this house again. The Jamaican Palm offers more beds and is over $500 cheaper per night! But if it fits your budget, you won’t regret staying in the Royal Palm!

5 Little Palms and North & South

The resort also has long-term rental houses called the Little Palms. Although these homes are outside the main gates of the property, they all have full access to the main resort amenities and are still walking distance away from everything.

However, these homes can only be rented either weekly or monthly, so keep that in mind if you are planning a shorter trip!

Resort Amenities

The Pool

One of the best parts of this property is the incredible zero-entry pool and its surrounding landscape. And don’t worry, ALL of the houses are just walking distance from it.

Although there is only one pool on the property, it rarely feels crowded, as most people spend their days out on the water. And even if there are other people there, it’s a very large pool with plenty of room to spread out.

Plus, with only 22 homes on the property, there will still be significantly less people than at a typical resort pool. It is truly one of the most gorgeous pools I’ve ever been in!

There’s also a large jacuzzi that is fairly new and is a total game changer when it’s a little chilly out (which of course is not often – it’s the Keys!)

But if you’re a jacuzzi person, you will love this thing! It sits right in front of the Canary Island house and is the perfect place to unwind at the end of the night.

The Marina

If you’re visiting the Keys, I hope you are planning to get out on the water! If you’re not… think again! But seriously, the Keys, and Islamorada specifically, are known for their world-class sportfishing, diving, snorkeling, and marine life!

So even if it’s just a morning paddleboard, you need to experience the beauty of the Florida Keys water.

The Caribbean Resort Islamorada makes it easy to do just that, with its boat harbor and long, private dock that leads you out into a deep-water channel. You can borrow fishing poles from the resort free of charge and test your luck at the end of the dock!

I also highly recommend taking a stroll down the dock around sunrise or sunset, I guarantee you’ll see some incredible wildlife (probably a shark or two!)

The resort has one boat that they rent out with pretty good rates, so make sure to inquire early if you’re interested!  You can also rent a boat from nearby marinas and or bring your own, as long as it’s an outboard motor and less than 39 feet!

The resort charges $2.50 per foot per night, which includes access to the boat ramp, fish cleaning station, ice, electric and more.

In the middle of the marina, you’ll find a massive tiki hut with comfy lounge chairs and couches, the perfect place to relax after a day on the water. And don’t forget to keep an eye out in the harbor for a manatee or two!

Activity Rentals

If you don’t have a boat, don’t worry! There’s still plenty of ways to get out on the water. The resort has kayaks and paddleboards that are free of charge to resort guests. They don’t require reserving in advance either.

Just head over to the tiki hut in front of Bird of Paradise (shown below) and fill out a waiver to secure your rental! You are responsible for launching and returning it, but it’s very easy from the boat launch! If water activities aren’t your thing, the resort also has free bicycles to take around.

Nearby Attractions

The Caribbean Resort is located smack dab in the middle of Islamorada, so there are tons of places to explore around the resort! Below I’ll go over my favorites in case you need some recommendations. They’re also linked in the map below!

Restaurants

Make sure to check out my full guide on the Best Restaurants in Islamorada to help you decide where to eat while staying at the Caribbean Resort! Below is a quick summary of my favorites.

Islamorada Shrimp Shack – Walking distance from resort, featured on Diners, Drive-Ins & Dives!

Lorelei Restaurant – Walking distance (just across the street), gorgeous place to watch the sunset!

Islamorada Brewery & Distillery – Less than a mile away, local beer, liquor and food trucks!

Florida Keys Brewing – Another brewery with a beer garden, just down the road!

Robbie’s Marina – Tourist spot to feed the tarpon plus yummy food and drinks!

Morada Bay – Bayside restaurant on gorgeous beach, great place to watch the sunset!

Square Grouper – Waterfront restaurant with delicious seafood and live music!

Other Places to Check Out

Besides restaurants, there are a ton of other cool places in Islamorada to check out. If you’re looking for a beach (which are quite rare in the Keys to most people’s surprise), you can check out Founder’s Park, just a few miles up the road from the Caribbean Resort.

If you’re looking to do some shopping, head over the Rain Barrel Village for some local paintings and souvenirs. And if you are looking for an adventure, you can also head over to Robbie’s Marina (mentioned above), rent some kayaks, and head over to Indian Key State Park! And my favorite place in Islamorada is Alligator Reef Lighthouse, which you will need to rent a boat or hop on a snorkel tour to visit!

If you’re looking for more ideas on what to do, you can check out my Key Largo to Key West Road Trip Itinerary to help plan your trip!

Final Thoughts

I hope I’ve convinced you that the Caribbean Resort Islamorada needs to be on your bucket list! With its gorgeous homes, lush landscapes, and beach-entry pool, it’s one of the most beautiful resorts in the Florida Keys and transports you into a tropical paradise.

There’s enough to do in the area to fill a week, but a long weekend will do if that’s all you can spare. Don’t miss this incredible resort if you are visiting the Florida Keys!

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