best resorts in islamorada florida keys

Best Places to Stay: Islamorada, Florida Keys

Choosing where to stay when planning a vacation can be tough because it’s natural to want everything to be perfect. With so many accommodations in Islamorada, choosing the right place to stay can be overwhelming. Lucky for you, we have stayed at a lot of the hotels here, so we know a bit about the best places to stay in Islamorada.

We haven’t stayed at every hotel in Islamorada, but we have stayed at most of the main ones. Every single accommodation in this article is a place we have personally stayed. I would recommend any of these hotels in Islamorada except perhaps the very last one mentioned in the article. We enjoy each of these resorts for different reasons. I’ll start with categories you may be looking for (such as best best resorts in Islamorada for families) then I’ll go into detail on each accommodation.

Finally, I do use the term hotel and resort interchangeably throughout the article. In Islamorada, they are primarily considered resorts which means they may have things such as food, water excursions, shuttles, and more. What each resort in Islamorada offers is a bit different than the next but each place does have more than your standard hotel. This also means that there is a daily resort fee, which varies in price from place to place.

What are the Best Islamorada Hotels on the Beach?

“What are the best Islamorada hotels on the beach?” I get this question a lot. And it’s a fair question. When you’re going to be spending your vacation on a tropical island, it’s only natural to assume want to spend time relaxing on the beach. I want to provide a quick disclaimer about the beaches in Islamorada (which is true throughout the Florida Keys, actually).

Beach conditions aren’t ideal in the Florida Keys if you’re expecting long stretches of sugar white sand. The Florida Keys are coral islands, making the beaches “rocky.” Additionally, seagrass is quite common. As you know, it gets pretty hot in the Florida Keys. So what happens when that seagrass washes up and sits in the sun? You guessed it, it can smell. 

Believe it or not, despite being a beautiful chain of islands, the Florida Keys actually don’t tend to have great beaches. 

I personally still love beaches in the Florida Keys. These things truly don’t bother me too much but I do hear that unknowing visitors can be disappointed. You may also see this disappointment reflected in the reviews of resorts you may be looking at. I want you to have realistic expectations. I also want you to know that resorts without pristine sandy beaches aren’t at fault, it’s just the nature of the area (literally).

Despite the beaches being a bit different that what you might have been expecting, they’re still breathtaking. The water in the Islamorada (and the rest of the Florida Keys) is unlike anywhere else. So you may still enjoy laying out on the beach or relaxing with the view from your hotel room. Each of the accommodations in this post are waterfront Islamorada hotels.

waterfront resort islamorada

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Best Islamorada Hotels for Couples

Casa Morada & Cheeca Lodge

Best Resorts in Islamorada for Families

Islander Resort, Amara Cay, and Pelican Cove/Postcard Inn

Best Islamorada Hotels for a Girl’s Weekend

Islander Resort & Amara Cay

Best Islamorada Hotel on a Budget

Fisher Inn.

Keep in mind that the Islamorada and budget don’t really go together all that well. The Florida Keys are not a cheap place to visit, and Islamorada is no exception. However, when researching the Florida Keys, the Fisher Inn is consistently cheaper than other Islamorada hotels.

places to stay islamorada

Cheeca Lodge and Spa

Cheeca Lodge and Spa is probably one of the most recommended resorts in Islamorada. I believe Cheeca Lodge lives up to the hype. This is one of those resorts that I find myself not wanting to leave. There is plenty to do in the area, but if you like taking it easy and hanging back at your resort, this is a good place to do it. They have multiple fine dining restaurants on site including steaks and seafood at Atlantic’s Edge, pizza and pasta at Mia Cucina, sushi at Nikai, and two tiki bars. The sushi at Nikai is the best sushi I have ever had. The room service was delicious, too, especially their dessert and brussels sprouts.

Located on 27 acres, the hotel has adult and family pools, a golf course, and a spa. The rooms are spacious and have very relaxing balconies. Some of the rooms even have a soaking tub on the balcony with water views. I would really like to stay in one of these rooms, but we stayed at the height of travel season, so we couldn’t justify the splurge. We plan to come back when it’s a little more affordable. Finally, like many resorts in the Florida Keys, you can enjoy plenty of water activities such as snorkeling, kayaking, biking, and boating. Some of these activities are and extra charge, but all conveniently located on site.

Cheeca Lodge is also walking distance to Cafe Moka, my favorite place to grab coffee in Islamorada, and the Florida Keys Brewing Company, one of our must visits in Islamorada each time we are in town. They also have a shuttle that will bring you anywhere in a one mile radius.

Why we love Cheeca Lodge and Spa

  • Great location. Being able to walk to the brewery is a huge plus to us.
  • Most hotels in Islamorada don’t have shuttles and a one mile radius is huge on such a small island.
  • The restaurants are really, really good.
  • The grounds are absolutely stunning.
  • Our room was large, bright, and airy. Plus, even though we were not in any sort of waterfront room, we had peek-a-boo views of the water.

Cons of Cheeca Lodge

  • It’s expensive
best resorts islamorada

Casa Morada

Casa Morada is a boutique hotel. It is very quaint with only 16 rooms. We loved how quiet and romantic it was and felt so refreshed after our stay. It is also worth noting that no kids under the age of 16 are allowed.

In complete disclosure we splurged for a room with a water view here. Not all of the rooms have water views and some are located a decent walk from the water. However, those rooms are located in a tranquil garden area and are still beautiful; it just depends what you prefer. Casa Morada is also the only hotel on this list of places to stay in Islamorada that is on the Gulf side. I personally prefer the Atlantic side most of the time, but that’s totally a personal preference and the views here are still beautiful.

The downsides of Casa Morada are things that are not necessarily important to me but may be to you. First, their pool isn’t as extravagant as the pools at many other Islamorada hotels. The pool is also located on its own little “island.” Because there is a seawall, you can’t dip your toes in the Gulf. Again, that may or may not be important since many people find the beaches in the Keys to be too rocky anyways but here you don’t have the option at all.

We loved the location because we could bike to all of our favorite places in Islamorada. Bikes are included with your resort fee, they also have kayaks and stand up paddle boards. It’s also close to Loralei’s which is a bar and restaurant on the water famous for live music and sunset views.

Why we love Casa Morada

  • It’s very, very quiet. Sometimes we prefer to be where there is a lot of hustle and bustle, but Casa Morada forces you to really unwind and forget about the real world.
  • One of the most romantic places we have stayed.
  • Every room is different.
  • Perfect location made it easy to bike to some of our favorite spots like Loralei’s, Cafe Moka (for coffee), and the breweries

Cons of Casa Morada

  • We fond it a “pro” that kids under the age of 16 aren’t allowed, but if you have young kids in your group you won’t be able to stay here.
  • We prefer the Atlantic side
  • Some of the rooms are located pretty far from the water. This is important to me, but may not be to you and the rooms that aren’t on the water have stunning garden views.
Casa Morada boutique hotel in islamorada florida keys

Pelican Cove and Postcard Inn 

These are two separate resorts located next door to each other. Pelican Cove and Postcard Inn are sister resorts (part of the Islamorada Resort Collection) so if you stay at one, you get access to the other for no additional cost. Amara Cay and La Siesta are also included in the Islamorada Resort Collection but aren’t walkable from Pelican Cove and Postcard Inn (though they do have a shuttle that will take you there). We have not been to La Siesta yet, but the other 3 resorts have everything you could want. Unless you really love checking out different resorts or are staying for a longer period of time and really wanting a change of scenery, you probably don’t need to worry about that too much.

Pelican Cove is smaller but still has plenty of activities and everything you need. Postcard Inn is a bit bigger and while the amenities are similar, there are slightly more at Postcard Inn. We personally like staying at Pelican Cove because it’s quieter, then walking to Postcard Inn to use their amenities. We also find Pelican Cove to be cheaper when we compare the two properties. At Pelican Cove, every room comes with a balcony and view of the water. Some rooms will have a more obstructed view than others, though, so you may get just a peek-a-boo view. The resorts are walking distance to a marina so if you want to take a boat or fishing charter, you don’t have to go very far. Or if you want to bring your own boat, you can pay to dock it at the marina.

For food, Postcard Inn has Ciao Hound (Italian), a tiki bar (home of the original rum runner), Raw Bar (seafood and other island favorites), Kokomo Bar (a pool bar inspired by the Beach Boys), and a Starbucks. Plus, a little insiders tip – Postcard Inn has free snow cones and if you are 21+ you can add also add a shot for free.

Why we love Pelican Cove

  • Quiet, peaceful, and relaxing with a short walk to every amenity you could want
  • Without leaving, you have access to a pool and hot tub, plus kayaking and SUP boards
  • Rooms are updated and cozy
  • Continental breakfast (nothing too crazy, but it’s always a nice option)

Cons of Pelican Cove

  • While many find their location to be just fine, we prefer to be just a little further south.
  • Each room technically has a water view, though some views are much better than others 
pelican cove islamorada florida keys

Chesapeake Beach Resort

They were doing construction at the Chesapeake Beach Resort when we stayed so only about half of the resort was open at the time. We stayed in one of the newly renovated oceanfront rooms and loved it. The views alone made me never want to leave. Of course, there is a pool and they also have a hot tub, which we really enjoyed as we were there in the fall. Kayaks, paddle boards, and fishing rods are not included in the price of your stay but are able to be rented onsite.

For food, they are walking distance to Wahoos Bar and Grill, Whale Harbor Seafood Buffet, and the Rooftop SandBar (connected to Whale Harbor Seafood Buffet). There is also a marina next to Whale Harbor, so if you want to charter a boat, you’re in a good location to do so. Chesapeake Beach Resort is also pet friendly. I have seen reviews that others found the walls to be quite thin. We had people on both sides of us when we stayed and didn’t hear them. I think that’s a gamble based on who your neighbors are, which could be said for most resorts in Islamorada (or anywhere, for that matter). We found that the balconies aren’t quite as private as some of the other resorts, but again this could be nonissue depending on how much time you use on your balcony an whether your neighbors are balcony people.

What we love about Chesapeake Beach Resort

  • Walking distance to Wahoo’s, a bar and restaurant right on the water
  • Wahoo’s is also in a marina with boats for pretty much any type of charter you could want.
  • If you get a water view, you’ll never want to leave your balcony. You’ll also have a perfect view of the Islamorada sandbar. It’s so fun to watch the boats coming and going all day.
  • Recently renovated

Cons of the Chesapeake Beach Resort

  • We didn’t experience any noise from our neighbors, but many reviews indicate very thin walls. I think this can vary wildly based on who is next door to you, though and that’s kind of a gamble in any hotel.
  • Balconies are not as private as other resorts in Islamorada, but if you don’t spend much time on your balcony or your neighbor doesn’t spend much time on theirs, then this is not an issue.
  • Not sure if it was because they were doing construction when we were there, but there wasn’t enough parking and when we tried leaving one morning, we were blocked in because someone parked behind us.
chesapeake hotel islamorada florida

Amara Cay

Amara Cay had a lot of amenities to really remind you that you are on vacation. When we stayed, they had games and live music, but their activities are always changing so you never know what you might find. Of any resort in Islamorada, Amara Cay had the most activities. They have a shuttle within a 4-mile radius plus complimentary use of bikes, kayaks, paddle boards, and lawn games. They also have an on-site restaurant, Reelcatch, which serves a little bit of everything from burgers to seafood.

The pool at Amara Cay is beautiful and they also have a tiki bar where you can order cocktails or food. They had someone playing the steel drums when we visited which added a nice vibe. I like Amara Cay’s location, which was walking distance to Lazy Days, a restaurant right on the water. It is waterfront, but note that to take a dip, you’ll enter the water via ladder, kind of like a swimming pool. We found the employees to be incredibly friendly and welcoming. Amara Cay is a sister facility to Pelican Cove so you do get access to their resort as well as Postcard Inn. 

What we loved about Amara Cay:

  • Walking distance to Lazy Days, a popular restaurant & great place to grab drinks 
  • Employees were super nice 
  • Nice pool with live music, also really nice fire pits 
  • Lobby is a lively place with events and fun things to do throughout the week 
  • Pet friendly (though this could be a con to some)

Cons of the Amara Cay:

  • We found the walls were pretty thin. We heard the entire story of our neighbor’s flight experience (in case you were wondering, the flight was delayed, had a tough time getting a rental car, but finally made it).
  • Rooms were more outdated than comparable resorts in Islamorada
  • It felt very crowded. It could be a fluke and/or could have been just a random weekend that everyone decided to stick around the resort more than exploring the town. However, we have stayed at other resorts in Islamorada when they were fully booked and didn’t feel like they were crowded in the same way as the Amara Cay.
cheeca lodge in islamorada florida keys

Islander Resort

I’d heard a lot of great things about the Islander Resort before we finally got the chance to stay there. Well, I get it now. We loved everything about our stay. Upon check in, we were upgraded from a standard room to a room with a water view that came with a small kitchen area, pull out couch in one area and a king sized bed in another area. The two areas could be separated by a door if traveling with kids or other people.

Clearly Unique Charters is on site at the Islander Resort, so you don’t have to travel anywhere if you want to take a snorkeling or sandbar excursion. It is an extra cost, but it’s really nice to not have to leave the resort. The Islander Resort has two amazing swimming pools and two hot tubs. Their landscaping is also immaculate with the best tropical vibes. Florida Keys History & Discovery Center is located on site, too. It is an extra cost but we enjoyed spending about an hour there one morning.

What we like about the Islander Resort

  • Pet friendly
  • Some of the most beautiful grounds
  • Very nice pools

Cons of the Islander Resort

  • Towels in the pool area were not well stocked. The day we checked in there were no towels and we alerted employees, but they were never replaced. Since it was the day we checked in, we didn’t have access to bath towels yet either and ended up tracking water into the lobby when we went to check in since there was no way to dry off.
Islander Resort in Islamorada Florida Keys

Fisher Inn

Fisher Inn is a smaller resort. We have always spent a bit more to get the room with a full on water view and it is so worth it to us. Like Casa Morada, you cannot enter the water at this resort though it is water front. Paddle boards and bikes available for rent included in the price of your room. Another unique feature of this resort is that boat parking is included in your stay. This is hard to come by in the Florida Keys, and they also have an on site boat ramp. The pool isn’t as nice as many of the other resorts, but we don’t spend a lot of time at the pool so that didn’t bother us. Other than a complimentary breakfast, there is no food on site, but Fisher Inn is walking distance to Hog Heaven, a waterfront bbq place. 

In full disclosure, we actually had a pretty negative experience the last time we were here. I won’t bore you with the details, but ultimately we experienced poor customer service after coming across some issues. We were told that our daily service fee would be comped to make up for the issues but it never was. Before our last visit, this was our most visited resort because it was inexpensive (for Islamorada standards) and they allow dogs.

What we like about Fisher Inn

  • Prior to our last (negative) experience, this was our most visited Islamorada hotel. At the time, we were traveling to Islamorada a lot for business and found the Fisher Inn to be a cheaper option and we appreciated that it was dog friendly
  • You can bring your boat if you’re staying at the Fisher Inn

Cons of Fisher Inn

  • They have lost our reservation on two separate occasions even when we booked directly on their website. At our last visit, they had lost the reservations of the 3 people in front of us checking in, too. Luckily they always had rooms for us, but it would have been devastating if they didn’t. Islamorada is not a place you want to be without accommodations last minute as they will be very expensive.
  • We personally experienced poor customer service, though I know this can wax and wane depending on who is working
Where to stay in Islamorada on vacation

Additional resorts that come highly recommended are the Caribbean Resort and Pine and Palms, but we haven’t stayed at these two resorts yet.

Finding the perfect place to stay in Islamorada is essential for an unforgettable vacation experience. From luxurious resorts to charming boutique hotels, there is a wide variety of accommodation options to choose from. I hope this guide has helped you find the best place to stay in Islamorada for you and your loved ones.