Best Resorts in Islamorada For Every Type of Traveler

If it’s your first time visiting the Florida Keys, finding a place to stay can be a little overwhelming.

Lucky for you, we have stayed almost everywhere in Islamorada, so we can give you the lowdown on all of the best resorts in Islamorada no matter what type of accommodation you are looking for.

In this article, I include YouTube videos of some of the resorts we’ve stayed at in Islamorada. If you watch any of them, if you want to watch any of them, or if you like them/find them helpful and want to support our YouTube channel, it would mean so much if you could subscribe.

In Islamorada, there are no all inclusive resorts. All resorts in this article have at least one outdoor swimming pool. Most include things like bikes, kayaks, and stand up paddle boards on site. And last, all of them have a daily resort fee.

The quick version of Islamorada Resorts

Don’t have time to read the entire article? Here is the highlight reel on some of my favorite Islamorada resorts:

Cheeca Lodge and Spa

There is a lot to love about Cheeca Lodge & Spa and it’s probably one of the most recommended resorts in Islamorada. Cheeca is my favorite option for luxurious accommodations in Islamorada. We loved our stay here. There is plenty to do in the area. But if you like taking it easy and just enjoying the resort, you won’t feel guilty for doing that here.

Cheeca Lodge has several restaurants on site, including fine dining, pizza and pasta, sushi, and a tiki bar (actually, two tiki bars). They also have room service. And these aren’t just restaurants you eat at just because you don’t feel like leaving, they’re actually delicious. Their sushi restaurant (Nikai) is one of my favorite sushi restaurants of all time.

The hotel is also located on 27 acres. There are adult pools, family pools, a golf course, and a spa. The golf course and spa are an additional charge.

Some of their rooms even have private balconies with a soaking tub overlooking the water. These rooms are incredible (and on my Islamorada bucket list) but when we stayed, it was at the height of busy season so we couldn’t justify the price. We plan to return when it’s a little more affordable.

Like many resorts in the Florida Keys, you can enjoy plenty of water sports such as snorkeling, kayaking, biking, and boating. Some of these activities are and extra charge, but all conveniently located on site.

Finally, Cheeca Lodge is walking distance to Cafe Moka, my favorite place to grab coffee in Islamorada and the Florida Keys Brewing Company. Both are must-visits for us every time we are in Islamorada.

And Cheeca Lodge has a shuttle that will bring you anywhere within a one-mile radius. This might not sound very far, but Islamorada isn’t very big so the shuttle will take you almost anywhere you’d want to go within Islamorada.

Why we love Cheeca Lodge and Spa

• Ease of getting around – not only are two of our favorite places walkable (the coffee shop and breweries) but the complimentary shuttle makes it easy to get all around Islamorada
• The on site restaurants are not only convenient but delicious. People come to eat at the restaurants at Cheeca Lodge even when they are not staying there.
• The grounds are immaculate. Everything from the tropical foliage and palm trees to the pools capture the essence of vacation in the Florida Keys perfectly.
• Our room was large, bright, and airy. We loved it and we were in the cheapest room.
• Golfing and spa are on site.

Cons of Cheeca Lodge

• It’s expensive

Here is a video on Cheeca Lodge:

Casa Morada

Casa Morada is the most unique place we have stayed in Islamorada. It’s a boutique hotel that only has 16 rooms so it’s very quiet and romantic. No kids under the age of 16 are allowed here.

Casa Morada is waterfront but does not have a beach area. It does have an outdoor pool that’s kind of its own island. Also, even though it is waterfront, not all rooms have a water view. Some of the rooms that are farther away actually have a decent walk to the water. But the entire area is landscaped and gorgeous; it is very tranquil, so you won’t mind.

Why we love Casa Morada

• It’s very romantic and quiet
• Staff is very nice and they get to know you since it’s such a small hotel
• Every room is different
• Location is perfect for biking to nearby attractions. It’s very close to some of our favorite places including Loralei’s (a must for dinner with a view), Cafe Moka (coffee), and both breweries (Islamorada Beer Co. and Florida Keys Brewing Co.) The bikes are included when you stay at Casa Morada.

Cons of Casa Morada

• If you have young kids in your group, you can’t stay here.
• No beach
• Some of the rooms are located a walk away from the water.
• The pool is very nice, but some of the other resorts have nicer pools

Here is a tour of Casa Morada:

Three Waters Resort and Marina

This resort is coming soon. It is the redevelopment project of the Postcard Inn Beach Resort & Marina and Pelican Cove Resort & Marina – they were two separate sister resorts. It’s undergoing renovations with an expected open date of August 2024 so we have not stayed there yet. Even though we haven’t stayed there, it’s included on this list because we stayed there when the resort was the Pelican Cove. We had a great experience and that was before the renovations, so I’m sure this will be a resort worth visiting once it’s open.

We have reservations there shortly after their grand re-opening, so I’ll be sure to update after we stay.

Chesapeake Beach Resort

Chesapeake Beach Resort is fairly recently renovated. When we visited, they were still doing construction so only half of the resort was open at the time. We stayed in a room that had ocean views and the views were absolutely incredible (the turquoise water in the Florida Keys is indescribable). We also had a great view of the Islamorada sandbar, so it was fun watching all the boats come and go.

They have a pool and a hot tub. The hot tub really is nice in the cooler months. Chesapeake Beach Resort does have a private beach for guests as well. Kayaks, paddle boards, and fishing rods are available to rent but aren’t included in the price of your stay like it is at some of the other resorts.

Last, Chesapeake Beach Resort is pet-friendly.

What we love about Chesapeake Beach Resort

• Walking distance to Wahoo’s, which is a bar and restaurant right on the water with incredible views. It is also a working marina with snorkeling, sandbar, and fishing charters running daily (did you know that Islamorada is the sport fishing capital of the world?) Actually, the marina has a charter for almost any type of boating activity you could ask for.
• If you book a room with a water view, you will be obsessed with the views – they are absolutely incredible.
• It’s recently renovated.

Cons of the Chesapeake Beach Resort

• While this can be true of any place you stay, the walls are fairly thin so if you don’t have good neighbors, noise might be an issue.
• If you don’t have a water view, the resort isn’t anything too special.
• Kayaks, paddle boards, and fishing rods are available to rent but aren’t included in the price of your stay like it is at some of the other resorts.
• I think we need to stay here again to give it a fair review. This would not be my first choice to return to. Our stay was fine and the views were some of my favorite, but it just didn’t do it for me and I’m not entirely sure why.

Amara Cay

Amara Cay has a lot of amenities and they also have daily activities. When we stayed, we enjoyed games and live music but they have different activities every week. They’re always changing so you never know what you might find.

Amara Cay also has a shuttle anywhere within a four-mile radius. You can also enjoy bikes, kayaks, paddle boards, and lawn games. They have an on-site restaurant, Reelcatch, which serves a little bit of everything like burgers and seafood. I wouldn’t go out of my way to eat at this restaurant but it’s really convenient to not have to leave the resort if you don’t want to.

I loved the pool at Amara Cay. The last time I was there, they had someone playing steel drums in the pool area. Laying by the pool while listening to steel drums play is the ultimate vacation vibe. It’s also within walking distance to Lazy Days, an iconic Islamorada restaurant right on the water.

Amara Cay doesn’t really have a beach area. Technically, you can get in the water but you probably won’t want to. You enter in kind of a drop off-type area via ladder.

Amara Cay is a sister facility to Three Waters Resort & Marina as well, so you have access to their facility if you are interested in resort hopping. Amara Cay is pet friendly.

What we loved about Amara Cay:

• Lazy Days (a popular waterfront restaurant) is in walking distance
• Everyone who worked there was friendly and welcoming
• The pool is very nice and had live music when we visited
• They have tons of events, including events for adults and also for families/kids

Cons of the Amara Cay:

• This seems to be kind of a recurring theme for resorts in Islamorada, but the walls were pretty thin. I promise we aren’t too picky. And while the walls are thin, it’s never really been an issue – we can hear full conversations, but we’ve never had a situation where they stay up all night partying or anything like that.
• Rooms were fine, but a bit more outdated compared to other resorts in Islamorada.
• Overall, this resort was great. While I can’t exactly pinpoint why, I don’t think it would be my first choice to return to. Once our kids get older, I do think this would be a great place for them, especially with all of the events.
• There is technically a beach but it’s not great. If you want to use the beach area, you enter via ladder.

Islander Resort

We loved pretty much everything about our stay at the Islander Resort. But in full disclosure, we had a water view that was incredible. Our room also had a small kitchen area and a separate living area. I could have stayed here forever.

They have food on site and it’s not a restaurant I’d go out of my way to eat at, but it’s so nice to not have to leave the resort if you are hungry but don’t want to leave.

Clearly Unique Charters is a charter company that runs out of the Islander Resort. So if you want to go snorkeling or to the sandbar, you can book a charter without having to leave.

They also have two amazing pools and two hot tubs. The landscaping throughout the (very large) property is immaculate.

The Florida Keys History and Discovery Center is also located on the Islander Resort. It’s an extra cost, but it’s a fun way to learn more about the Florida Keys and it would also be a good rainy day activity.

The Islander Resort is pet friendly.

What we like about the Islander Resort

• Pet friendly
• A lot of work has been put into the immaculate grounds
• Pools were stunning
• On site food
• Option to book a charter that leaves directly from the resort

Cons of the Islander Resort

• It was honestly hard to come up with cons for this resort. The only thing we experienced is that we weren’t able to check in on time, so we used the pool. But the pool towels were not stocked so we had no way of drying off before going back to the lobby to check in.

Here is a video on the Islander Resort:

Fisher Inn

The Fisher Inn Resort & Marina is a smaller resort. Out of all of the resorts in Islamorada, this is the one we have stayed at the most. That’s because there was a period of several months that we were traveling to Islamorada for my husband’s job and the Fisher Inn is dog friendly plus the most budget friendly option while still having some amenities.

As you know, Islamorada doesn’t exactly have cheap resorts. But the Fisher Inn is budget friendly for Florida Keys standards. Their amenities aren’t quite as luxurious as some of the other resorts but it does have pretty much everything.

They have a wide open sandy area with comfortable sun loungers, but there is no beach despite its waterfront location (this is quite normal in Islamorada, so it’s not their fault but good to know before you book). They do have paddle boards and bikes available for use during your stay.

For boaters, this is a great resort because they actually have boat parking that is included in your stay and they have a boat ramp. This can be very hard to find in the Florida Keys.

They serve simple breakfast but otherwise don’t have food on site. But Hog Heaven is a delicious waterfront BBQ restaurant and it’s a short walk (or you can use one of their bikes) from the resort.

We actually had a poor customer service experience there the last time we stayed so we haven’t been back. I’m not sure if we’ll be back because frankly there are plenty of places in Islamorada that you can stay. But I’m still mentioning it here because it’s a good budget option.

What we like about Fisher Inn

• More budget friendly than other Islamorada resorts while still being pretty nice.
• You can bring your boat if you’re staying at the Fisher Inn.
• Waterfront rooms have incredible views. You also have a great view of the Islamorada sandbar and I love watching the boats come and go.

Cons of Fisher Inn

• As I mentioned above, we had poor customer service here the last time we visited. They had an opportunity to correct it and didn’t several times. I won’t bore you with the details, but we are pretty laid back so it wasn’t an unreasonable expectation. The experience was poor enough that we haven’t been back since even though we tend to be loyal to places we enjoy and had stayed here more than anywhere else in Islamorada.

Hadley House

The Hadley House is a sister property to the Fisher Inn and the pros/cons there are very similar. It’s average price makes it a more budget-friendly option and like the Fisher Inn, it is waterfront but doesn’t have beach access.

We stayed in a 2-bedroom room because there were 5 of us, so our room was pretty nice. The 2-bedroom options have full kitchens which was also perfect for us since we were traveling with a baby (aka tons of bottles and we loved having the dishwasher).

Overall, the Hadley House was fine and the views were incredible (if you have a water view). I would stay here again if it was cheaper than other options but otherwise it wouldn’t be a top choice. Especially if I didn’t get a waterfront room.

It’s a no-frills type of place and it was perfect for our one night stopover in Islamorada on the way to Key West but if I was headed to Islamorada for vacation, I would want something a little nicer.

You can see a brief tour of our two bedroom stay at Hadley House here:

There is a resort for you in Islamorada no matter what you are looking for. From a romantic getaway to a family vacation, there is something for you. Islamorada is one of the best places to vacation and finding the right resort will make it even better. Hopefully this article helped you narrow down which resort is your best fit so you can have a great stay in Islamorada.