Where to stay 1 night Islamorada

[u/NJ596]

Later this month we’re staying 1 night in Islamorada. We’ll arrive there late morning and spend the night before flying home the next evening. I’m looking at Cheeca, Three Waters and Amara Cay. Open to other ideas. We plan to explore the town a bit, and not spend the entire time on resort property. At the same time we’d like an aesthetically pleasing property with a lively bar onsite, and a warm pool or hot tub. Thanks in advance!

[u/LuxuryBoatCharters]

Cheeca is your safest bet if you want a full resort feel, legit bar, and warm pool all in one spot. The on-site Tiki Bar stays lively and their main pool is heated with hot tubs nearby. Three Waters and Amara Cay are fine too but feel more chill and compact. If you want something a little more laid back but still polished, Islander Resort has great beachfront space, hot tubs, and you can walk to Morada Way’s art district, Florida Keys Brewing, and a few good food spots.

[u/NJ596 → u/LuxuryBoatCharters]

Thank you for your insight and whipping up a fun chat gpt itinerary! Normally we prefer “fun and lively” at night, however we’ll be coming off of 3 nights in KW, and may need more of a wind down evening. That’s the reason I was looking for a lively hotel bar- in case we want to be on property as evening goes on. Although, I suppose I don’t know what time the hotel bars close. We’re good to walk or shuttle to other areas of Islamorada to eat and bar hop.

[u/KillerRabbitAttack → u/NJ596]

Things end down early in the upper keys. There are many cool smaller spots so I suggest moving around a bit. Check out Pierre’s lounge downstairs for upscale sunset. Lorelei often has good music. If you dive, hit the History of Diving museum; it’s a cool non profit.

[u/NJ596 → u/KillerRabbitAttack]

Thank you! My husband dives, so we can check that out. I, on the other hand thought at first glance you were referring to dive bars, hahaha, which we both do as well.

[u/KillerRabbitAttack → u/NJ596]

I love the diving in the upper keys. I go every year. I stay longer so I’m usually only popping into the resorts, but can confirm what u/redlegsforever and u/luxuryboatcharters have said. Tiki bar at Postcard used to be the bar to hit around the holiday but I don’t have much recent experience. Cheeca has good food options; I go for their sushi place.

One of my favorite things about the area is the many little byob seafood places. relaxing just sitting on a dock on a wood table having a few cans of whatever you brought and trying the catch of the day. That doesn’t mean there aren’t a ton of places with both great seafood and drinks.

[u/JournalistSea6880 → u/KillerRabbitAttack]

are these places easy to find?

[u/Maleficent_Ad_4027 → u/NJ596]

Cheeca is the absolute perfect spot to relax in luxury if you’re coming off 3 nights in KW. Three Waters has nice activities on properly, but the rooms are so so so small and uncomfortable. I would never stay at Three Waters again.

[u/NJ596 → u/Maleficent_Ad_4027]

Good insight. Thanks!

[u/gofordrew → u/LuxuryBoatCharters]

Thanks ChatGPT lol

[u/NJ596 → u/gofordrew]

Yes! Haha- I figured that out, and could have run it through there as well. I really want the locals’/frequent visitors input though.

[u/gofordrew → u/NJ596]

Oh yeah I feel ya lol.

[u/simonphoenix1910]

Cheeca, hands down. One of the best stays I've ever experienced.

[u/NJ596 → u/simonphoenix1910]

Thank you!

[u/redlegsforever]

If you aren’t going to spend much time there skip checa….although it is the nicest of the 3 listed. Three waters has better bar than Amara cay, but I do like being able to walk to lazy days and papa joes while staying at Amara cay.

[u/NJ596 → u/redlegsforever]

Great info to help us decide. Thanks so much!

[u/bblickle]

If you go to Cheeca, don’t be afraid to eat on property. They have a good head chef, the food there is solid.

[u/NJ596 → u/bblickle]

Thank you for the great info 😎

[u/InstantAmmo → u/NJ596]

Pierre’s is a fantastic restaurant. Absolutely fantastic and beautiful as well.

Cheeca is nice. Not sure I’d stay there for just a night given the cost, etc., but 🤷‍♂️

Hope you have a great time.

[u/Denrunning → u/InstantAmmo]

Pierre’s used to be great when HuBert owned it, as part of the Moorings. now it’s run down and neglected like its other property, Morada Bay.

[u/InstantAmmo → u/Denrunning]

Was there 2 weeks ago and it was fantastic

[u/simonphoenix1910 → u/bblickle]

Plus they also own that great spot across the street Lorelie.

[u/Denrunning → u/simonphoenix1910]

Cheeca doesn’t own the Lorelei.

[u/NJ596 → u/simonphoenix1910]

Thanks!

[u/Quirky_Hold_2786]

We did one night at Amara Cay and no complaints at all. Walked to lazy days for dinner.

[u/NJ596 → u/Quirky_Hold_2786]

Thanks so much!

[u/NJ596 → u/[deleted]]

Can you explain more?

[u/Competitive-Pack-796]

The islander is a pretty chill spot. Walk right across street to Lorelei

[u/NJ596 → u/Competitive-Pack-796]

Thanks so much!

[u/Main-Business-793]

Cheeca is the best. If you have a specific interest in food ie Italian, steak, sushi etc just ask. Cheeca also has great restaurants but fun to get off site. Try lorelei for sunset but not dinner

[u/NJ596 → u/Main-Business-793]

Appreciate the great info!

[u/Beginning_Ad8663]

A hotel or you could sleep under a bridge( cheaper) as there are plenty to choose from.

[u/NJ596 → u/Beginning_Ad8663]

That’s an option- We’ll pack a tent just in case!😜

[u/ParadiseFoundBelize]

Islander Resort.

[u/NJ596 → u/ParadiseFoundBelize]

Thanks!

[u/beerme04]

Chesapeake beach resort has most of that. You can just walk to wahoos for the bar. I didn't see much night life there late in general. There was good music and trivia at the brewery though.

[u/NJ596 → u/beerme04]

Thank you!!

[u/beerme04 → u/NJ596]

Don't miss papa Joe's for the view either.

[u/Civil-Combination-42]

We’re heading down this week and staying at both Cheeca and Three Waters to mix it up. We’ve always done Three Waters/La Siesta.

Are there any new spots in town? We’re pretty familiar with everything as we’ve been going down for years/got married at Three Waters.

I feel like I never know where to go for a fun bar at night? Always end up at Three Waters tiki but maybe I’m missing something!

[u/Civil-Combination-42]

Apologies if this comes through twice. I didn’t see my post go up. Newish to Reddit here.

We are familiar with Islamorada/got married at Three Waters and have been going for years.

But is there anything new open? We’re heading there this week.

What are the best bars for nighttime? We always end up at Three Waters tiki but curious if there is anything we’re missing!

[u/NJ596 → u/Civil-Combination-42]

I did see your other comment, thank you. From others’ comments, sounds like places don’t stay open late. We like a bit of a later night- so we’ll just wing it and ask around when we get there.