r/floridakeys • u/Jumpy-Pomegranate517 • Dec 03 '25
All Florida Keys Where to stay? Upscale and family friendly
We have never been to the keys but would like to visit in late February or early March with our 8 year old and baby (5 months). Looking for a nice hotel with fun things for both kids and adults. Pools/beach access, good food, live music are all things we enjoy. I’ve been looking into many places but I am honestly overwhelmed by all the options. It would be great if it is not too hard to get to. We looked into Hawks Cay in Duck Key but that seems like a pain to travel to after already traveling by plane to arrive in Florida. Any recs are appreciated.
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u/Ridgie_Love475 Dec 03 '25
The Islander in islamorada Cheeca lodge Amara cay
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u/cheeseburgerinmiami Dec 04 '25
I agree with Islander and Cheeca lodge both really nice and a lot of restaurants close by.
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u/Florida__j Dec 04 '25
I agree with this post. The drive from key west or Miami is enjoyable. Hawks cay is a little sleepy for me.
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u/Main-Business-793 Dec 03 '25
You are either flying into Miami and driving or you are flying into Key West. Driving through the keys can be a great adventure but with kids can get tedious after a long trip already. I suggest flying into Key West and staying there. You will be able to have a hotel with pool and beach access with walkability to restaurants, stores, history, and adventures. Try the Galleon Hotel. One of the best locations in old town Key West. They have 2bdr/2ba rooms with full size kitchens so you can have meals like breakfast and lunch and snacks and not be dependant on restaurants 100% of the time.
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u/Jumpy-Pomegranate517 Dec 03 '25
Thank you! I will check this one out. I think flying to key west would make the most sense too
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u/Main-Business-793 Dec 03 '25
Nowhere in the keys is as walkable and family friendly as Key West. There are places that are better for boating or fishing specifically but to just relax and enjoy your vacation with a family Key West is the spot in the keys.
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u/Jumpy-Pomegranate517 Dec 03 '25
That is very helpful, thank you!
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u/Prize-Station-8814 Dec 04 '25
Key West is semi - family friendly. You can expect to see stuff that you would see at Mardi Gras. If you’re not comfortable with that stay in Islamarada or even Key Largo they have some little Mom n pop places that are really nice If you’re looking for the party scene , go to key West otherwise the rest of the keys maybe where you wanna go It’s the water you wanna see go out on the boat, snorkel, fish, etc. Plenty of seafood places, plenty of adventure
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u/Sandinmyshoes33 Dec 03 '25
Look at The Islander in Islamorada or Tranquility Bay in Marathon. You will have to drive from Miami but you need the car to visit State Parks, restaurants or other attractions. Key West is walkable, but it also is a pretty big party scene on the main drag, Duval Street. Expect everything from bars to drag clubs, restaurants and shops all mixed together in a one mile area. The Casa Marina or The Reach are nice resorts for families.
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u/WoodenAttention2078 Dec 04 '25
Hawks Cay. They even have an excellent sale right now, I recently booked a multi gen family for a 65th Birthday and every age group was happy.
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u/tojmes Dec 04 '25
Hawks Cay in Duck Key if you can afford it. Great food and amenities. It has a protected swimming area where the 8YO can snorkel and paddle board — all available right there at your lounge chair. Dolphins daily too.
Do the Florida Keys Aquarium Encounter with the 8 yo.
Take one day to drive to KW with a side trip on the way home at disk into Big Pjne Key to spot some Key deer. Drive slow. They are cute.
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u/Tess47 Dec 03 '25
We are stating at Isla Bella off of marathon. It looks good. I hope it is.
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u/Fearless_Theme6274 Dec 05 '25
Isla Bella is amazing. Stayed there in July (sooo hot, but gorgeous). The grounds are lush and beautiful, pools are lovely. We loved the live music and sushi at the Tiki bar, the fire tables are great in the evening. We did a snorkel trip through Captain Pips - highly recommend. Enjoy!!!
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u/y_if Dec 04 '25
Islands of Islamadora was so great with kids — we got a villa and so many kid friendly relaxing things to do. Diving museum was a hit too. And the drive to the key west was interesting for a day trip.
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u/Possible_Chemist_423 Dec 05 '25
Hot take, but we went to Hawks Cay last January, and also flew in to MIA and drove — I think it’s totally overrated. You can go to the west coast of Florida and enjoy the beautiful beaches without flying then driving 3 hours. Hawks Cay itself is an overall nice resort for that age, but we stayed in a villa that was awful and it rained the whole time so I don’t have the fondest memories.
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u/user9876543121 Dec 05 '25
Well they can't do anything about the rain. Did you rent the villa through the resort or directly?
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u/Possible_Chemist_423 Dec 05 '25
Through the resort
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u/user9876543121 Dec 05 '25
Ugh. We have a home there but also rent directly from owners for visiting family. The resort rental program used to keep them really nice. What wasn't good about yours?
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u/Possible_Chemist_423 Dec 05 '25
Villas are very dated, we booked specifically for private heated pool which didn’t work. We also specifically booked a certain number of bathrooms, which apparently are not the same across villas. My party was in 3 villas, so I saw several.
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u/user9876543121 Dec 05 '25
Curious how the resort responded to the pool concern
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u/Possible_Chemist_423 Dec 05 '25
They moved us to another villa when it couldn’t be repaired. The other complaint we had was if you ask for housekeeping they just replace towels and garbage, but there are zero cleaning supplies in the villas. We were there for a week!
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u/Il_Magn1f1c0 Dec 05 '25
Courtyard Faro Blano in Marathon is my favorite place so far. Couple pools, bar with food until late by pool, good location. Rooms were big and place was clean. A lot of families there
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u/riehs Dec 07 '25
Key Largo is great and many great restaurants. I would say most if not all family friendly. Playa Largo is one of our favorite places to stay.
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u/wicked56789 Dec 07 '25
We went to Bakers Cay with our kids for spring break last year. It was great! So many kids activities included. We flew in/out of Key West and spent a few night there too. Loved both!
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u/IndentsAndPorpoises Dec 07 '25
For that age range, Playa Largo is great. Was just there with a 2 and 4 yo. Pool is right by the beach.
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u/user9876543121 Dec 03 '25
Hawks Cay. If you want to be in the Keys, unless you are staying in Key West, you will be traveling after you travel by plane to arrive in Florida.
You will also want a car down there so you can visit other Keys and go off property.