The Best Hotels with a Pool in Upper Matecumbe Key, FL from AED 457 in 2026

Check availability on Upper Matecumbe Key Hotels with a Pool

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Our top choices for Upper Matecumbe Key hotels with a pool

Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

AED 953 total

includes taxes & fees

8 Jun - 9 Jun

Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Matecumbe

Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.

AED 1,122 total

includes taxes & fees

8 Jun - 9 Jun

Cheeca Lodge & Spa

Matecumbe

Tropical paradise swim experience awaits with three refreshing pools and poolside service.

AED 1,091 total

includes taxes & fees

2 Jun - 3 Jun

Islander Resort

Matecumbe

Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.

AED 1,178 total

includes taxes & fees

18 Jun - 19 Jun

La Siesta Resort & Villas

Matecumbe

Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.

AED 1,027 total

includes taxes & fees

14 Jun - 15 Jun

Bayside Villas by Islander Resort

Matecumbe

Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.

AED 1,019 total

includes taxes & fees

3 Jun - 4 Jun

Breezy Palms Resort

Matecumbe

Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.

AED 457 total

includes taxes & fees

28 May - 29 May

Casa Morada

Matecumbe

Dive into a blissful pool oasis in the Florida Keys with a poolside bar and sunny loungers to unwind from adventure.

AED 1,133 total

includes taxes & fees

1 Jun - 2 Jun

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Breakfast included

4 stars

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

8/10 Good

"Hotel is Being sold at the moment- Dirty dishes left alllll week in our hallway seemed odd- never picked up… Lightbulbs not working in room needed to be replaced Just a bit off with service it felt disconnected"

Baker's Cay Resort Key Largo, Curio Collection by Hilton

6/10 Okay

"I stayed here in 2022 and the rooms were clean. This time around the rooms were not that clean. The towels were old and stained. The sheets had holes. It didnt feel clean. The windows had prints on them. The food at the restaurant was good. The service was good. The cleanliness declined..."

Marina Del Mar Resort and Marina

10/10 Excellent

"The room was excellent, great layout. The 1/2 wall sliding glass opening to the large balcony and walkway was a pleasant surprise. The look over the Marina was awesome, the boat traffic was an unexpected highlight…We got lucky with the covered parking more often than not.. The bar & restaurants next door were very lively, good food and times for sure.. The only draw back was the fine black sand/dust, which is resident of being in the Keys… you had to wash your feet before going to a very comfortable king bed. Will definitely book again next time down to the Keys!!"

Hawks Cay Resort

4/10 Poor

"Let’s start by saying I gave them months in advance that we were coming and plans and they managed to not fulfill their part of the deal. I paid for extra amenities to be delivered to the room before we got there for my in-laws 52nd anniversary. they fixed it still charged me ice machine didn’t work neither the vending machine, which would’ve been cheaper to buy a soda out of the machine every once in a while, a good way to make sure you go to the bar and spend way more money the Customer Service in the café store unbelievably terrible the weight staff all, but one gentleman had no compassion or care didn’t understand the food we were ordering and please don’t expect to sit outside in the morning when others are outside eating and get service that’s a bad idea. Don’t sit in a table without a menu you won’t get service for some reason. They don’t put menus on the tables if you’re sitting there in the morning waiting for service when you do go to the front desk to express your concerns they act like they care about everything and do nothing about it, including all of the miscellaneous hidden charges that racked up my bill over $1200. You can’t leave an open tab at the Bar. You have to pay for each drink separately and they expect you to tip every time if you’re not a big wig if you don’t have money flowing out of your ears, don’t expect great bar service or table service near the bar. Do you have to complain to Simon the manager to get a little bit better service."

Bayside Inn Key Largo

8/10 Good

"The view of the bay was spectacular & paddle boards were fun. Things that weren’t great: The pool was very cloudy & not clean. Our shower barely had any pressure, the safe didn’t work and we didn’t have a luggage stand to place our luggage on. We really enjoyed our stay, but the little inconveniences just added up. The staff there is very nice."

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Check availability on Upper Matecumbe Key Hotels with a Pool

Our top choices for Upper Matecumbe Key hotels with a pool

Chesapeake Beach Resort

Amara Cay Resort

Cheeca Lodge & Spa

Islander Resort

La Siesta Resort & Villas

Bayside Villas by Islander Resort

Breezy Palms Resort

Casa Morada

La Jolla Resort

Sunset Inn

Choose what matters most at hotels with a pool in Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Islander Resort

Amara Cay Resort

Bayside Villas by Islander Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Marina Del Mar Resort and Marina

Hawks Cay Resort

Bayside Inn Key Largo

Breezy Palms Resort

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Upper Matecumbe Key Hotels by Star Rating

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Find Hotels with a Pool in Upper Matecumbe Key, FL

Change your mind

Treat yourself

Be picky

Check availability on Upper Matecumbe Key Hotels with a Pool

Our top choices for Upper Matecumbe Key hotels with a pool

Chesapeake Beach Resort

Amara Cay Resort

Cheeca Lodge & Spa

Islander Resort

La Siesta Resort & Villas

Bayside Villas by Islander Resort

Breezy Palms Resort

Casa Morada

La Jolla Resort

Sunset Inn

Choose what matters most at hotels with a pool in Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

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More Accommodation Types in Upper Matecumbe Key

Upper Matecumbe Key Hotels by Star Rating

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