Find Hotels with a Pool in Upper Matecumbe Key, FL
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30 Oct - 1 NovOur top choices for Upper Matecumbe Key hotels with a pool
1. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
AED 717
AED 1,075 total
includes taxes & fees
15 Nov - 16 Nov
2. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
AED 521
AED 793 total
includes taxes & fees
20 Oct - 21 Oct
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
AED 621
AED 968 total
includes taxes & fees
19 Oct - 20 Oct
4. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
AED 465
AED 627 total
includes taxes & fees
18 Oct - 19 Oct
5. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
AED 539
AED 875 total
includes taxes & fees
29 Oct - 30 Oct
6. Hadley Resort and Marina
Hadley Resort and MarinaMatecumbe
- Dive into coastal bliss with a private beach, marina, and refreshing pool for aquatic adventures.
AED 526
AED 711 total
includes taxes & fees
9 Nov - 10 Nov
7. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
AED 757
AED 1,054 total
includes taxes & fees
21 Oct - 22 Oct
8. La Siesta Resort & Villas
La Siesta Resort & VillasMatecumbe
- Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
AED 511
AED 843 total
includes taxes & fees
16 Nov - 17 Nov
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Top Upper Matecumbe Key Hotel Reviews
Bayside Inn Key Largo
10/10 Excellent
"Really nice restaurant next to it , you get 10% discount when you stay at hotel."
Baker's Cay Resort Key Largo, Curio Collection by Hilton
10/10 Excellent
"Staff was very attentive and provided great service! Checked out at 11:00am and were allowed to stay until late afternoon. They had showers and towels we could use next to the Dry Rocks bar and grill to clean up before needing to drive back to Miami for the evening."
Chesapeake Beach Resort
10/10 Excellent
"Excellent location we had a Waterview room, which was extremely clean well maintained with a beautiful view of the ocean and beach from our balcony. Both swimming pools were well maintained. Only glitch was hot tub was not working.. would definitely stay again ."
Breezy Palms Resort
10/10 Excellent
"This property is a nice old Florida style hotel with a nice pool, a small beach and marina. The room was very clean and comfortable with a strong air conditioner. Islamorada it’s still hot in October. We got the room with ocean view and a kitchen. Is a spacious space with a pretty nice stove, lots of utensils, dishes, cups, cutlery, pans and appliances like a toaster, a drip coffee maker (all’americana machine) it even had a blender! It had a few frying pans, bowls for salad, a colander, pots for pasta with the steamer, I think it lacked a water jug because water is potable in the Florida keys and I hate buying plastic bottles, but I’m not complaining because I used the blender vase to chill water and the glass pot, the coffee carafe, too. On top of everything, this room also has two ice cubes trays. The room we got has everything you need in the kitchen. We didn’t really cooked but brought a small bottle of olive oil to make breakfast with eggs, toasts or sandwiches in the morning. Very close is CAO bakery and we had a very good Cuban espresso there every day."
Islander Resort
10/10 Excellent
"Very nice experience and cosy hotel in the Keys, super recommended!"
Lime Tree Bay Resort
10/10 Excellent
"What to say really. We had a n absolute nightmare of a day on our way down to the hotel. We were due to land at Key West at 1200 but that turned into landing in Miami and then an 8 hour delay before finally touching down. The staff at the hotel were great contacting us throughout the day and being so friendly and attentive! We arrived finally at the hotel at 2230 and Robin at the check in was so fantastic staying back for us to be able to be checked in! We even got an upgrade. The only downside was due to the mess caused by flights, we were in the room for just a few hours. The resort was beautiful. The view from The balcony to the sea. The room was just so unbelievable it was like the stuff you get in dreams. Such a beautiful resort, beautiful room and I am certain we will be back! Thank you!"
Hadley Resort and Marina
8/10 Good
"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."
Waterside Suites & Marina
10/10 Excellent
"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."
La Jolla Resort
10/10 Excellent
"It was quaint and right on the water"
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