Upper Matecumbe Key Resorts

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Upper Matecumbe Key resorts

Cheeca Lodge & Spa

Matecumbe

David

RM1,215 total

includes taxes & fees

2 Aug - 3 Aug

Amara Cay Resort

Matecumbe

Leidys

RM1,073 total

includes taxes & fees

16 Aug - 17 Aug

Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

La Siesta Resort & Villas

Matecumbe

Cassandra

RM1,011 total

includes taxes & fees

20 Aug - 21 Aug

Premium bedding, in-room safe, laptop workspace, iron/ironing board

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

CATHY

RM1,253 total

includes taxes & fees

10 Aug - 11 Aug

Lime Tree Bay Resort

Long Key

JACLYN

RM744 total

includes taxes & fees

16 Aug - 17 Aug

Matecumbe Resort

Matecumbe

Kathleen

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Edgar

RM1,436 total

includes taxes & fees

18 Aug - 19 Aug

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

Key Largo

xiomara

RM1,505 total

includes taxes & fees

11 Aug - 12 Aug

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

10/10 Excellent

"Fantastic hotel, great for family trips. Outstanding service, great pool. Restaurant good but not the best. I’ll stay again."

Hadley Resort and Marina

10/10 Excellent

"Lo único que no nos gustó es que en el área de la piscina no encontramos baños,el resto del hotel estuvo maravilloso y aún más el trato recibido por la muchacha del front desk y también del front desk el señor jamal,ambos maravillosos El desayuno muy bueno y la general todo muy bien,gracias"

Bayside Villas by Islander Resort

10/10 Excellent

"The Bayside Villa's Were a great place to stay. The only downside is there's no lobby onsite, we had to check in at another location. Also, we had an issue with our refrigerator which resulted in no ice and there isn't an ice machine on the property. It was minor so all in all it was excellent."

Chesapeake Beach Resort

8/10 Good

"We just ended a three night stay here. The property is cute. The rooms were cute and clean. The complementary breakfast was surprisingly delicious. The beach was covered in seaweed and not really raked up. They were doing maintenance on the main pool so unfortunately one of the days we could not use it. It was super noisy in the morning and we were not given a heads up when I sent a text, I got a standard general response, letting me know that a text was sent, but it looked like it never went through. I feel like at check-in. This should’ve been something that was communicated especially when you’re going down for a relaxing peaceful weekend. We spent one of the mornings eating our breakfast listening to loud work being done at the pool directly next to us. Thursday night was cheap but for the price of Friday and Saturday night and how high it was this is something that definitely should’ve been communicated. We were down with family, so there were two other rooms that were booked as well and they all felt the same. When we checked in the two girls didn’t tell us much about the property. My fiancé had asked if he could cut off a band that was on his arm and she looked at him like he had five heads. It was a weird encounter. The food at the tiki hut was extremely expensive and not good whatsoever. However, the drinks were delicious and the guy who made them was wonderful."

Find out more about Upper Matecumbe Key