The Best Beach Hotels in Upper Matecumbe Key, FL from ₩113,589 in 2025

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Top Upper Matecumbe Key Beach Hotels

Relax on the beach with lounge chairs and umbrellas at La Jolla Resort.

"I love staying here! Old Florida charm and convenient to great restaurants!"

₩192,432 total

includes taxes & fees

Aug 14 - Aug 15

Relax on the beach with a tranquil ocean view and comfortable sun loungers.

"The hotel is wonderful "

₩314,270 total

includes taxes & fees

Aug 10 - Aug 11

Relax on the beach with a clear view of the ocean from a wooden pier, surrounded by palm trees and comfortable lounge chairs.

"Wonderful stay. Amazing desk staff upon arrival. "

₩328,424 total

includes taxes & fees

Aug 17 - Aug 18

Relax in comfort on the beach with lounge chairs and enjoy the ocean views.

"Beautiful location loved the rooms and restaurants were excellent "

₩418,924 total

includes taxes & fees

Aug 11 - Aug 12

Relax on the beachfront lawn with lounge chairs, enjoy the tranquil atmosphere, and take in the views of the calm sea.

"Best kept secret, love staying here,!"

₩199,806 total

includes taxes & fees

Aug 19 - Aug 20

Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

"Great hotel a family room "

₩354,961 total

includes taxes & fees

Sep 1 - Sep 2

Relax by the uniquely shaped pool surrounded by palm trees and shaded by umbrellas.

"Fantastic staff working there. Incredibly friendly and helpful. Very clean rooms and loved being able to take the water taxi to the 2 other resorts "

₩323,306 total

includes taxes & fees

Sep 1 - Sep 2

"The villas were nice and relaxing but the association with the islander resort made to stay great. "

₩430,305 total

includes taxes & fees

Sep 1 - Sep 2

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept"

Cheeca Lodge & Spa

10/10 Excellent

"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other things to do outside of the resort, bikes are available to get around locally. Rooms were clean and comfortable. The rooms on the ocean were recently remodeled. The property is beautiful and easy to navigate. Oceanside live music at night was really nice, lots of families congregated on the beach to enjoy the ocean breeze and entertainment."

Breezy Palms Resort

10/10 Excellent

"Owner/manager was terrific. Walls are thin- could hear neighbor snoring Bummer that smoking was allowed on and near the jetty. Pool.was busy and family oriented but pleasant and clean. Cool vanity in bathroom- albeit there seemed to be a former medical stand being used as furniture in living room. Great to have kitchen area. IM is an expensive area for going out a lot."

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Top Upper Matecumbe Key Beach Hotels