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

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Check prices for these dates

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7 Aug - 8 Aug
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8 Aug - 9 Aug
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7 Aug - 9 Aug
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14 Aug - 16 Aug
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"The ocean view suite had a spectacular view of the basin and ocean. The location is in the middle of everything. The grounds have many private spots right on the ocean. The on site Tiki bar was enjoyable and on Sat there was a live entertainer who was very good. The pools were nice but would be better if cooled. They are remodeling and it was very loud when we arrived on Fri. The associate at the front desk, Jasmine, was professional, responsive, and friendly. She investigated and texted us to let us know it would stop by 5p and not continue until Monday. The room didn't have towel rods or hooks and no wall art. Felt recently remodeled without final touches. These are the only reasons I didn't give it a 5. I would go back."
Theron 1-night trip
Posted 9 hours ago
Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"We had a great stay at the Waterside suits and marine ."
Lynn 2-night trip
Posted 1 day ago
Waterside Suites & Marina
La Jolla Resort

La Jolla Resort

10/10 Excellent
"LaJolla was great with so many amenities. We really enjoyed our stay here."
Linda 3-night trip
Posted 4 days ago
La Jolla Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"El lugar es excelente ,bien limpio y renovado"
Jesus 2-night trip
Posted 4 days ago
Pines & Palms Resort
The Islands of Islamorada

The Islands of Islamorada

10/10 Excellent
"Very helpful staff and all amenities are in excellent usable condition. The villas and the suites are very comfortable with beautiful comfortable bathrooms."
Lila 3-night trip
Posted 4 days ago
The Islands of Islamorada
Sunset Inn

Sunset Inn

10/10 Excellent
"We greatly enjoyed our stay at the Sunset inn! the Pool was nice and clean, with enjoyable music playing in the common area. The A/C was always cold which was perfect this time of year. We would definitely stay here again for a perfect long weekend."
amanda 3-night trip
Posted 5 days ago
Sunset Inn
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"The check in staff was amazing and helpful. There was a lot of included things to do that were really nice and easy to access. There was a strong fish smell, but that was likely because people catch/clean their fish at the dock and there was a bit of sea grass along the shore that likely contributed. We'd stay there again for sure!"
Melissa 2-night trip
Posted 5 days ago
La Siesta Resort & Villas

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