Find Beach Resorts in Upper Matecumbe Key, FL
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21 Aug - 23 AugOur top choices for Upper Matecumbe Key beach hotels
1. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Unwind on Islamorada's private white sand beach with loungers, boat tours, and spectacular sunset views just steps away
£162
includes taxes & fees
8 Sept - 9 Sept
2. Breezy Palms Resort
Breezy Palms ResortMatecumbe
- Sink your toes in soft sand steps away from this beachside resort with private marina.
£122
includes taxes & fees
10 Aug - 11 Aug
3. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Unwind where the Florida Keys meet paradise: private beach bliss with water sports, yoga, and endless ocean adventures.
£187
includes taxes & fees
30 Aug - 31 Aug
4. Casa Morada
Casa MoradaMatecumbe
- Escape to a serene beachside sanctuary with complimentary kayaking and a short drive to pristine white sands with loungers and umbrellas.
£121
includes taxes & fees
31 Aug - 1 Sept
5. Rock Reef Resort
Rock Reef ResortRock Harbor
- Seaside adventure on a private sandy beach with kayaking, beach towels, and a sun-drenched outdoor pool for coastal relaxation.
£99
includes taxes & fees
30 Aug - 31 Aug
6. Drift Hotel
Drift HotelKey Largo
- Experience waterfront bliss with direct beach access, kayaking adventures, and sandy shores perfect for unwinding in the Florida sun.
£102
includes taxes & fees
10 Aug - 11 Aug
7. Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
- Relax by the marina, offering easy beach access with free shuttle to private beach club.
£105
includes taxes & fees
2 Sept - 3 Sept
8. The Pelican Key Largo Cottages
The Pelican Key Largo CottagesKey Largo
- Escape to paradise with a private sandy beach where breathtaking sunsets and tropical tranquility meet Florida's coastal charm.
£78
includes taxes & fees
12 Aug - 13 Aug
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Top Upper Matecumbe Key Hotel Reviews
Lime Tree Bay Resort
10/10 Excellent
"Very nice stay at the Keys"
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."
Waterside Suites & Marina
10/10 Excellent
"We had a great stay at the Waterside suits and marine ."
La Jolla Resort
10/10 Excellent
"LaJolla was great with so many amenities. We really enjoyed our stay here."
Pines & Palms Resort
10/10 Excellent
"El lugar es excelente ,bien limpio y renovado"
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!"
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