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

Beach Hotels & Resorts in Upper Matecumbe Key from NZ$165

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Check availability on Upper Matecumbe Key Beach Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Upper Matecumbe Key beach hotels

A beach with palm trees and lounge chairs.
A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Unwind on Islamorada's private white sand beach with loungers, boat tours, and spectacular sunset views just steps away
NZ$380
includes taxes & fees
24 Sept - 25 Sept
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.
A bathroom with a marble floor, a wooden vanity, a toilet, and a shower curtain.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

2. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Sink your toes in soft sand steps away from this beachside resort with private marina.
NZ$165
includes taxes & fees
29 Sept - 30 Sept
Breezy Palms Resort
A view from a window overlooking a beach with palm trees and a wooden pier.
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.
A balcony with two white cups on saucers, overlooking a beach with palm trees and the ocean.

3. Casa Morada

Casa Morada
Matecumbe
  • Escape to a serene beachside sanctuary with complimentary kayaking and a short drive to pristine white sands with loungers and umbrellas.
NZ$328
includes taxes & fees
19 Oct - 20 Oct
Casa Morada
A beach with palm trees, a wooden pier, and beach chairs.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

4. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Unwind where the Florida Keys meet paradise: private beach bliss with water sports, yoga, and endless ocean adventures.
NZ$327
includes taxes & fees
23 Sept - 24 Sept
Pines & Palms Resort
A beach with lounge chairs, kayaks, and a wooden pier.
A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.
A modern living room with a dark brown sofa, a coffee table, and a blue lamp. There is a kitchen area with a microwave and a coffee machine. A painting of a beach scene is on the wall.
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

5. Drift Hotel

Drift Hotel
Key Largo
  • Experience waterfront bliss with direct beach access, kayaking adventures, and sandy shores perfect for unwinding in the Florida sun.
NZ$204
includes taxes & fees
27 Sept - 28 Sept
Drift Hotel
A beach with palm trees, lounge chairs, and a view of the ocean.
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A covered outdoor area with a view of a beach and palm trees.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

6. Rock Reef Resort

Rock Reef Resort
Rock Harbor
  • Seaside adventure on a private sandy beach with kayaking, beach towels, and a sun-drenched outdoor pool for coastal relaxation.
NZ$182
includes taxes & fees
29 Sept - 30 Sept
Rock Reef Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A wooden dock extending into calm water, with tables and chairs under umbrellas, and a thatched-roof building in the background.
A balcony with two chairs and a small table, overlooking a body of water and greenery.

7. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
  • Relax by the marina, offering easy beach access with free shuttle to private beach club.
NZ$231
includes taxes & fees
29 Sept - 30 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.
A sunset over a calm body of water with a dock and lounge chairs.
A bakery display case with various muffins and frittatas labeled with flavors like blueberry, cranberry orange, banana walnut, chocolate, egg cheese vegetable fritta, egg sausage fritta, and egg cheese fritta.
A pathway lined with palm trees and a speed limit sign of 5 MPH.

8. Seafarer Key Largo

Seafarer Key Largo
Rock Harbor
  • Experience Key Largo's soothing seaside charm with a private beach, hammocks under swaying palms, and breathtaking sunset views.
NZ$214
includes taxes & fees
5 Oct - 6 Oct
Seafarer Key Largo
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.
A balcony with a view of the sea, a beach, and a thatched hut.
A room with a view of a beach, a balcony with a railing, and a door leading to the outside.
A round glass table with a decorative plate, surrounded by wicker chairs with floral upholstery. A large window offers a view of a beach and palm trees.

9. Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo
  • Embrace the coastal escape at this hotel with free cabanas and loungers on its private beach, perfect for watching spectacular sunsets.
NZ$230
includes taxes & fees
24 Sept - 25 Sept
Sunset Cove Beach Resort
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.

10. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
NZ$299
includes taxes & fees
24 Sept - 25 Sept
Kona Kai Resort and Gallery - Adults Only
View all properties

Choose what matters most at beach hotels in Upper Matecumbe Key

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Upper Matecumbe Key Hotel Reviews

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
Debra 3-night trip
Posted less than an hour ago
Breezy Palms Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"
Olga 2-night trip
Posted 2 hours ago
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel."
Julia 1-night trip
Posted 6 hours ago
Chesapeake Beach Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Todo perfecto solo q en los Restaurantes no hay desayuno incluido, y los Plato’s están por en ima de la media de sus precios y en realidad no vale la pens pagarlos en ima de eso se demoran mucho"
Raul 2-night trip
Posted 8 hours ago
Playa Largo Resort & Spa, Autograph Collection
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

8/10 Good
"All was great, we just had an issue with a food item we ordered twice and was incorrectly doubled charged in both occasions. It looked liked a POS system issue, and the staff quickly resolved it. Other than that, everyone and everything was great. The resort is paradise by the beach ⛱️ 💯"
Luciana 1-night trip
Posted 8 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Casa Morada

Casa Morada

10/10 Excellent
"Very helpful staff and great location"
David 1-night trip
Posted 8 hours ago
Casa Morada
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"The Pelican is a darling spot! Lots of space, convenient parking right next to our door, beautiful sandy beach area, well maintained dock, plenty of comfy Adirondack chairs in multiple spots to watch the water - the boats, fish, birds, and manatees. We really enjoyed the use of kayaks as well. Just a lovely property and stay."
Heidi 1-night trip
Posted 23 hours ago
The Pelican Key Largo Cottages
Islander Resort

Islander Resort

10/10 Excellent
"Nice pool"
Henry 1-night trip
Posted 1 day ago
Islander Resort
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel."
Miladis 2-night trip
Posted 1 day ago
Hawks Cay Resort

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