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

Beach Hotels in Upper Matecumbe Key, Islamorada

  • 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 availability on Upper Matecumbe Key Beach Hotels

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

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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue chairs and a small table, overlooking a beach with palm trees and a clear blue sky.

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
P9,481
P14,197 total
includes taxes & fees
Sep 28 - Sep 29
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.
A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.
A beach with thatched umbrellas, palm trees, and lounge chairs.

2. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Sink your toes in soft sand steps away from this beachside resort with private marina.
P4,310
P5,850 total
includes taxes & fees
Sep 29 - Sep 30
Breezy Palms Resort
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.
P9,835
P11,772 total
includes taxes & fees
Oct 19 - Oct 20
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 beachside resort with a pool area, lounge chairs, and palm trees.

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.
P7,348
P11,729 total
includes taxes & fees
Sep 23 - Sep 24
Pines & Palms Resort
A beach with lounge chairs, kayaks, and a wooden pier.
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.
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 modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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.
P5,885
P7,326 total
includes taxes & fees
Sep 28 - Sep 29
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 wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

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.
P5,819
P6,546 total
includes taxes & fees
Sep 23 - Sep 24
Rock Reef Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A wooden dock extending into calm water, with tables and chairs under umbrellas, and a thatched-roof building in the background.
A resort with a pool, multiple buildings, and a waterfront view.
A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

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.
P5,593
P8,282 total
includes taxes & fees
Sep 28 - Sep 29
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 pathway lined with palm trees and a speed limit sign of 5 MPH.
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 sunset over a calm body of water with a dock and lounge chairs.

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.
P6,296
P7,966 total
includes taxes & fees
Sep 28 - Sep 29
Seafarer Key Largo
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.
A balcony with a view of a beach, palm trees, and a clear sky.
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.
P7,348
P8,267 total
includes taxes & fees
Sep 24 - Sep 25
Sunset Cove Beach Resort
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A beachside resort with lounge chairs, a pool, and palm trees.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

10. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
P7,950
P10,709 total
includes taxes & fees
Sep 28 - Sep 29
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

Explore a world of travel with Expedia