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

Find Beach Resorts in Upper Matecumbe Key, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key Beach Resorts & Hotels

Tonight
4 Sept - 5 Sept
Tomorrow
5 Sept - 6 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Upper Matecumbe Key beach hotels

A beach with palm trees and lounge chairs.
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.
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.

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
£133
includes taxes & fees
5 Oct - 6 Oct
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 beach with thatched umbrellas, palm trees, and lounge 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.

2. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Sink your toes in soft sand steps away from this beachside resort with private marina.
£73
includes taxes & fees
7 Sept - 8 Sept
Breezy Palms Resort
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.

3. 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.
£205
includes taxes & fees
9 Sept - 10 Sept
Pines & Palms Resort
A balcony with two white cups on saucers, overlooking a beach with palm trees and the ocean.
A view from a window overlooking a beach with palm trees and a wooden pier.

4. 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.
£146
includes taxes & fees
28 Sept - 29 Sept
Casa Morada
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.
£85
includes taxes & fees
16 Sept - 17 Sept
Drift Hotel
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.

6. 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.
£105
includes taxes & fees
10 Sept - 11 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
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.

7. 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.
£91
includes taxes & fees
27 Sept - 28 Sept
Rock Reef Resort
Four white Adirondack chairs facing a body of water with a clear sky.
A wooden deck with two chairs and a table, overlooking a beach with palm trees and boats.
A bedroom with a bed, a television, a dresser, and a door.
A bathroom with a sink, mirror, toilet, shower, and a window.

8. Coconut Palm Inn

Coconut Palm Inn
Tavernier
  • Escape to a private white sand paradise with paddleboarding, kayaking, and breathtaking sunsets on the waterfront.
£186
includes taxes & fees
15 Sept - 16 Sept
Coconut Palm Inn
A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.
A beach with lounge chairs, palm trees, and a view of the water.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A compact living space with a balcony, a television, and a dining area.

9. Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
  • Unwind on a private white sand beach with kayaking and sunset views at this waterfront paradise
£127
includes taxes & fees
28 Sept - 29 Sept
Atlantic Bay Resort
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A wooden pier leading to a thatched-roof structure with chairs and a table, overlooking the sea.
A marina with boats docked, a building with a blue roof, and a clear view of the water.
A balcony with a view of the sea, a white chair, and two buckets with a red shovel.

10. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
  • Discover tropical bliss at this Key Largo beach retreat, where private shorelines meet ocean adventures and poolside relaxation.
£116
includes taxes & fees
5 Oct - 6 Oct
Ocean Pointe Suites at Key Largo
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"The room was beautiful, clean and well maintained. Any issues were corrected immediately. Staff was always responsive and helpful. The only issue was: At this time of the year there is an issue with the smell coming from decaying seaweed in the bay which creates an odor in the beach and pool area. The odor subsided after the 3rd day. Otherwise, we had a wonderful vacation. TG"
Thomas 4-night trip
Posted less than an hour ago
Cheeca Lodge & Spa
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Spectacular and quiet place"
Yanet 2-night trip
Posted 1 hour ago
La Siesta Resort & Villas
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"Front desk, grounds crew, housekeeping and bartender are all friendly and helpful. Front desk team and bartender were attentive to our requests. Grounds crew was always busy keeping the property maintained and looking good. They even kept the beach cleaned up from seaweed and debris. The location is great with many good restaurants within a few miles and a couple within easy walking distance. This is our "go to" place in the Keys. Our many stays have always been great and we hate to leave."
Dan 3-night trip
Posted 1 hour ago
Pines & Palms Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Beautiful views and friendly staff. Lots of activities available at no charge. Will definitely be back!"
Jennifer 1-night trip
Posted 10 hours ago
Lime Tree Bay Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Clean, spacious suite with great marina-view balcony and full kitchen. Perfect location next door to dive shop. Waterside is Key Largo's best kept secret!"
Eleftheria 5-night trip
Posted 23 hours ago
Waterside Suites & Marina
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"I’ve been vacationing in Breezy Palms for years. It reminds me of old time Florida with beautiful sunsets and tranquility Even the rooster seemed tranquil at 4:15 AM. It’s my go to place when headed to the Keys."
Tammy 5-night trip
Posted 1 day ago
Breezy Palms Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Baseboard were removed off the wall. Did not gave it a clean look . Walls in the hallway slightly dirty."
Yuliet 1-night trip
Posted 2 days ago
Amara Cay Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Perfection!"
Lauren 3-night trip
Posted 3 days ago
Playa Largo Resort & Spa, Autograph Collection

Explore a world of travel with Expedia