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

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Check availability on Upper Matecumbe Key Beach Resorts & Hotels

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

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
£141
includes taxes & fees
13 Sept - 14 Sept
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, 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.
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.
£83
includes taxes & fees
13 Sept - 14 Sept
Breezy Palms Resort
A beach with palm trees, a wooden pier, and beach chairs.
A beachside resort with a pool area, lounge chairs, and palm trees.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

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.
£175
includes taxes & fees
10 Sept - 11 Sept
Pines & 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.
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.
£140
includes taxes & fees
7 Oct - 8 Oct
Casa Morada
A beach with lounge chairs, kayaks, and a wooden pier.
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.
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.
£79
includes taxes & fees
27 Sept - 28 Sept
Drift Hotel
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A covered outdoor area with a view of a beach and palm trees.
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.
£91
includes taxes & fees
27 Sept - 28 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.
£105
includes taxes & fees
15 Sept - 16 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A marina with boats docked, a building with a blue roof, and a clear view of the water.
A poolside area with a water feature, a palm tree, and lounge chairs.
A balcony with a view of the sea, a white chair, and two buckets with a red shovel.

8. 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.
£114
includes taxes & fees
15 Sept - 16 Sept
Ocean Pointe Suites at Key Largo
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 compact living space with a balcony, a television, and a dining area.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.

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 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.

10. 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.
£90
includes taxes & fees
20 Sept - 21 Sept
Seafarer 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

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Encantada"
Franklin 2-night trip
Posted 7 hours ago
La Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great"
Juan 2-night trip
Posted 12 hours ago
Hadley Resort and Marina
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Amazing !! 💯 recommend. Clean room, excellent location and ocean view. I love this place !!"
Gladys Jeannine 1-night trip
Posted 16 hours ago
Lime Tree Bay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"Amazing"
Leilanis 1-night trip
Posted 20 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
La Jolla Resort

La Jolla Resort

10/10 Excellent
"Great place, clean, quiet. Calm, relaxing, fun little beach, sunset views - super cool cat!"
Paul 1-night trip
Posted 21 hours ago
La Jolla Resort
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"We loved the place"
Badoglio Urbano 2-night trip
Posted 1 day ago
Hawks Cay Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"After multiple visits to Islamorada this is now our new place to stay whenever we visit. Great location, beautiful property and incredibly friendly staff!!"
Donald 2-night trip
Posted 2 days ago
Pines & Palms Resort
Islander Resort

Islander Resort

10/10 Excellent
"Everything is super great beside Beach If you looking to swim in the ocean not best pick"
Rostyslav 2-night trip
Posted 2 days ago
Islander Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Todo estaba limpio y cómodo..excelente para lugar"
Carlos 1-night trip
Posted 2 days ago
Waterside Suites & Marina

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