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

Beach Resorts in Upper Matecumbe Key

  • 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 Resorts

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
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
S$276
includes taxes & fees
13 Oct - 14 Oct
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.
A bathroom with a marble floor, a wooden vanity, a toilet, and a shower curtain.
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 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.
S$138
includes taxes & fees
4 Oct - 5 Oct
Breezy Palms Resort
Exterior
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.
View from property

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.
S$242
includes taxes & fees
7 Oct - 8 Oct
Casa Morada
A beach with palm trees, a wooden pier, and beach chairs.
A beachside resort with a pool area, lounge chairs, and palm trees.
Room
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

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.
S$367
includes taxes & fees
15 Oct - 16 Oct
Pines & Palms Resort
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 pool area with a view of the ocean, surrounded by palm trees and a clear sky.

5. 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.
S$145
includes taxes & fees
4 Oct - 5 Oct
Rock Reef 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 tree with string lights, a wooden bench, and a building in the background.

6. 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.
S$148
includes taxes & fees
26 Oct - 27 Oct
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 modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.
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.
S$182
includes taxes & fees
8 Oct - 9 Oct
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 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 beachside lounge with two blue umbrellas, a hammock, and lounge chairs.
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.
S$150
includes taxes & fees
4 Oct - 5 Oct
Seafarer Key Largo
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
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.
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

9. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
S$267
includes taxes & fees
8 Oct - 9 Oct
Kona Kai Resort and Gallery - Adults Only
A marina with boats docked along a waterfront, surrounded by buildings and palm trees.
A balcony with a view of the sea, a table, and two chairs.
A marina with boats docked along a waterfront, surrounded by buildings and palm trees.
A balcony with wicker furniture and a glass table, overlooking a marina with boats and palm trees.

10. Waterside Suites & Marina

Waterside Suites & Marina
Key Largo
S$195
includes taxes & fees
4 Oct - 5 Oct
Waterside Suites & Marina
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We really enjoyed our stay except for rain"
Lee 2-night trip
Posted 9 hours ago
Chesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"We have a pleasant stay."
gladys 1-night trip
Posted 11 hours ago
Lime Tree Bay Resort
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"So serene and peaceful Love this place!!"
Kathleen 2-night trip
Posted 16 hours ago
The Pelican Key Largo Cottages
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Always my to go place in the Keys! Very friendly staff. Clean rooms."
Lisandra 2-night trip
Posted 1 day ago
Bayside Inn Key Largo
Islander Resort

Islander Resort

10/10 Excellent
"It great amenities but pools are small."
Jaily 2-night trip
Posted 2 days ago
Islander Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"First time staying and we enjoyed it"
Pamela 1-night trip
Posted 3 days ago
Hadley Resort and Marina
Amara Cay Resort

Amara Cay Resort

8/10 Good
"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"
Melissa 1-night trip
Posted 4 days ago
Amara Cay Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 7 days ago
Casa Morada

Explore a world of travel with Expedia