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

Search Inns 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 prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,804 reviews)
"Great place"
United States
Phelicia
The price is 3.917.029 ₫
5.865.332 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,141 reviews)
"Amazing place would definitely recommend"
United States
Steven
The price is 5.393.856 ₫
7.964.235 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Islander Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

3. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Super clean resort."
United States
Danielle
The price is 4.008.439 ₫
6.405.901 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Amara Cay Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

4. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (768 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is 2.543.929 ₫
3.275.730 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Breezy Palms Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

5. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,477 reviews)
The price is 5.160.468 ₫
7.701.934 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Cheeca Lodge & Spa
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

6. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice hotel."
United States
Brett
The price is 3.342.116 ₫
4.489.348 ₫ total
includes taxes & fees
15 Oct - 16 Oct
La Jolla Resort
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

7. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Great place"
United States
weder
The price is 3.710.869 ₫
5.020.890 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Hadley Resort and Marina
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

8. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is 4.358.521 ₫
6.799.743 ₫ total
includes taxes & fees
1 Nov - 2 Nov
La Siesta Resort & Villas
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

9. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
The price is 5.344.585 ₫
7.442.289 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Pines & Palms Resort
A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

10. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
United States
Nicolas
The price is 4.901.148 ₫
5.864.003 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Sands of Islamorada
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

11. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (81 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is 13.528.152 ₫
16.918.353 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Islands of Islamorada
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

12. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is 6.717.427 ₫
9.452.084 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Bayside Villas by Islander Resort
Exterior

13. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (463 reviews)
"Very helpful staff and great location"
United States
David
The price is 4.058.446 ₫
4.857.436 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Casa Morada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Beautiful"
Wesley 2-night trip
Posted 2 hours ago
Amara Cay Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Inns information

Number of reviews
5,509
Accommodation
0 Inns
Lowest Price
3.275.730 ₫
Highest Price
16.918.353 ₫