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

Search Condo 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 prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,458 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is Rp2.667.547
Rp4.310.237 total
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,785 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is Rp2.704.248
Rp4.049.322 total
includes taxes & fees
28 Sept - 29 Sept
Chesapeake Beach Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the amenities"
United States
Kayla
The price is Rp1.732.115
Rp2.452.241 total
includes taxes & fees
28 Sept - 29 Sept
La Jolla 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, (754 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
The price is Rp1.463.570
Rp1.932.271 total
includes taxes & fees
29 Sept - 30 Sept
Breezy Palms Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

5. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,127 reviews)
"Great palace to stay at a reasonable price"
United States
John
The price is Rp5.123.839
Rp7.073.386 total
includes taxes & fees
27 Oct - 28 Oct
Islander Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

6. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 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 Rp3.528.681
Rp4.956.758 total
includes taxes & fees
1 Oct - 2 Oct
Pines & Palms 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.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"amazing clean stay."
United States
MICHAEL
The price is Rp2.767.356
Rp4.422.521 total
includes taxes & fees
29 Sept - 30 Sept
Amara Cay Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

8. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,003 reviews)
"Great place"
United States
weder
The price is Rp2.115.239
Rp2.963.819 total
includes taxes & fees
28 Sept - 29 Sept
Hadley Resort and Marina
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

9. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (80 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 Rp7.411.842
Rp9.473.461 total
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (464 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is Rp4.672.683
Rp6.565.835 total
includes taxes & fees
28 Sept - 29 Sept
Bayside Villas by Islander Resort
A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

11. 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 Rp3.437.376
Rp4.108.739 total
includes taxes & fees
1 Oct - 2 Oct
Sands of Islamorada

12. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (460 reviews)
"Very helpful staff and great location"
United States
David
The price is Rp2.839.953
Rp3.396.378 total
includes taxes & fees
6 Oct - 7 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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Loved the kayak, and breakfast and the view! Everything!"
Sebastian 1-night trip
Posted 13 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
5,123
Accommodation
0 Condo Resorts
Lowest Price
Rp1.932.271
Highest Price
Rp9.473.461