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Our top choices for Upper Matecumbe Key hotels
1. Islander Resort
Islander ResortMatecumbe
9.4 out of 10, Exceptional, (1,162 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
DEBORAH
The price is CA $253
CA $388 total
includes taxes & fees
Nov 15 - Nov 16
2. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
9.4 out of 10, Exceptional, (1,810 reviews)
"Location is amazing make sure to book a balcony with a view"
Olga Vasiliy
The price is CA $203
CA $307 total
includes taxes & fees
Nov 10 - Nov 11
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
9.2 out of 10, Wonderful, (1,511 reviews)
"Great place. Phenomenal food!"
Brandon
The price is CA $256
CA $391 total
includes taxes & fees
Nov 19 - Nov 20
4. La Jolla Resort
La Jolla ResortMatecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
Jane
The price is CA $177
CA $239 total
includes taxes & fees
Nov 18 - Nov 19
5. Amara Cay Resort
Amara Cay ResortMatecumbe
8.8 out of 10, Excellent, (1,333 reviews)
"Great location as well."
Amir
The price is CA $235
CA $368 total
includes taxes & fees
Nov 15 - Nov 16
6. Breezy Palms Resort
Breezy Palms ResortMatecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
Gavin
The price is CA $102
CA $188 total
includes taxes & fees
Nov 29 - Nov 30
7. Hadley Resort and Marina
Hadley Resort and MarinaMatecumbe
7.6 out of 10, Good, (1,002 reviews)
"Can’t wait to stay again in the spring. Amazing property."
Jason
The price is CA $177
CA $245 total
includes taxes & fees
Nov 10 - Nov 11
8. Pines & Palms Resort
Pines & Palms ResortMatecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
Michael
The price is CA $270
CA $382 total
includes taxes & fees
Nov 15 - Nov 16
9. La Siesta Resort & Villas
La Siesta Resort & VillasMatecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
Brianne
The price is CA $218
CA $349 total
includes taxes & fees
Nov 15 - Nov 16
10. Bayside Villas by Islander Resort
Bayside Villas by Islander ResortMatecumbe
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!"
Brian
The price is CA $354
CA $501 total
includes taxes & fees
Nov 9 - Nov 10
11. Sands of Islamorada
Sands of IslamoradaMatecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
Nicolas
The price is CA $271
CA $324 total
includes taxes & fees
Nov 16 - Nov 17
12. The Islands of Islamorada
The Islands of IslamoradaMatecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining.
The property is pristine and gorgeous.
My only critique would be a lack of on property food options.
We will definitely be back."
Catherine
The price is CA $896
CA $1,111 total
includes taxes & fees
Nov 29 - Nov 30
13. Casa Morada
Casa MoradaMatecumbe
9.2 out of 10, Wonderful, (467 reviews)
"Very helpful staff and great location"
David
The price is CA $259
CA $308 total
includes taxes & fees
Nov 16 - Nov 17
14. Lime Tree Bay Resort
Lime Tree Bay ResortLong Key
9.4 out of 10, Exceptional, (1,585 reviews)
"We truly enjoyed our stay at Lime Tree Bay. The room was nice and clean and I loved being able to relax in the chairs/hammocks close to the water."
Jessica
The price is CA $175
CA $260 total
includes taxes & fees
Nov 17 - Nov 18
15. Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
7.8 out of 10, Good, (1,003 reviews)
"The view, the property amenities and room are great! Had a great time!"
ruben
The price is CA $139
CA $201 total
includes taxes & fees
Nov 17 - Nov 18
16. Drift Hotel
Drift HotelKey Largo
9.0 out of 10, Wonderful, (1,003 reviews)
"Excellent location"
kelly
The price is CA $147
CA $182 total
includes taxes & fees
Nov 9 - Nov 10
17. Rock Reef Resort
Rock Reef ResortRock Harbor
9.2 out of 10, Wonderful, (1,206 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
keith
The price is CA $128
CA $144 total
includes taxes & fees
Nov 15 - Nov 16
18. Atlantic Bay Resort
Atlantic Bay ResortTavernier
9.4 out of 10, Exceptional, (836 reviews)
"Excellent Stay!"
Annette
The price is CA $211
CA $269 total
includes taxes & fees
Dec 1 - Dec 2
19. Fisher Inn Resort & Marina
Fisher Inn Resort & MarinaIslamorada
8.2 out of 10, Very good, (1,002 reviews)
"We enjoyed everything!"
Susan
The price is CA $182
CA $251 total
includes taxes & fees
Nov 29 - Nov 30
20. Creekside Inn
Creekside InnTavernier
7.8 out of 10, Good, (1,021 reviews)
"Quite and relaxing place"
MARIO
The price is CA $174
CA $196 total
includes taxes & fees
Dec 8 - Dec 9
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.
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Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..
Top Upper Matecumbe Key Hotel Reviews
The Islands of Islamorada
The Islands of IslamoradaMatecumbe
10/10 Excellent
Phenomenal hotel, Marcel and Jackie were amazing with the kids and the activities offered.
This is the first hotel where I feel there is great value in the resort fee with all that's included.
Kenneth
