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Where to stay in Upper Matecumbe Key?
Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Upper Matecumbe Key on Hotels.com. These Upper Matecumbe Key hotels consistently deliver on quality, location and traveller experience. Last updated on 14 October 2026.
1. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
9.2 out of 10, Wonderful, (1,804 reviews)
"Beautiful property and great little breakfast!!"
Debrah
The price is AU$315
includes taxes & fees
18 Oct - 19 Oct
2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
9.2 out of 10, Wonderful, (1,477 reviews)
"Clean rooms, staff amazing, restaurant great location beautiful "
Kevin
The price is AU$406
includes taxes & fees
19 Oct - 20 Oct
3. Amara Cay Resort
Amara Cay ResortMatecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Good place to stay, very friendly staff and great breakfast!"
Christos
The price is AU$350
includes taxes & fees
18 Oct - 19 Oct
4. Islander Resort
Islander ResortMatecumbe
9.4 out of 10, Exceptional, (1,141 reviews)
"Great place with great amenities."
Wendy
The price is AU$440
includes taxes & fees
18 Oct - 19 Oct
5. La Jolla Resort
La Jolla ResortMatecumbe
9.2 out of 10, Wonderful, (1,009 reviews)
"Good location and great staff"
adrian
The price is AU$248
includes taxes & fees
15 Oct - 16 Oct
6. Breezy Palms Resort
Breezy Palms ResortMatecumbe
9.0 out of 10, Wonderful, (768 reviews)
"Rooms are nice and clean being Right on the water is a plus . Would visit again"
Greg
The price is AU$181
includes taxes & fees
18 Oct - 19 Oct
7. Hadley Resort and Marina
Hadley Resort and MarinaMatecumbe
7.6 out of 10, Good, (1,000 reviews)
"The ocean view was amazing"
Peggy
The price is AU$277
includes taxes & fees
12 Nov - 13 Nov
8. La Siesta Resort & Villas
La Siesta Resort & VillasMatecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Clean quiet and serene.
Staff was so helpful and kind!"
Cassandra
The price is AU$377
includes taxes & fees
8 Nov - 9 Nov
9. Pines & Palms Resort
Pines & Palms ResortMatecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Wonderful property and friendly staff. Rooms were lovely and beds very comfortable"
Jonathan
The price is AU$413
includes taxes & fees
15 Oct - 16 Oct
10. Casa Morada
Casa MoradaMatecumbe
9.4 out of 10, Exceptional, (463 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
Lois
The price is AU$269
includes taxes & fees
26 Oct - 27 Oct
11. Bayside Villas by Islander Resort
Bayside Villas by Islander ResortMatecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
beata
The price is AU$522
includes taxes & fees
20 Oct - 21 Oct
12. Sands of Islamorada
Sands of IslamoradaMatecumbe
8.8 out of 10, Excellent, (416 reviews)
"Such a nice little property - Room was so nice.. I would stay there again!"
Charlotte
The price is AU$325
includes taxes & fees
19 Oct - 20 Oct
13. The Islands of Islamorada
The Islands of IslamoradaMatecumbe
9.6 out of 10, Exceptional, (81 reviews)
"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
The price is AU$913
includes taxes & fees
20 Oct - 21 Oct
14. Drift Hotel
Drift HotelKey Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Wonderful place! Beautiful beach and the staff were awesome! "
Faith
The price is AU$174
includes taxes & fees
15 Oct - 16 Oct
15. Lime Tree Bay Resort
Lime Tree Bay ResortLong Key
9.4 out of 10, Exceptional, (1,539 reviews)
"The resort was very relaxing."
Deanna
The price is AU$252
includes taxes & fees
15 Oct - 16 Oct
16. Rock Reef Resort
Rock Reef ResortRock Harbor
9.2 out of 10, Wonderful, (1,186 reviews)
"Perfect for our night stop down to Key West.
Clean room and very friendly staff."
sharon
The price is AU$123
includes taxes & fees
27 Oct - 28 Oct
17. Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
7.8 out of 10, Good, (1,001 reviews)
"Good location and great room size, but the hotel is definitely needing upgrades."
Michael
The price is AU$219
includes taxes & fees
15 Oct - 16 Oct
18. Seafarer Key Largo
Seafarer Key LargoRock Harbor
9.2 out of 10, Wonderful, (255 reviews)
"Great stay, great staff, great room."
Jennifer
The price is AU$204
includes taxes & fees
25 Oct - 26 Oct
19. Hampton Inn Key Largo Manatee Bay
Hampton Inn Key Largo Manatee BayKey Largo
8.8 out of 10, Excellent, (1,108 reviews)
"Perfectly located near John Pennekamp State Park!"
Vi
The price is AU$187
includes taxes & fees
20 Oct - 21 Oct
20. Atlantic Bay Resort
Atlantic Bay ResortTavernier
9.4 out of 10, Exceptional, (828 reviews)
The price is AU$262
includes taxes & fees
20 Oct - 21 Oct
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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Showing deals for:14 Oct - 15 Oct
9.2 out of 10, Wonderful, (1,804 reviews)
AU$20 off
The price is AU$316
for 1 room
includes taxes & fees
Showing deals for:23 Oct - 25 Oct
9.2 out of 10, Wonderful, (1,804 reviews)
AU$119 off
The price is AU$1,231
for 2 nights, 1 room
AU$616 per night
includes taxes & fees
Check out pet-friendly hotels in Upper Matecumbe Key
9.2 out of 10, Wonderful, (1804)
The price is AU$315
includes taxes & fees
18 Oct - 19 Oct
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.
Go beyond your typical stay in Upper Matecumbe Key
Pet friendly
Pool
Top landmarks in Upper Matecumbe Key
Learn more about Upper Matecumbe Key
Upper Matecumbe Key is well known for its attractions such as Bud n' Mary's Dive Center and Florida Keys Brewing Co..
Top Upper Matecumbe Key Hotel Reviews
Casa Morada
Casa MoradaMatecumbe
10/10 Exceptional
We were greeted with a wonderful dazzling smile, an upgrade to a beachfront and a cocktail. At that point they had won us. This place is wonderful and ever so friendly resort. We had a wonderful yet too short a stay here on our way down to Key West. A sunset sail with Captain Bill is a must. My wife and I loved it.
Brett