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Top Upper Matecumbe Key hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $421 total per night from Apr 12 to Apr 13
$421 total
per night
Apr 12 - Apr 13
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on Mar 12, 2026

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $308 total per night from Apr 14 to Apr 15
$308 total
per night
Apr 14 - Apr 15
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
We upgraded to an Ocean View and it was fantastic! Nice quiet vacation and great location with walkable restaurants and bars. Breakfast was special with awesome omlets by Chris!!

Reviewed on Mar 13, 2026

Opens in a new windowChesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $470 total per night from Apr 12 to Apr 13
$470 total
per night
Apr 12 - Apr 13
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
We had a beautiful time during our stay. The rooms are so comfortable and have beautiful views. The staff was kind and even checked on us to see if we needed more coffee. The views were perfect day and night. We enjoyed the pool and played some golf and relaxed. Best week ever!

Reviewed on Mar 14, 2026

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $265 total per night from Apr 7 to Apr 8
$265 total
per night
Apr 7 - Apr 8
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage ...
It was adequate and clean, nice desk person.

Reviewed on Mar 14, 2026

Opens in a new windowSunset Inn
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
The price is $308 total per night from Apr 5 to Apr 6
$308 total
per night
Apr 5 - Apr 6
A private beach and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are ...
The property was clean and inviting. We stayed in the room above the office. It was very quiet, clean and smelled fresh. The staff was excellent; he answered our questions and was very helpful when approached. Would happily stay here again!

Reviewed on Mar 11, 2026

Opens in a new windowLa Jolla Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $339 total per night from Mar 26 to Mar 27
$339 total
per night
Mar 26 - Mar 27
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
Desk staff was OK. Bar and restaurant staff seemed slow and overwhelmed even with a small crowd. Cleaning staff wandered around slowly looking at their phones.

Reviewed on Mar 14, 2026

Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $326 total per night from Mar 22 to Mar 23
$326 total
per night
Mar 22 - Mar 23
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...
Great place

Reviewed on Mar 6, 2026

Opens in a new windowLa Siesta Resort & Villas
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $284 total per night from Mar 24 to Mar 25
$284 total
per night
Mar 24 - Mar 25
A marina and an outdoor pool are featured at this aparthotel. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
Beautiful room! Newly renovated beautiful view clean great amenities! I was not sure what to expect and was very pleased. Highly recommend. Will stay here again

Reviewed on Mar 13, 2026

Opens in a new windowBreezy Palms Resort
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $265 total per night from Apr 12 to Apr 13
$265 total
per night
Apr 12 - Apr 13
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate ...
We were suppose to have pool villa. No view of the pool from our room. Did get $100 off our stay. Pool was dirty. Continental breakfast was good. Need railings in room for stairs. Need table lamp in living room. Shared balcony. Was woken up by loud music on balcony at 11 pm one night.

Reviewed on Mar 13, 2026

Opens in a new windowHadley Resort and Marina
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Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Amara Cay Resort

Amara Cay Resort

3 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Desk staff was OK. Bar and restaurant staff seemed slow and overwhelmed even with a small crowd. Cleaning staff wandered around slowly looking at their phones. "
A verified traveler stayed at Amara Cay Resort
Amara Cay Resort

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