Book Hotels in Upper Matecumbe Key, FL

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Top Upper Matecumbe Key hotels

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
The price is $740 total per night from Jan 19 to Jan 20
$740 total
per night
Jan 19 - Jan 20
2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on Nov 25, 2025

Opens in a new windowThe Islands of Islamorada
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 $280 total per night from Jan 28 to Jan 29
$280 total
per night
Jan 28 - Jan 29
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 ...
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good

Reviewed on Jan 11, 2026

Opens in a new windowChesapeake Beach Resort
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 $361 total per night from Jan 29 to Jan 30
$361 total
per night
Jan 29 - Jan 30
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. ...
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.

Reviewed on Jan 8, 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $428 total per night from Jan 29 to Jan 30
$428 total
per night
Jan 29 - Jan 30
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 ...
Really liked this place! Had a few issues with hot water and the shower. They were definitely responsive about fixing but there were some language barriers which made that a little difficult. Some of the furniture around the pool needed some love. And there was a lot of empty space on the property ...

Reviewed on Jan 13, 2026

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
The price is $223 total per night from Jan 25 to Jan 26
$223 total
per night
Jan 25 - Jan 26
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 ...
Checkin was easy, pool was wonderful. Staff was very helpful when needed. Room was exactly what we needed and very clean! Only tiny complaint would be that the doors stick a bit and had to always double check that they latched!

Reviewed on Jan 6, 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 $212 total per night from Jan 19 to Jan 20
$212 total
per night
Jan 19 - Jan 20
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 ...
It was very nice

Reviewed on Jan 7, 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 $308 total per night from Jan 27 to Jan 28
$308 total
per night
Jan 27 - Jan 28
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 ...
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on Jan 10, 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 $403 total per night from Jan 25 to Jan 26
$403 total
per night
Jan 25 - Jan 26
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, ...
The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 12, 2026

Opens in a new windowLa Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Fully refundable
The price is $200 total per night from Jan 19 to Jan 20
$200 total
per night
Jan 19 - Jan 20
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 ...
Enjoy here and quiet place

Reviewed on Dec 27, 2025

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

Islander Resort

Islander Resort

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Rooms are clean, staff is friendly and the place is beautifull"
A verified traveler stayed at Islander Resort
Islander Resort

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