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Top Upper Matecumbe Key hotels

Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$252 nightly
The price is $284 total per night from Apr 7 to Apr 8
$284 total
Apr 7 - Apr 8
Total with taxes and fees
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 ...
Yes pool was great! Very clean nice rooms, close to walk to a lot of fun things! Loved the bikes you can use

Reviewed on Mar 11, 2026

Opens in a new windowSunset Inn
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
$447 nightly
The price is $503 total per night from Mar 12 to Mar 13
$503 total
Mar 12 - Mar 13
Total with taxes and fees
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. ...
All 3 pools were excellent. The sandy beach looking over the Atlantic Ocean was amazing and relaxing at the same time. The ladies went to the spa the men played the par 3 course, which is included in the resort fee.

Reviewed on Mar 11, 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
$354 nightly
The price is $399 total per night from Mar 22 to Mar 23
$399 total
Mar 22 - Mar 23
Total with taxes and fees
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 ...
The ocean was visible from our room and the balcony was wonderful!

Reviewed on Mar 11, 2026

Opens in a new windowChesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$461 nightly
The price is $519 total per night from Mar 25 to Mar 26
$519 total
Mar 25 - Mar 26
Total with taxes and fees
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 ...
Absolutely loved this place. A little gem we found as we were driving. Decided to come in and take a look and booked straight away for a few days. Will be returning next year

Reviewed on Mar 11, 2026

Opens in a new windowIslander Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$274 nightly
The price is $308 total per night from Mar 12 to Mar 13
$308 total
Mar 12 - Mar 13
Total with taxes and fees
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
$302 nightly
The price is $340 total per night from Mar 22 to Mar 23
$340 total
Mar 22 - Mar 23
Total with taxes and fees
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 ...
My only complaint is the room and bathroom was not light enough. Otherwise, great place to stay! Walkable and bike-rideable to restaurants.

Reviewed on Mar 11, 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
$384 nightly
The price is $433 total per night from Mar 24 to Mar 25
$433 total
Mar 24 - Mar 25
Total with taxes and fees
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
$261 nightly
The price is $294 total per night from Mar 24 to Mar 25
$294 total
Mar 24 - Mar 25
Total with taxes and fees
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 . Paradise.

Reviewed on Mar 11, 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
$307 nightly
The price is $346 total per night from Mar 19 to Mar 20
$346 total
Mar 19 - Mar 20
Total with taxes and fees
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 ...
The view was perfect, the room was clean and comfortable. Staff was very friendly.

Reviewed on Mar 4, 2026

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

La Jolla Resort

La Jolla Resort

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"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! "
A verified traveler stayed at La Jolla Resort
La Jolla Resort

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