Book Hotels in Upper Matecumbe Key, FL

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Top Upper Matecumbe Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $267 total per night from Jan 6 to Jan 7
$267 total
Jan 6 - Jan 7, 2026
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 ...
It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :)

Reviewed on Dec 23, 2025

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
$328 nightly
The price is $370 total per night from Jan 4 to Jan 5
$370 total
Jan 4 - Jan 5, 2026
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. ...
Fabulous waterfront, activities, and dining as well as the staff.

Reviewed on Dec 21, 2025

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
$308 nightly
The price is $347 total per night from Jan 4 to Jan 5
$347 total
Jan 4 - Jan 5, 2026
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 ...
Rooms at villas are a little small but loved staying there. The rooms at the main resort are spacious and the property is amazing.

Reviewed on Dec 25, 2025

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
$171 nightly
The price is $192 total per night from Jan 13 to Jan 14
$192 total
Jan 13 - Jan 14, 2026
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 ...
Staff was all kind! All furniture was a old, pealing back, or rusty. They bikes they advertised(which is why we booked there) were all broken :(

Reviewed on Dec 13, 2025

Opens in a new windowSunset Inn
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$143 nightly
The price is $161 total per night from Jan 7 to Jan 8
$161 total
Jan 7 - Jan 8, 2026
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 ...
Very clean. Newly renovated.

Reviewed on Dec 18, 2025

Opens in a new windowLa Jolla Resort
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night from Jan 4 to Jan 5
$347 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool ...
Great room great place. Very clean easy to get to wonderful staff

Reviewed on Dec 20, 2025

Opens in a new windowPines & Palms Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $305 total per night from Jan 5 to Jan 6
$305 total
Jan 5 - Jan 6, 2026
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 ...
Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special!

Reviewed on Dec 21, 2025

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
$242 nightly
The price is $273 total per night from Jan 6 to Jan 7
$273 total
Jan 6 - Jan 7, 2026
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 accommodations, very peaceful setting

Reviewed on Dec 25, 2025

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
$178 nightly
The price is $200 total per night from Jan 11 to Jan 12
$200 total
Jan 11 - Jan 12, 2026
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 ...
Comfortable stay. Great location.

Reviewed on Dec 8, 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 1 day ago
Travelocity Verified Review
"Rooms at villas are a little small but loved staying there. The rooms at the main resort are spacious and the property is amazing. "
A verified traveler stayed at Islander Resort
Islander Resort

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