Book Hotels in Upper Matecumbe Key, FL

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Top Upper Matecumbe Key hotels

Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$236 nightly
The price is $265 total per night from Apr 7 to Apr 8
$265 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
$371 nightly
The price is $418 total per night from Apr 12 to Apr 13
$418 total
Apr 12 - Apr 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. ...
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
$290 nightly
The price is $327 total per night from Apr 12 to Apr 13
$327 total
Apr 12 - Apr 13
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 ...
Nice place. Room and grounds were spotless

Reviewed on Mar 12, 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
$372 nightly
The price is $419 total per night from Apr 12 to Apr 13
$419 total
Apr 12 - Apr 13
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
$324 nightly
The price is $365 total per night from Mar 16 to Mar 17
$365 total
Mar 16 - Mar 17
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
$301 nightly
The price is $339 total per night from Mar 26 to Mar 27
$339 total
Mar 26 - Mar 27
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 ...
yes spotless

Reviewed on Mar 12, 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
$322 nightly
The price is $363 total per night from Mar 22 to Mar 23
$363 total
Mar 22 - Mar 23
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
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $289 total per night from Apr 12 to Apr 13
$289 total
Apr 12 - Apr 13
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
$235 nightly
The price is $265 total per night from Apr 12 to Apr 13
$265 total
Apr 12 - Apr 13
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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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.

Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Cheeca Lodge & Spa

Cheeca Lodge & Spa

3 out of 5
Posted 4 hours ago
Travelocity Verified Review
"We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window"
A verified traveler stayed at Cheeca Lodge & Spa
Cheeca Lodge & Spa

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