Book Hotels in Upper Matecumbe Key, FL
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Top Upper Matecumbe Key hotels
The Islands of Islamorada
82779 Old Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$599 nightly
The price is $674 total per night from Aug 13 to Aug 14
$674 total
Aug 13 - Aug 14
Total includes taxes and fees
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 property!"
Reviewed on Aug 4, 2025
Sunset Inn
82200 Overseas Hwy, Islamorada, FL
$134 nightly
The price is $151 total per night from Aug 25 to Aug 26
$151 total
Aug 25 - Aug 26
Total includes 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 ...
"Comfortable"
Reviewed on Jul 25, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $214 total per night from Aug 17 to Aug 18
$214 total
Aug 17 - Aug 18
Total includes 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 ...
"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"
Reviewed on Aug 11, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $236 total per night from Aug 14 to Aug 15
$236 total
Aug 14 - Aug 15
Total includes 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. ...
"Great all around!"
Reviewed on Aug 8, 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $293 total per night from Aug 20 to Aug 21
$293 total
Aug 20 - Aug 21
Total includes 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 ...
"Amazing resort."
Reviewed on Aug 8, 2025
La Jolla Resort
82216 Overseas Highway, Islamorada, FL
$125 nightly
The price is $141 total per night from Aug 26 to Aug 27
$141 total
Aug 26 - Aug 27
Total includes 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 ...
"We enjoyed the pool. We also used resort provided kayaks in the open water. It was very relaxing. We only stayed one day as we were traveling south."
Reviewed on Aug 9, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $276 total per night from Sep 1 to Sep 2
$276 total
Sep 1 - Sep 2
Total includes 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 ...
"The staff was very personable and accommodating.. it was our 32nd weeding anniversary and they had left a handwritten note and a treat in our room… it was appreciated… The grounds were nice and clean with the exception of the water area around the end of the property where the event area is located ..."
Reviewed on Aug 11, 2025
La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $222 total per night from Sep 8 to Sep 9
$222 total
Sep 8 - Sep 9
Total includes 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, ...
"My family had a great stay at La Siesta Resort! The staff was very kind and welcoming; they had everything ready ahead of our stay and even provided us with a free upgrade on the accommodation to boot! The pool and beach/marina area are great spaces and there were beach chairs and umbrellas throughout. ..."
Reviewed on Aug 10, 2025
Hadley Resort and Marina
82749 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $172 total per night from Aug 17 to Aug 18
$172 total
Aug 17 - Aug 18
Total includes 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 ...
Gem in Islamorada
"I love this place, it’s chill, dog friendly, ramp and docks for ease of throwing in my paddleboard. Insanely beautiful views, and central to everything."
Reviewed on Jul 17, 2025
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See all available properties in Upper Matecumbe Key
View all propertiesLowest 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.
Hotels in Upper Matecumbe Key with star-rating
Check Upper Matecumbe Key Hotels by Star Rating
5 Star Hotels
3 properties
Recent Upper Matecumbe Key hotel reviews by fellow wanderers
Chesapeake Beach Resort
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"
A verified traveler stayed at Chesapeake Beach Resort
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An Attraction
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