Book Hotels in Upper Matecumbe Key, FL
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Top Upper Matecumbe Key hotels
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Sep 1 to Sep 2
$329 total
Sep 1 - Sep 2
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 ...
"Excellent treatment by the entire staff across the property"
Reviewed on Jul 31, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from Aug 18 to Aug 19
$234 total
Aug 18 - Aug 19
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. ...
"⭐⭐⭐⭐⭐ I had a wonderful stay at this hotel. The staff was welcoming, professional, and always ready to help with a smile. My room was spotless, comfortable, and well maintained, making it easy to relax after a long day. The hotel’s location was convenient, with great restaurants and attractions nearby. ..."
Reviewed on Aug 1, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $221 total per night from Aug 3 to Aug 4
$221 total
Aug 3 - Aug 4
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 ...
"I was somewhat disappointed. This place is no resort. It's a redone roadside motel in a pretty spot. We did like the pool and the water views, but the property wasn't really kept clean. The breakfast was weird and not very good. The guy making pancakes squished them onto the griddle so any fluffiness ..."
Reviewed on Jul 31, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $248 total per night from Aug 9 to Aug 10
$248 total
Aug 9 - Aug 10
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 ...
"Excellent Service"
Reviewed on Aug 1, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from Aug 9 to Aug 10
$266 total
Aug 9 - Aug 10
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, ...
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $143 total per night from Aug 4 to Aug 5
$143 total
Aug 4 - Aug 5
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.
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $167 total per night from Aug 2 to Aug 3
$167 total
Aug 2 - Aug 3
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 ...
Pines & Palms Resort
80401 Old Hwy Islamorada FL
$268 nightly
The price is $302 total per night from Aug 30 to Aug 31
$302 total
Aug 30 - Aug 31
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 ...
La Jolla Resort
82216 Overseas Highway Islamorada FL
$164 nightly
The price is $185 total per night from Aug 5 to Aug 6
$185 total
Aug 5 - Aug 6
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 ...
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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
1 properties
Recent Upper Matecumbe Key hotel reviews by fellow wanderers
Amara Cay Resort
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Excellent Service"
A verified traveler stayed at Amara Cay Resort
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