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
$312 nightly
The price is $351 total per night from Aug 10 to Aug 11
$351 total
Aug 10 - Aug 11
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 ...
"We love The Islander. We enjoyed our stay and can't wait to spend more time at this property."
Reviewed on Jul 31, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Aug 11 to Aug 12
$232 total
Aug 11 - Aug 12
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 ...
"Great experience!"
Reviewed on Jul 31, 2026
Sunset Inn
82200 Overseas Hwy Islamorada FL
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also ...
"Great location. The shower is odd (no door just an opening beyond the extended glass), turning on the water can be chilling at first LOL."
Reviewed on Jul 24, 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 ...
"The property was beautiful"
Reviewed on Jul 30, 2026
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 2 to Aug 3
$143 total
Aug 2 - Aug 3
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.
"I was pleasantly surprised at how nice everything was. We were just needing a place to sleep for a road trip so as long as it was clean and fairly comfortable we were fine but this place exceeded my expectations. It’s an older motel but obviously remodeled and well appointed. It has a kitchenette ..."
Reviewed on Jul 31, 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, ...
"Great place to stay!"
Reviewed on Jul 31, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $233 total per night from Aug 10 to Aug 11
$233 total
Aug 10 - Aug 11
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. ...
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 ...
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 ...
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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
Chesapeake Beach Resort
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Great experience!"
A verified traveler stayed at Chesapeake Beach Resort
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