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
$247 nightly
The price is $278 total per night from Sep 27 to Sep 28
$278 total
Sep 27 - Sep 28
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 ...
"The property was well maintained and clean. All staff were friendly and helpful. Amenities were nice. Very relaxing atmosphere"
Reviewed on Sep 19, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $221 total per night from Oct 1 to Oct 2
$221 total
Oct 1 - Oct 2
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 pool, great breakfast with seating outside with nice views"
Reviewed on Sep 19, 2026
La Jolla Resort
82216 Overseas Highway Islamorada FL
$135 nightly
The price is $151 total per night from Sep 22 to Sep 23
$151 total
Sep 22 - Sep 23
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 room was very nice and neat !"
Reviewed on Sep 19, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Sep 21 to Sep 22
$232 total
Sep 21 - Sep 22
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. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $245 total per night from Sep 27 to Sep 28
$245 total
Sep 27 - Sep 28
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 ...
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Sep 30 to Oct 1
$110 total
Sep 30 - Oct 1
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.
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
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, ...
Casa Morada
82200 overseas HWY Islamorada FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Oct 19 to Oct 20
$207 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $166 total per night from Sep 28 to Sep 29
$166 total
Sep 28 - Sep 29
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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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
Islander Resort
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The property was well maintained and clean. All staff were friendly and helpful. Amenities were nice. Very relaxing atmosphere"
A verified traveler stayed at Islander Resort
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