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
$316 nightly
The price is $356 total per night from Jun 21 to Jun 22
$356 total
Jun 21 - Jun 22
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 rooms were very clean and the staff were all very nice! We would 100% come back and stay at this resort! 10/10"
Reviewed on Jun 12, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $299 total per night from Jun 15 to Jun 16
$299 total
Jun 15 - Jun 16
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. ...
"Great experience as always!"
Reviewed on Jun 13, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $258 total per night from Jun 14 to Jun 15
$258 total
Jun 14 - Jun 15
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 ...
"Everyone was friendly and room was nice."
Reviewed on Jun 13, 2026
Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $343 total per night from Jun 24 to Jun 25
$343 total
Jun 24 - Jun 25
Total with taxes and fees
This hotel features 3 restaurants, a bar/lounge, and an outdoor pool. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free ...
"What an amazing stay! From the moment we entered the property the staff was happy, friendly and welcoming. DJ Nick the shuttle driver was so much fun and efficient- ask him to do his duck voice. The daily activities around the property were so much fun for our little one- the fresh fruit they brought ..."
Reviewed on Jun 12, 2026
La Jolla Resort
82216 Overseas Highway Islamorada FL
$214 nightly
The price is $241 total per night from Jun 21 to Jun 22
$241 total
Jun 21 - Jun 22
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 location was beautiful, right on the water. Lots to do on and around the property."
Reviewed on Jun 12, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$253 nightly
The price is $285 total per night from Jul 7 to Jul 8
$285 total
Jul 7 - Jul 8
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 ...
"I have mixed reviews. The staff was very helpful, especially the lobby bartender, Marcus. The grounds and the pool area are very nicely maintained. The location is very close to Bud and Mary's marina, where my husband booked a half day fishing charter. Also, very close to the Midway Cafe- excellent ..."
Reviewed on Jun 13, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $271 total per night from Jul 6 to Jul 7
$271 total
Jul 6 - Jul 7
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, ...
"Loved staying here. Had a 2 bedroom suite for 8 (4 adults, 4 kids) and it was perfect. Great amenities, sights, right where you wanna be."
Reviewed on Jun 11, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $196 total per night from Jun 23 to Jun 24
$196 total
Jun 23 - Jun 24
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.
"Excellent"
Reviewed on Jun 12, 2026
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jun 17 to Jun 18
$197 total
Jun 17 - Jun 18
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 location was great. Walkable to places. It was overall quiet and the small beach area was nice. The pool could have been cleaner and having to get towels from the front desk was not convenient. Also having no bathroom by the pool was also not convenient. Overall, it was nice and I would stay ..."
Reviewed on Jun 11, 2026
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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
2 properties
Recent Upper Matecumbe Key hotel reviews by fellow wanderers
Cheeca Lodge & Spa
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Great experience as always!"
A verified traveler stayed at Cheeca Lodge & Spa
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