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
$241 nightly
The price is $271 total per night from Sep 27 to Sep 28
$271 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 ...
"Great location. Very good CLEANING staff and FRONT DESK staff are excellent"
Reviewed on Sep 14, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $209 total per night from Sep 29 to Sep 30
$209 total
Sep 29 - Sep 30
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. ...
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."
Reviewed on Sep 14, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $215 total per night from Oct 12 to Oct 13
$215 total
Oct 12 - Oct 13
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 ...
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Reviewed on Sep 13, 2026
La Jolla Resort
82216 Overseas Highway Islamorada FL
$133 nightly
The price is $150 total per night from Sep 24 to Sep 25
$150 total
Sep 24 - Sep 25
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 ...
"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t ..."
Reviewed on Sep 12, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $230 total per night from Sep 20 to Sep 21
$230 total
Sep 20 - Sep 21
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 ...
"Beautiful lobby, nice outdoor area, room is clean, the elevator is a bit old though. Pool is very big, kids love it."
Reviewed on Sep 13, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from Sep 16 to Sep 17
$122 total
Sep 16 - Sep 17
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.
"Great place... it is not fancy but it is comfortable, spacious, pool is clean, well located.... I can come back anytime"
Reviewed on Sep 14, 2026
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
$186 nightly
The price is $209 total per night from Oct 7 to Oct 8
$209 total
Oct 7 - Oct 8
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
$156 nightly
The price is $175 total per night from Sep 16 to Sep 17
$175 total
Sep 16 - Sep 17
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
Breezy Palms Resort
5 out of 5
Posted 15 hours ago
Travelocity Verified Review
"Great place... it is not fancy but it is comfortable, spacious, pool is clean, well located.... I can come back anytime"
A verified traveler stayed at Breezy Palms Resort
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