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
$261 nightly
The price is $293 total per night from Nov 15 to Nov 16
$293 total
Nov 15 - Nov 16
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 ...
"💜"
Reviewed on Oct 25, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$123 nightly
The price is $138 total per night from Nov 3 to Nov 4
$138 total
Nov 3 - Nov 4
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.
"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."
Reviewed on Oct 22, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $248 total per night from Nov 15 to Nov 16
$248 total
Nov 15 - Nov 16
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 ...
"Great property however the rooms could use an update."
Reviewed on Oct 25, 2026
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from Oct 27 to Oct 28
$178 total
Oct 27 - Oct 28
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 ...
"Can’t wait to stay again in the spring. Amazing property."
Reviewed on Oct 21, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$234 nightly
The price is $263 total per night from Nov 1 to Nov 2
$263 total
Nov 1 - Nov 2
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. ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $212 total per night from Nov 4 to Nov 5
$212 total
Nov 4 - Nov 5
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 ...
La Jolla Resort
82216 Overseas Highway Islamorada FL
$184 nightly
The price is $207 total per night from Oct 27 to Oct 28
$207 total
Oct 27 - Oct 28
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 ...
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $252 total per night from Nov 15 to Nov 16
$252 total
Nov 15 - Nov 16
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, ...
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 27 to Oct 28
$207 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
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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 12 hours ago
Travelocity Verified Review
"Great property however the rooms could use an update."
A verified traveler stayed at Amara Cay Resort
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