Book Hotels in Upper Matecumbe Key, FL
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Top Upper Matecumbe Key hotels
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 Oct 18 to Oct 19
$212 total
Oct 18 - Oct 19
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 location"
Reviewed on Oct 16, 2026
La Jolla Resort
82216 Overseas Highway Islamorada FL
$155 nightly
The price is $174 total per night from Oct 18 to Oct 19
$174 total
Oct 18 - Oct 19
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 ...
"It was quaint and right on the water"
Reviewed on Oct 13, 2026
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $212 total per night from Nov 9 to Nov 10
$212 total
Nov 9 - Nov 10
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 ...
"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was ..."
Reviewed on Oct 15, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $261 total per night from Oct 19 to Oct 20
$261 total
Oct 19 - Oct 20
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. ...
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Nov 15 to Nov 16
$329 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 ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Oct 18 to Oct 19
$232 total
Oct 18 - Oct 19
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
$123 nightly
The price is $139 total per night from Oct 18 to Oct 19
$139 total
Oct 18 - Oct 19
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
$225 nightly
The price is $253 total per night from Nov 16 to Nov 17
$253 total
Nov 16 - Nov 17
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 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 ...
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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
Chesapeake Beach Resort
5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Great location"
A verified traveler stayed at Chesapeake Beach Resort
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