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
$204 nightly
The price is $229 total per night from Nov 19 to Nov 20
$229 total
Nov 19 - Nov 20
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 ...
"The office attendant was super nice"
Reviewed on Nov 12, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $282 total per night from Nov 15 to Nov 16
$282 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 ...
"Sunrise was beautiful. Loved the private seating out back. Arrived at night and it is not well signed or lit. Bathroom layout with the sink in the bedroom was odd and there was no vanity space to set anything. Menu at the resteraunt was limited. Not all items were available. The value for the money ..."
Reviewed on Nov 10, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$147 nightly
The price is $165 total per night from Nov 15 to Nov 16
$165 total
Nov 15 - Nov 16
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.
"Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent"
Reviewed on Nov 9, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from Nov 15 to Nov 16
$266 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, ...
"Nice place, helpful staff, plenty of places to relax or just hang out."
Reviewed on Nov 11, 2026
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $200 total per night from Nov 29 to Nov 30
$200 total
Nov 29 - Nov 30
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 ...
"Quaint little hotel, close to lots of restaurants. My only suggestion to them would be that breakfast/coffee be available earlier. They don’t open til 8 am and several days we had early excursions and would have like coffee and something quick for breakfast"
Reviewed on Nov 9, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $268 total per night from Nov 16 to Nov 17
$268 total
Nov 16 - Nov 17
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
$222 nightly
The price is $250 total per night from Nov 15 to Nov 16
$250 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 ...
La Jolla Resort
82216 Overseas Highway Islamorada FL
$169 nightly
The price is $190 total per night from Nov 18 to Nov 19
$190 total
Nov 18 - Nov 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 ...
Casa Morada
82200 overseas HWY Islamorada FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Nov 16 to Nov 17
$241 total
Nov 16 - Nov 17
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
Chesapeake Beach Resort
5 out of 5
Posted 11 hours ago
Travelocity Verified Review
"The office attendant was super nice"
A verified traveler stayed at Chesapeake Beach Resort
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