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
$248 nightly
The price is $280 total per night from Nov 15 to Nov 16
$280 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 ...
"We absolutely loved our stay at Islander! It was such a peaceful, relaxing resort, and we’re so glad we chose it for our honeymoon. The staff was incredibly helpful and welcoming, and the shuttle service was a wonderful perk for getting to and from nearby restaurants. We also really enjoyed the resort’s ..."
Reviewed on Nov 5, 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 29 to Nov 30
$263 total
Nov 29 - Nov 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. ...
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely ..."
Reviewed on Nov 8, 2026
La Jolla Resort
82216 Overseas Highway Islamorada FL
$152 nightly
The price is $171 total per night from Nov 18 to Nov 19
$171 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 ...
"Nice clean and comfortable room with kitchen. Staff were friendly and helpful. Grounds were landscaped nicely."
Reviewed on Nov 7, 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 Nov 10 to Nov 11
$215 total
Nov 10 - Nov 11
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 ...
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 ...
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $138 total per night from Nov 10 to Nov 11
$138 total
Nov 10 - Nov 11
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
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, ...
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 ...
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $189 total per night from Nov 10 to Nov 11
$189 total
Nov 10 - Nov 11
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
Cheeca Lodge & Spa
5 out of 5
Posted 6 hours ago
Travelocity Verified Review
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely recommend."
A verified traveler stayed at Cheeca Lodge & Spa
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