Book Hotels in Upper Matecumbe Key, FL

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Nov 13 - Nov 15
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Top Upper Matecumbe Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $214 total per night from Nov 10 to Nov 11
$214 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 ...
"We stayed for 2 nights at the Chesapeake Bay resort. Great location, Our room was clean and property was well maintained. The front desk staff was very welcoming and helpful. Easy check in and out. Beautiful views of the ocean from our balcony. Great amenities, breakfast each morning was delicious. ..."

Reviewed on Nov 8, 2026

Opens in a new windowChesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
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 ...
"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

Opens in a new windowIslander Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
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 Dec 1 to Dec 2
$263 total
Dec 1 - Dec 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. ...
"The suite had an odor like humidity not nice , I paid for a room with view they didn’t give that, anyway it was a nice suite but the odor killed the experience for me"

Reviewed on Nov 8, 2026

Opens in a new windowCheeca Lodge & Spa
La Jolla Resort

La Jolla Resort

2.5 out of 5
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

Opens in a new windowLa Jolla Resort
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $153 total per night from Nov 17 to Nov 18
$153 total
Nov 17 - Nov 18
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.
"Had a wonderful stay. Looking forward to staying longer next time."

Reviewed on Nov 8, 2026

Opens in a new windowBreezy Palms Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$222 nightly
The price is $250 total per night from Nov 17 to Nov 18
$250 total
Nov 17 - Nov 18
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 ...
Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
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, ...
Opens in a new windowLa Siesta Resort & Villas
Casa Morada

Casa Morada

3.5 out of 5
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 ...
Opens in a new windowCasa Morada
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
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 ...
Opens in a new windowHadley Resort and Marina
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Lowest 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.

Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Breezy Palms Resort

Breezy Palms Resort

4 out of 5
Posted 16 hours ago
Travelocity Verified Review
"Had a wonderful stay. Looking forward to staying longer next time."
A verified traveler stayed at Breezy Palms Resort
Breezy Palms Resort

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