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Top Upper Matecumbe Key hotels

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$599 nightly
The price is $674 total per night from Jul 20 to Jul 21
$674 total
Jul 20 - Jul 21
Total includes taxes and fees
2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
"Great property. Very comfortable and luxurious. The bar and food options can delivered to the room and very tasty! Really enjoyed the stay. Charlene was a great bartender by the pool!"

Reviewed on May 4, 2025

The Islands of Islamorada
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $269 total per night from Aug 14 to Aug 15
$269 total
Aug 14 - Aug 15
Total includes 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. ...
"I was very friendly and attentive. Elijah was especially excellent at the front desk."

Reviewed on Jul 13, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $223 total per night from Jul 28 to Jul 29
$223 total
Jul 28 - Jul 29
Total includes 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 loved it!"

Reviewed on Jul 10, 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$268 nightly
The price is $302 total per night from Aug 11 to Aug 12
$302 total
Aug 11 - Aug 12
Total includes 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 ...
"Fabulous vacation experience! Beautiful facilites with phenomenal ocean views!!!"

Reviewed on Jul 10, 2025

Islander Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
$125 nightly
The price is $141 total per night from Aug 11 to Aug 12
$141 total
Aug 11 - Aug 12
Total includes 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 ...
"I love staying here! Old Florida charm and convenient to great restaurants!"

Reviewed on Jul 14, 2025

La Jolla Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $244 total per night from Aug 12 to Aug 13
$244 total
Aug 12 - Aug 13
Total includes taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a ...
"Large shower. Relaxing environment. Kayaks. Ability to use resort amenities until 4 on day of checkout. Room decorated for relaxation."

Reviewed on Jul 15, 2025

Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
$238 nightly
The price is $268 total per night from Aug 10 to Aug 11
$268 total
Aug 10 - Aug 11
Total includes 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, ...
"Excellent vacations, quiet place. Front Desk excellent attention. I general they have 100%."

Reviewed on Jul 15, 2025

La Siesta Resort & Villas
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $173 total per night from Jul 27 to Jul 28
$173 total
Jul 27 - Jul 28
Total includes 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.
"Our stay was pleasant. The staff is friendly. The property is an older property but fairly well maintained. Our unit was updated and clean. The only complaint I have is the hot water in the shower wouldn't hold steady."

Reviewed on May 28, 2025

Breezy Palms Resort
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
$156 nightly
The price is $175 total per night from Aug 11 to Aug 12
$175 total
Aug 11 - Aug 12
Total includes 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 ...
"We stayed in the “Villas” on our 2nd stay and it was comfortable at a very affordable price. This is an older hotel and villa we had was clean and the furniture was in good condition."

Reviewed on Jul 10, 2025

Hadley Resort and Marina
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