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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 23 to Jul 24
$674 total
Jul 23 - Jul 24
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
$320 nightly
The price is $361 total per night from Aug 21 to Aug 22
$361 total
Aug 21 - Aug 22
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. ...
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."

Reviewed on Jul 20, 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
$183 nightly
The price is $206 total per night from Aug 12 to Aug 13
$206 total
Aug 12 - Aug 13
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 ...
"One of my favorite places to have a relaxing trip with the family"

Reviewed on Jul 21, 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 ...
"Loved everything"

Reviewed on Jul 22, 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 10 to Aug 11
$141 total
Aug 10 - Aug 11
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 ...
"Clean, well laid out property. Nice area at waters edge to relax."

Reviewed on Jul 18, 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
$220 nightly
The price is $248 total per night from Aug 11 to Aug 12
$248 total
Aug 11 - Aug 12
Total includes 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 ...
"Espectacular"

Reviewed on Jul 21, 2025

Amara 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
$195 nightly
The price is $220 total per night from Jul 28 to Jul 29
$220 total
Jul 28 - Jul 29
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, ...
"Marilyn in the lobby was amazing! She was so attentive and helpful. All the staff was super friendly and accommodating! I would definitely stay here again."

Reviewed on Jul 20, 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
$145 nightly
The price is $161 total per night from Jul 27 to Jul 28
$161 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.
"Location"

Reviewed on Jul 18, 2025

Breezy Palms Resort
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
$147 nightly
The price is $166 total per night from Aug 18 to Aug 19
$166 total
Aug 18 - Aug 19
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 ...
Gem in Islamorada
"I love this place, it’s chill, dog friendly, ramp and docks for ease of throwing in my paddleboard. Insanely beautiful views, and central to everything."

Reviewed on Jul 17, 2025

Hadley Resort and Marina
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Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Islander Resort

Islander Resort

5 out of 5
Posted 8 hours ago
Travelocity Verified Review
"Loved everything "
A verified traveler stayed at Islander Resort
Islander Resort
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