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Jun 12 - Jun 14
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Top Lower Matecumbe Key hotels

Next available - August 2026 - Oceanfront - Heated Pool - Dock

Next available - August 2026 - Oceanfront - Heated Pool - Dock

Islamorada FL
This vacation home features an outdoor pool and a rooftop terrace. WiFi in public areas is free. A garden, laundry facilities, and barbecue grills are also on ...
"By far the best host I’ve encountered! The house was even more beautiful than the pictures and the water was magical! The kitchen and home has all you need. Highly recommend"

Reviewed on May 18, 2026

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Opens in a new windowNext available - August 2026 - Oceanfront - Heated Pool - Dock
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
A marina and a restaurant are featured at this smoke-free condo. Enjoy the outdoor pool and perks like free self parking and free WiFi. A picnic area and barbecue ...
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."

Reviewed on May 31, 2026

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Opens in a new windowCaloosa Cove Resort by CoolVacay
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jun 14 to Jun 15
$329 total
Jun 14 - Jun 15
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 ...
"Un poco costosa para lo que era pero todo bien"

Reviewed on Jun 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
$264 nightly
The price is $297 total per night from Jun 7 to Jun 8
$297 total
Jun 7 - Jun 8
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. ...
"Cheeca Lodge is my absolute favorite place in The Keys The property is gorgeous, I love the amenities, the complimentary kayaking, bikes & champagne for Mother’s Day was such a nice touch The rooms are so cozy, just love it there. Ask for Rob at the pool bar, he makes a great drink!"

Reviewed on Jun 4, 2026

Opens in a new windowCheeca 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
$233 nightly
The price is $262 total per night from Jun 9 to Jun 10
$262 total
Jun 9 - Jun 10
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 resort is in a great location, clean and well maintained. Our king suite was very comfortable, had a large, lovely bathroom, balcony with a great view of the ocean. Breakfast with made to order omelets and pancakes, as well as breads, muffins, cold cereals, juices, and a nice area to eat on the ..."

Reviewed on Jun 5, 2026

Opens in a new windowChesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Jun 14 to Jun 15
$224 total
Jun 14 - Jun 15
Total with taxes and fees
This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor ...
"This was a wonderful place to stay!!"

Reviewed on Jun 4, 2026

Opens in a new windowLime Tree Bay Resort
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
A private beach and an outdoor pool are featured at this smoke-free resort. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
"The room was not soundproof at all, and there was no dishwasher in the kitchen. Also, the air conditioner was very noisy, and it was quite inconvenient to go upstairs."

Reviewed on Jun 2, 2026

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Opens in a new windowMatecumbe Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$247 nightly
The price is $278 total per night from Jul 7 to Jul 8
$278 total
Jul 7 - Jul 8
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 ...
"Beautiful place"

Reviewed on Jun 6, 2026

Opens in a new windowAmara Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $333 total per night from Jun 22 to Jun 23
$333 total
Jun 22 - Jun 23
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
"I didn’t like there was no microwave and nothing to do if it was raining"

Reviewed on Jun 5, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
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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 Lower Matecumbe Key hotel reviews by fellow wanderers

Amara Cay Resort

Amara Cay Resort

5 out of 5
Posted 12 hours ago
Travelocity Verified Review
"Beautiful place"
A verified traveler stayed at Amara Cay Resort
Amara Cay Resort

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