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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
$238 nightly
The price is $268 total per night from Jun 8 to Jun 9
$268 total
Jun 8 - Jun 9
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 Villas are great! Nice and clean/ modern We had an amazing time with my elderly parents and my litte kids.

Reviewed on May 12, 2026

Opens in a new windowChesapeake Beach 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
$249 nightly
The price is $280 total per night from May 21 to May 22
$280 total
May 21 - May 22
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. ...
Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$264 nightly
The price is $297 total per night from Jun 1 to Jun 2
$297 total
Jun 1 - Jun 2
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 ...
I think some of the outdoor cushions could be updated.

Reviewed on May 13, 2026

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$180 nightly
The price is $203 total per night from May 28 to May 29
$203 total
May 28 - May 29
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage ...
Had a nice stay. Very convenient location for restaurants and our event. I would give 5 stars but the air conditioner in our room was very loud.

Reviewed on May 12, 2026

Opens in a new windowSunset Inn
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$224 nightly
The price is $252 total per night from May 17 to May 18
$252 total
May 17 - May 18
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 ...
For the price it could be better. Rooms close to road are load. Bathroom needs updating

Reviewed on May 10, 2026

Opens in a new windowLa Jolla Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$253 nightly
The price is $284 total per night from May 19 to May 20
$284 total
May 19 - May 20
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 ...
This hotel is a secret gem. The minute you arrive the friendly staff let you realize you are away. The beach, pool, fire pits in the eve all just make the vibe incredible. We continue to return!! Pet friendly!!!!

Reviewed on May 12, 2026

Opens in a new windowAmara Cay Resort
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
$251 nightly
The price is $282 total per night from May 20 to May 21
$282 total
May 20 - May 21
Total with taxes and fees
This hotel features 3 restaurants, a bar/lounge, and an outdoor pool. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free ...
La propiedad me encantó, muy limpia y bonita. Para el precio está muy bien, sin duda volvería

Reviewed on May 10, 2026

Opens in a new windowBayside Villas by Islander Resort
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from May 27 to May 28
$178 total
May 27 - May 28
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.
We stayed for 3 days. Breezy Palm is small quite and on the beach. Very clean and cozy. They have Boat rentals available. Great place to lounge in the sun. Nice breeze coming off the water. Plenty of parking. Will stay again on future trips to the Keys.

Reviewed on May 13, 2026

Opens in a new windowBreezy Palms 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
$232 nightly
The price is $261 total per night from May 27 to May 28
$261 total
May 27 - May 28
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, ...
We stayed for mother’s day and we had a good time there. Staff were very friendly

Reviewed on May 12, 2026

Opens in a new windowLa Siesta Resort & Villas
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Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Breezy Palms Resort

Breezy Palms Resort

4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"We stayed for 3 days. Breezy Palm is small quite and on the beach. Very clean and cozy. They have Boat rentals available. Great place to lounge in the sun. Nice breeze coming off the water. Plenty of parking. Will stay again on future trips to the Keys."
A verified traveler stayed at Breezy Palms Resort
Breezy Palms Resort

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