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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
$232 nightly
The price is $261 total per night from May 4 to May 5
$261 total
May 4 - May 5
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 loved our stay, the staff was very friendly specially the 2 gentlemen that were in the breakfast. The hotel was very well maintained and peaceful. Our room was excellent the only complain I have is the A/C hitting our bed directly. But other than that I would stay here again.

Reviewed on Apr 29, 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
$312 nightly
The price is $351 total per night from May 14 to May 15
$351 total
May 14 - May 15
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. ...
We had an ocean front room in the new wing and can honestly say it was lovely. The staff were great, the hotel facilities were lovely and food and drinks all good.

Reviewed on Apr 28, 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$269 nightly
The price is $303 total per night from May 17 to May 18
$303 total
May 17 - May 18
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 ...
Overall, we had a wonderful stay at the Islander Resort. Since we visited on a Sunday night, dining options on the property were somewhat limited. However, we highly recommend the Lorelei Restaurant just across the street—it offers excellent food and drinks, live music, and truly stunning sunset ...

Reviewed on Apr 29, 2026

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$173 nightly
The price is $195 total per night from May 17 to May 18
$195 total
May 17 - May 18
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 ...
Parking handy. The A/C was older and made a bit of noise but it kept a good temp.

Reviewed on Apr 26, 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 4 to May 5
$252 total
May 4 - May 5
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 ...
Excellent stay, friendly staff and excellent location on the bayside of the Key. Great views and lots of chairs and recliners to take in the views.

Reviewed on Apr 22, 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
$249 nightly
The price is $280 total per night from May 11 to May 12
$280 total
May 11 - May 12
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 ...
We had the most amazing stay at Amara Cay in Islamorada for our honeymoon! From the moment we arrived, everything felt effortless, relaxing, and truly special. The property is absolutely beautiful—clean, modern, and perfectly captures that laid-back luxury island vibe. The rooms were comfortable ...

Reviewed on Apr 29, 2026

Opens in a new windowAmara Cay Resort
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
$137 nightly
The price is $154 total per night from May 13 to May 14
$154 total
May 13 - May 14
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.
Room was very clean and the bed was fantastically comfortable! Furniture was a bit out dated and not as comfortable as I would have liked. Pool was fantastic as well!

Reviewed on Apr 26, 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
$234 nightly
The price is $264 total per night from May 13 to May 14
$264 total
May 13 - May 14
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, ...
It was simply stunning. Beautiful location, great facilities, spacious apartment and for a family of 5 the door key card being on the wristband is genius. Thank you for a wonderful stay

Reviewed on Apr 21, 2026

Opens in a new windowLa Siesta Resort & Villas
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
$164 nightly
The price is $185 total per night from May 5 to May 6
$185 total
May 5 - May 6
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 ...
Breakfast was poor air conditioner was noisy staff was good

Reviewed on Apr 29, 2026

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.

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