Explore top 2026 4 Star Hotels in Upper Matecumbe Key

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Top Upper Matecumbe Key 4 Star hotels

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd Marathon FL
$334 nightly
The price is $375 total per night from Jun 14 to Jun 15
$375 total
Jun 14 - Jun 15
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
8.2/10 Very Good! (1,003 reviews)
"Perfect getaway!"

Reviewed on May 22, 2026

Opens in a new windowHawks 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
$329 nightly
The price is $370 total per night from Jun 17 to Jun 18
$370 total
Jun 17 - Jun 18
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. ...
8.6/10 Excellent! (1,073 reviews)
"The room was very clean, the staff was very friendly. We would stay again"

Reviewed on May 21, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
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 26 to May 27
$284 total
May 26 - May 27
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 ...
8.8/10 Excellent! (1,272 reviews)
"Didn't like the seclusion cleanliness set up"

Reviewed on May 21, 2026

Opens in a new windowAmara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $304 total per night from May 31 to Jun 1
$304 total
May 31 - Jun 1
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 ...
9.2/10 Wonderful! (1,014 reviews)
"Close to beach. Lots of activities"

Reviewed on May 20, 2026

Opens in a new windowIslander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $359 total per night from Jun 1 to Jun 2
$359 total
Jun 1 - Jun 2
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
9/10 Wonderful! (198 reviews)
"My only suggestion is to clean the garbage littered in the beach-lounging area. There’s also litter in the ocean (under Little Limon deck) that we picked up and a strong smell of sewage that hits the nostrils as soon as we exit our room or walk towards the Tiki bar. The ice cream place also needs ..."

Reviewed on May 16, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$392 nightly
The price is $441 total per night from Jun 7 to Jun 8
$441 total
Jun 7 - Jun 8
Total with taxes and fees
This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the ...
8.8/10 Excellent! (1,001 reviews)
"The staff here is outstanding. They are professional and will go out of their way to accommodate the guest. The resort is amazing and provides a lot of events throughout the days. We will definitely be returning."

Reviewed on May 13, 2026

Opens in a new windowPlaya Largo Resort & Spa, Autograph Collection
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from May 27 to May 28
$266 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, ...
8.6/10 Excellent! (1,001 reviews)
"La Siesta has so much potential. Beautiful grounds, spacious rooms, pool and views. The front counter staff and bike staff were very nice. Unfortunately they don’t clean up the trash around the compound. To either side of our entrance was trash that had been there before us and Is probably still ..."

Reviewed on May 17, 2026

Opens in a new windowLa Siesta Resort & Villas
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
61 Hawks Cay Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
$744 nightly
The price is $837 total per night from May 28 to May 29
$837 total
May 28 - May 29
Total with taxes and fees
This luxury resort features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
8.2/10 Very Good! (203 reviews)
"The property was beautiful, clean, and a short distance from many great adventures in the keys."

Reviewed on May 16, 2026

Opens in a new windowVillas At Hawks Cay Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$624 nightly
The price is $702 total per night from May 27 to May 28
$702 total
May 27 - May 28
Total with taxes and fees
A marina, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
9.6/10 Exceptional! (76 reviews)
"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on May 18, 2026

Opens in a new windowThe Islands of Islamorada
Condo in the Keys

Condo in the Keys

4 out of 5
500 Burton Dr Tavernier FL
The private beach and full-service spa are among the highlights at this apartment. There's fun for all ages with a playground and an arcade/game room, and families ...
8/10 Very Good! (14 reviews)
"Nice kitchen. Great view."

Reviewed on Mar 27, 2026

Opens in a new windowCondo in the Keys
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4 Star Hotels Upper Matecumbe Key

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Upper Matecumbe Key 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Upper Matecumbe Key will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Upper Matecumbe Key, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

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