Explore top 2026 4 Star Hotels in Upper Matecumbe Key

Name: Condo in the Keys
Rating: 8

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Top Upper Matecumbe Key 4 Star hotels

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

Fully refundableReserve now, pay when you stay

$264 nightly

$295 total

Aug 17 - Aug 18

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. ...

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

97000 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$302 nightly

$340 total

Aug 24 - Aug 25

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! (1,167 reviews)

"My family stayed for two nights and we wished our stay was longer. The kids enjoyed the pool, beach, water activities and we enjoyed the restaurants as well. It was great that a lot of the extras was pleasantly surprised"

Reviewed on Aug 9, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$220 nightly

$248 total

Aug 16 - Aug 17

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! (1,305 reviews)

"It was clean, family friendly, quiet but yet plenty to do. It’s island time so sometimes when you want to do an activity like kayaking the employees take their time or when the coffee runs out in the main lobby it can be a guessing game as to who will fill it. We loved our stay though and they were ..."

Reviewed on Aug 11, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$277 nightly

$312 total

Sep 2 - Sep 3

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 ...

Playa Largo Resort & Spa, Autograph Collection

97450 Overseas Highway Key Largo FL

Fully refundableReserve now, pay when you stay

$288 nightly

$324 total

Aug 30 - Aug 31

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 ...

9/10 Wonderful! (1,008 reviews)

"Very cool resort. Nice beach access and wonderful pool all on the same close area."

Reviewed on Aug 10, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$272 nightly

$306 total

Aug 17 - Aug 18

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 ...

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$237 nightly

$266 total

Aug 13 - Aug 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, ...

Villas At Hawks Cay Resort

61 Hawks Cay Boulevard Marathon FL

Fully refundableReserve now, pay when you stay

$830 nightly

$934 total

Aug 12 - Aug 13

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. ...

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$420 nightly

$473 total

Aug 16 - Aug 17

Total with taxes and fees

A marina, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Spend a day at the beach kayaking, or relax with sun loungers and beach ...

9.6/10 Exceptional! (79 reviews)

"Very helpful staff and all amenities are in excellent usable condition. The villas and the suites are very comfortable with beautiful comfortable bathrooms."

Reviewed on Aug 3, 2026

Condo in the Keys

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! (16 reviews)

"We had an absolutely wonderful stay and couldn’t have been happier with this condo. The location is excellent, close to everything while still offering a peaceful, relaxing atmosphere. The condo itself is beautifully decorated with a tasteful beach theme that immediately makes you feel like you’re ..."

Reviewed on Aug 1, 2026

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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.