4 Stars Hotels in Upper Matecumbe Key: Compare Hotel Prices & Find the Cheapest Upper Matecumbe Key, Islamorada 4 Stars Hotels

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight

May 20 - May 21

Tomorrow

May 21 - May 22

This weekend

May 22 - May 24

Next weekend

May 29 - May 31

Our top choices for Upper Matecumbe Key 4-star hotels

3 outdoor pools, cabanas (surcharge), pool umbrellas

Hawks Cay Resort

Marathon

United States

Kathryne

NT$12,174 total

includes taxes & fees

Jun 7 - Jun 8

Property grounds

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

Key Largo

United States

Stephanie

NT$13,019 total

includes taxes & fees

Jun 14 - Jun 15

Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room

Amara Cay Resort

Matecumbe

United States

Robert

NT$9,504 total

includes taxes & fees

May 25 - May 26

Exterior

Islander Resort

Matecumbe

United States

TAXAID

NT$10,194 total

includes taxes & fees

Jun 10 - Jun 11

In-room safe, individually decorated, individually furnished

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

Islamorada

United States

Monica Jane

NT$11,368 total

includes taxes & fees

Jun 3 - Jun 4

Exterior

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Germany

Hanspeter

NT$13,917 total

includes taxes & fees

Jun 9 - Jun 10

Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

La Siesta Resort & Villas

Matecumbe

United States

Yadaris

NT$9,504 total

includes taxes & fees

May 26 - May 27

3 outdoor pools, cabanas (surcharge), pool umbrellas

Villas At Hawks Cay Resort

Marathon

United States

Elise

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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Upper Matecumbe Key.

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

NT$8,587

NT$11,976 total

Jun 3 - Jun 4

includes taxes & fees

9.2/10 Wonderful! (1,319 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

See all hotels in Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

8/10 Good

"Close to beach. Lots of activities"

Amara Cay Resort

Amara Cay Resort

10/10 Excellent

"Absolutely loved this resort! Amazing service and Happy Hour at the Pool! Excellent Transportation options and within walking distance to some really nice restaurants. Great stay after 3 nights in Key West for our Anniversary. Hotel staff communicated with us to plan our arrival and was able to accommodate an early check in. It was a wonderful stay, just book it!"

Hawks Cay Resort

Hawks Cay Resort

8/10 Good

"All in all a good place to stay for the family. Grades: -Pools: Family and adult pools were available throughout the day, in good condition, and well serviced by the nearby tiki bar. (Grade A) -Service: Service in the overall resort depended on who you encountered. Some front desk members were quite helpful, others were low energy and doing the bare minimum. Same for restaurants. (Grade B) -Amenities: Amenities were plentiful with pickleball, tennis, and basketball courts. Multiple pools. A re-vamped workout room and spa area. Soon to be kids water park area. (Grade A+) -Lagoon: Lagoon for paddleboard, canoeing and swimming was not quite as picturesque as advertised. (Grade C) "

The Islands of Islamorada

The Islands of Islamorada

4/10 Poor

"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 and get coffee in the morning in the office or they would just bring up to us if we would like. When I called in the morning for coffee, they confirmed and then after a half hour I called again to see if I was still receiving the coffee and was told that the other attendant was picking up milk for the latte. To make things worse, I called the following day and was told I can’t get a coffee before 9 AM. Also, description on website/Hotels.com are inaccurate. It makes it seem like a beautiful beach and when we got there, we found out that you can’t just walk into the water. There are rocks and soft bottom in some areas which are just not feasible to swim in. If you are looking to swim in the ocean, will need to rent a boat. Also, pool area bar was barely open while we were there. Property was pretty empty, I do understand why. Front Office was very understanding of my complaints, but that did not do us any good. I really don’t understand what they meant by pampered, they really did not do anything for us. We did have dinner at a different resort nearby. Would definitely recommend that for the money. To be fair, room was very updated, clean and nice. Just not enough for money."

La Siesta Resort & Villas

La Siesta Resort & Villas

6/10 Okay

"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 there. Our room had black sharpie all over the floors. There were no cups, plates, silverware… to use with the small kitchen. The couch and drapes were dirty. The freezer was a block of ice. Need more hangers in the closet. The bicycles, kayaks were not available for use until 9:30am and had to be back by 4pm (hottest part of a Florida day). The snack shack/bar at the pool opened late and closed early. Our room was cleaned once in six days. For the cost I shouldn’t be typing any of this."

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