A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Upper Matecumbe Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Upper Matecumbe Key vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (751 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
The price is ₩110,796
₩146,278 total
includes taxes & fees
Oct 4 - Oct 5
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is ₩134,765
₩344,794 total
includes taxes & fees
Sep 24 - Sep 25
Treasure Harbor
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is ₩275,396
₩309,822 total
includes taxes & fees
Sep 29 - Sep 30
Island Bay Resort
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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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."
J Cristina 1-night trip
Posted 4 hours ago
Chesapeake Beach Resort

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