Upper Matecumbe Key Vacation Rentals from ₩146,746: Search Short-Term Rentals

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

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Our top choices for Upper Matecumbe Key vacation rentals

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

1. Breezy Palms Resort

Matecumbe

Zack

₩146,746 total

includes taxes & fees

Oct 4 - Oct 5

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Islamorada

Laura

₩368,205 total

includes taxes & fees

Oct 5 - Oct 6

A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

3. Premium Floating Bungalow by Stay Ombi

Key Largo

Deivys

₩1,100,284 total

includes taxes & fees

Oct 16 - Oct 17

A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

4. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Matecumbe

₩3,294,720 total

includes taxes & fees

Oct 14 - Oct 15

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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"We really enjoyed our stay except for rain"

Amara Cay Resort

8/10 Good

"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upper Matecumbe Key vacation rentals

1. Breezy Palms Resort

2. Treasure Harbor

3. Premium Floating Bungalow by Stay Ombi

4. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Find vacation rentals that suit your style

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Lime Tree Bay Resort

The Pelican Key Largo Cottages

Bayside Inn Key Largo

Islander Resort

Hadley Resort and Marina

Amara Cay Resort

Casa Morada

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