Holiday Homes in Lower Matecumbe Key

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Featured Holiday Homes in Lower Matecumbe Key

Relax in style with two Adirondack chairs and a charming wooden table, perfect for al fresco dining or unwinding.

"Great stay, great property, super comfortable.With 2 boys, the bunk beds were perfect!"

Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

"Everything just great except need better vaccum"

Relax by the ocean with a clear view, lounge chairs, and a curved pool surrounded by lush greenery.

"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"

Enjoy ocean views from the resort's two-story buildings with balconies.

"Great location. Beautiful, comfortable accommodations. Would absolutely return. "

Kitchen features a central island with a countertop, surrounded by cabinetry and a refrigerator, microwave, and oven.

"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "

includes taxes & fees

13 Aug - 14 Aug

Boats docked in a tranquil marina surrounded by palm trees and a white fence.

"Beautiful place in the keys, and felt larger than the photos showed. Owner is very communicative! "

"This property was amazing basically brand new definitely recommend "

Relax by the pool under the stars, surrounded by lush trees and a thatched-roof structure.

"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."

Stroll up to the charming front porch, surrounded by lush greenery and a beautiful tree.

"Great location of home. Easy to find. Quiet neighborhood. Plenty of parking spots available. Great views from both decks. Two clean bedrooms and 2 bathrooms. Plenty of stocked towels. Washer and dryer convenience with laundry soap available Very clean kitchen with soaps for dishes. Was missing pot holders and kitchen dish towel. Living area space and dining area a plus.Can’t wait to come back. "

Classic two-story home with a charming front porch and beautifully manicured lawns.

"Quiet, clean, neighborhood feel."

Relax by the pool surrounded by lush greenery and comfortable lounge seating.

"We loved the beautiful Gulf views and fishing and swimming and all this property has to offer. Great location too. The screened in porch overlooking the gulf was my favorite spot. We would definitely rent again. "

Relax by the resort's pool surrounded by lush greenery and comfortable lounge chairs.

"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "

Enjoy a beach view from the large windows in this room, featuring a seating area with a sofa and armchairs.

Relax by the pool surrounded by lush tropical vegetation and a marina view.

"Was a nice property and pleasant enough for our stay."

Stunning two-story building with a central entrance and balcony, set amidst lush greenery and palm trees.

"The property was very clean. The kitchen was well equipped and the beds were very comfortable. "

includes taxes & fees

5 Aug - 6 Aug

"Great place to stay and relax! "

Relax by the pool surrounded by palm trees and shaded by green umbrellas.

"Great trip. Very comfortable for family of 5. Cabana club lovely and great recommendations!"

Enjoy a tranquil beachfront setting with a clear ocean view, perfect for relaxation or dining.

"Great sunsets; quiet street; fantastic marine life. Frank was very responsive. The property is not brand new but delivered on what we needed: pool, great dock for fishing and keeping boat during day. Booked again for next year. "