Upper Matecumbe Key Vacation Rentals : Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Upper Matecumbe Key

"Laid back atmosphere with renovated rooms."

￥25,861 total

includes taxes & fees

Jun 22 - Jun 23

2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

"Absolutely outstanding resort. Legitimate 5 star property. "

￥96,696 total

includes taxes & fees

Jun 25 - Jun 26

25-inch flat-screen TV with digital channels, TV

"Very clean and great atmosphere "

￥45,322 total

includes taxes & fees

Jun 22 - Jun 23

Private beach, sun loungers, beach umbrellas, beach towels

"Amazing property and wonderful owners. Super nice people and definitely will be returning."

"The stay was great and the property manager Jenn was amazing. Would stay again"

"It was a very nice stay! Enjoyed the colorful fish in the lagoon, and the big lobster! It was a short walk to the jetty and beach."

On the beach, sun loungers, beach towels

"Property was as advertised, great view and a clean fresh interior. "

￥107,601 total

includes taxes & fees

Jul 18 - Jul 19

"Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. "

"We enjoyed our short stay but looking forward to going back."

￥60,078 total

includes taxes & fees

Jun 30 - Jul 1

"Everything just great except need better vaccum"

"Nice place, lots to do, great location, great views"

"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "

￥61,775 total

includes taxes & fees

Jun 30 - Jul 1

"Word can not explain the place everything was the best and would stay again and again "

￥48,699 total

includes taxes & fees

Jun 22 - Jun 23

"Great weather, clean accommodations, a few glitches that were quickly (mostly) resolved.Great pool, nice views, convenient location."

"We enjoyed our stay from beginning to end. The checking and check out was very smooth. Thank you so much!"

￥56,516 total

includes taxes & fees

Jun 19 - Jun 20

"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "

"My wife, sons (26,23) and a guest has a wonderful stay. The condo was clean and large enough to spread out. Marianne is an excellent host who promptly communicates. Loved it!"

"Beautiful view. Nice staying. I would recommend this place 100%"

"This was a great spot to enjoy a large part of the Keys chain. The location midway down the Keys gave us access to so much. The space was exactly what we needed. The area was lovely and the amenities on the property were fantastic. Julio was great to work with and responded to our questions and needs very quickly."

"Quiet, clean, neighborhood feel."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Find out more about Upper Matecumbe Key

Search for holiday rentals in Upper Matecumbe Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Upper Matecumbe Key using one of the methods below:

View our selection of featured holiday rentals in Upper Matecumbe Key
Use the map to find apartments and other holiday homes in the Upper Matecumbe Key neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Upper Matecumbe Key while they last

Look no further and take a look at our great range of rental properties in Upper Matecumbe Key!

Recent reviews of Upper Matecumbe Key properties

5/5 Excellent

"Perfect "

A verified traveler stayed at Hawks Cay Resort

Posted 8 hours ago

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

5/5 Excellent

"Wonderful stay. Beautiful place. Was very glad there was the hammock beach. The water sport beach was tons of kids. Was kinda crowded and loud. Hammock beach was quiet and beautiful. Even had drink service. Everyone was very nice. Would come again. Incredible resort. "

A verified traveler stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton

Posted 20 hours ago

5/5 Excellent

"Amara Cay Resort is truly a slice of paradise! Our stay was absolutely perfect — from the moment we checked in, we were greeted by friendly, helpful staff who made us feel right at home. We stayed in an oceanfront hotel room, and the views were nothing short of breathtaking. Waking up to the sound of the waves and watching the sunrise from our balcony was a highlight of the trip. Huge thanks to the entire team at Amara Cay for creating such a memorable experience. We’ll definitely be back! "

A verified traveler stayed at Amara Cay Resort

Posted 1 day ago