Holiday Homes in Upper Matecumbe Key

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upper Matecumbe Key holiday homes

9.6 out of 10, Exceptional, (45)
"We absolutely loved it! "
United States
Emily B.
The price is AU$514
includes taxes & fees
15 Dec - 16 Dec
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Holiday Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (28)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is AU$723
includes taxes & fees
28 Dec - 29 Dec
Charming Home in Key Largo
9.6 out of 10, Exceptional, (83)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
United States
Brad W.
The price is AU$607
includes taxes & fees
15 Dec - 16 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Holiday Home in Key Largo

Casa Largo
9.0 out of 10, Wonderful, (129)
"We stayed in 2 vrbo properties while in Florida. This one met and exceeded our expectations. We would stay again without hesitation."
United States
Kelly M.
The price is AU$812
includes taxes & fees
14 Dec - 15 Dec
Casa Largo
2.0 star property
10.0 out of 10, Exceptional, (45)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is AU$793
includes taxes & fees
15 Dec - 16 Dec
NEW ! Marvelous 2-bedroom house with Marina in Key Largo
10.0 out of 10, Exceptional, (17)
"Our bungalow was very clean and the beds were very comfortable! It was almost like we we're on our own private island and my 8 year old loved it! We hope to come back on our next visit!"
United States
Elizabeth M.
The price is AU$1,085
includes taxes & fees
12 Jan - 13 Jan 2026
Lovely Bungalow w/ Plenty Of Shade at Largo Resort

Holiday Home in Rock Harbor

Ohana Cay 2brm/2bth - Book your getaway!
10.0 out of 10, Exceptional, (92)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
The price is AU$1,222
includes taxes & fees
3 Jan - 4 Jan 2026
Ohana Cay 2brm/2bth - Book your getaway!
9.6 out of 10, Exceptional, (7)
"10/10! This property itself is secluded and very safe. The pool and views were breathtaking. The complimentary paddle boards and bicycles were fun and just an extra service that bettered our experience. The employees were amazing, kind, and professional. The bungalow was so comfortable and smelt amazing when we entered. Beds were comfortable and the little kitchen was used! Plates, silverwear, & cups were provided thankfully. The host!!!! 100/10. Thank you!!!! She was able to provide a nice...
United States
Nancy H.
The price is AU$715
includes taxes & fees
18 Dec - 19 Dec
Tranquil Bungalow at the Beautiful at Largo Resort

Holiday Home in Key Largo

Beautiful Kawama Townhouse
9.8 out of 10, Exceptional, (140)
"Great location, well stocked kitchen, bathrooms, etc. Excellent host, had a great time in a beautiful community. The lagoon is a great feature."
United States
jannet p.
The price is AU$948
includes taxes & fees
15 Dec - 16 Dec
Beautiful Kawama Townhouse
10.0 out of 10, Exceptional, (4)
"Loved the location and views, house is amazing"
United States
Dan L.
The price is AU$1,191
includes taxes & fees
14 Dec - 15 Dec
Key Largo Oasis Oceanfront with Pool & Hot Tub

Holiday Home in Key Largo

Oceanside Kawama Villa R5
9.2 out of 10, Wonderful, (180)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
Oceanside Kawama Villa R5
9.6 out of 10, Exceptional, (63)
"Great little place with awesome outdoor area. "
United States
James D.
The price is AU$622
includes taxes & fees
15 Dec - 16 Dec
Waterfront Tiny House w Pool, Beach, and Boat Dock
9.4 out of 10, Exceptional, (46)
"This was a very cute resort, with perfect views! We were able to stay with our family and even bring our puppies. We had an absolutely amazing time!!"
United States
Shane F.
The price is AU$844
includes taxes & fees
18 Dec - 19 Dec
Waterfront Cottage - Beach and Dockage! Open Water Views!
The price is AU$2,390
includes taxes & fees
12 Jan - 13 Jan 2026
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
9.6 out of 10, Exceptional, (46)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is AU$810
includes taxes & fees
16 Dec - 17 Dec
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.8 out of 10, Exceptional, (66)
"This place was perfect for 9 people. Both the condo and the area had plenty to do "
United States
Ethan
The price is AU$1,755
includes taxes & fees
25 Dec - 26 Dec
Sunrise Escape - Ocean Front Villa - Sleeps 10
9.6 out of 10, Exceptional, (4)
"would stay again"
United States
Jonathan G.
The price is AU$2,973
includes taxes & fees
17 Dec - 18 Dec
The Grand Lodge Right On The Water at Largo Resort
9.6 out of 10, Exceptional, (123)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
The price is AU$662
includes taxes & fees
14 Dec - 15 Dec
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
9.0 out of 10, Wonderful, (2)
"We got everything we need, a relaxing place, great service, easy to find, restaurants all over the place and most important of all very clean and beautiful. We loved."
United States
Ricardo M.
The price is AU$1,645
includes taxes & fees
26 Dec - 27 Dec
Spacious Bungalow w/ Sunset Ocean View at Largo Resort

Holiday Home in Key Largo

Waterfront Pool, Beach, Dock, Kayaks
9.8 out of 10, Exceptional, (80)
"Had a great time property was exactly as described. Would stay again."
United States
Michael S.
The price is AU$696
includes taxes & fees
15 Dec - 16 Dec
Waterfront Pool, Beach, Dock, Kayaks
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Holiday Homes information

Number of reviews
1,144
Accommodation
683 Holiday Homes
Lowest Price
AU$514
Highest Price
AU$2,973

Explore a world of travel with Expedia