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Holiday Homes in Upper Matecumbe Key

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Our top choices for Upper Matecumbe Key holiday homes

Holiday Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (29)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is NZ$781
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Home in Key Largo

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 NZ$826
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Pool, Beach, Dock, Kayaks
9.6 out of 10, Exceptional, (84)
"Very quiet and cozy "
United States
Stephanie T.
The price is NZ$752
includes taxes & fees
7 Jan - 8 Jan 2026
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.8 out of 10, Exceptional, (11)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
The price is NZ$707
includes taxes & fees
7 Jan - 8 Jan 2026
4. Cozy Waterfront Apartment in Key Largo!
2.0 star property
10.0 out of 10, Exceptional, (46)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is NZ$1,012
includes taxes & fees
12 Jan - 13 Jan 2026
NEW ! Lagoon-front townhouse with Marina in Key Largo

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 NZ$1,357
includes taxes & fees
3 Jan - 4 Jan 2026
Ohana Cay 2brm/2bth - Book your getaway!
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 NZ$1,521
includes taxes & fees
25 Jan - 26 Jan 2026
Sunrise Escape - Ocean Front Villa - Sleeps 10
The price is NZ$2,697
includes taxes & fees
11 Jan - 12 Jan 2026
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
10.0 out of 10, Exceptional, (2)
"Everything was great "
United States
Ravone L.
The price is NZ$1,505
includes taxes & fees
5 Jan - 6 Jan 2026
New Oceanside Paradise with Pool and Waterfront Views!
9.2 out of 10, Wonderful, (11)
"Me my wife and 2 kids 18 & 19 had a great time. Loved the lagoon and the local places to eat and drink. "
United States
Craig H.
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
2.0 star property
7.6 out of 10, Good, (8)
"Great location with private beach loved it "
United States
Bobby A.
The price is NZ$1,736
includes taxes & fees
11 Jan - 12 Jan 2026
The Coral House - Bayside Retreat for 6-8 guests

Holiday Home in Key Largo

Keys Relaxing Getaway
10.0 out of 10, Exceptional, (57)
"All new and very clean. Great place to stay."
United States
M D.
Keys Relaxing Getaway
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 NZ$1,100
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
10.0 out of 10, Exceptional, (2)
" We regret that we only booked for one night. We will definitely return for a longer stay. Everything about Key Largo Resort was perfect! The setting, the location, the accommodations, everything! Thank you for an amazing experience! We will be back! "
United States
Kimberly V.
The price is NZ$1,150
includes taxes & fees
11 Jan - 12 Jan 2026
Serene Bungalow in Paradise at Largo Resort
The price is NZ$985
includes taxes & fees
4 Jan - 5 Jan 2026
2-bedroom townhome in pleasant gated community located in Key Largo
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 NZ$1,156
includes taxes & fees
13 Jan - 14 Jan 2026
Tranquil Bungalow at the Beautiful at Largo Resort
9.6 out of 10, Exceptional, (4)
"would stay again"
United States
Jonathan G.
The price is NZ$3,695
includes taxes & fees
13 Jan - 14 Jan 2026
The Grand Lodge Right On The Water at Largo Resort
9.6 out of 10, Exceptional, (32)
"Great place to stay. Plenty of room for everyone. Lots to do at the resort. "
United States
Tandy T.
The price is NZ$1,814
includes taxes & fees
7 Jan - 8 Jan 2026
SPACIOUS 4/3.5 VILLA! INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT 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 NZ$805
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Tropical House By The Shore at Largo 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

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Holiday Homes information

Number of reviews
680
Accommodation
665 Holiday Homes
Lowest Price
NZ$707
Highest Price
NZ$3,695

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