Search Holiday Homes in Upper Matecumbe Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • 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

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (31 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is £343
includes taxes & fees
4 Mar - 5 Mar
Charming Home in Key Largo

Waterfront Pool, Beach, Dock, Kayaks

Waterfront Pool, Beach, Dock, Kayaks
Key Largo
9.6 out of 10, Exceptional, (81 reviews)
"Had a great time property was exactly as described. Would stay again."
United States
Michael S.
The price is £442
includes taxes & fees
25 Feb - 26 Feb
Waterfront Pool, Beach, Dock, Kayaks

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"Great location! Super quiet and relaxing area! "
United States
Devin H.
The price is £377
includes taxes & fees
26 Feb - 27 Feb
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (49 reviews)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is £568
includes taxes & fees
4 Mar - 5 Mar
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (68 reviews)
"Great place!"
United States
Jessica S.
The price is £926
includes taxes & fees
17 Mar - 18 Mar
Sunrise Escape - Ocean Front Villa - Sleeps 10

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (142 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is £676
includes taxes & fees
2 Mar - 3 Mar
Beautiful Kawama Townhouse

SPECIAL-2 Bed 2 Bath Villa including Cabana Club membership which

SPECIAL-2 Bed 2 Bath Villa including Cabana Club membership which
Marathon
9.8 out of 10, Exceptional, (144 reviews)
"Great location and very neat place!"
United States
FERNANDO S.
The price is £470
includes taxes & fees
1 Mar - 2 Mar
SPECIAL-2 Bed 2 Bath Villa including Cabana Club membership which

Casa Largo

Casa Largo
Key Largo
9.0 out of 10, Wonderful, (130 reviews)
"Very nice updated home in a nice community with views to the lagoon. Would definitely stay here again!"
United States
Priscilla G.
Casa Largo

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
Key Largo Village
The price is £968
includes taxes & fees
1 Mar - 2 Mar
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (172 reviews)
"Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!"
United States
Chandler G.
The price is £1,050
includes taxes & fees
18 Mar - 19 Mar
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (48 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is £600
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.6 out of 10, Excellent, (11 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is £601
includes taxes & fees
3 Mar - 4 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (32 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is £601
includes taxes & fees
3 Mar - 4 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Sunrise Bungalow w/Plenty of Shade at Largo Resort

Sunrise Bungalow w/Plenty of Shade at Largo Resort
Key Largo
The price is £399
includes taxes & fees
11 Mar - 12 Mar
Sunrise Bungalow w/Plenty of Shade at Largo Resort

New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Ravone L.
The price is £727
includes taxes & fees
1 Mar - 2 Mar
New Oceanside Paradise with Pool and Waterfront Views!

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Key Largo
9.2 out of 10, Wonderful, (15 reviews)
"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

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (195 reviews)
"Very relaxing vacation "
United States
Teresa M.
The price is £956
includes taxes & fees
16 Mar - 17 Mar
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (94 reviews)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
The price is £712
includes taxes & fees
28 Feb - 1 Mar
Ohana Cay 2brm/2bth - Book your getaway!

MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT

MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT
Rock Harbor
9.6 out of 10, Exceptional, (48 reviews)
"We had an absolutely wonderful experience at this condo. From the moment we arrived, everything was spotless, beautifully decorated, and even better than the listing photos. The space felt warm, inviting, and thoughtfully set up with all the comforts of home.The location was perfect: quiet, safe, and close to everything we needed. Whether we were relaxing inside or exploring the area, it truly felt like the ideal home base."
United States
Tracy D.
The price is £733
includes taxes & fees
6 Mar - 7 Mar
MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Rock Harbor
9.8 out of 10, Exceptional, (10 reviews)
"Incredible place to stay !! Hosts were great and it was just as described !! "
United States
Bruce N.
The price is £912
includes taxes & fees
5 Mar - 6 Mar
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
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.

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.
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
1,074
Accommodation
665 Holiday Homes
Lowest Price
£343
Highest Price
£1,050

Explore a world of travel with Expedia