A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Holiday Homes in Upper Matecumbe Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Upper Matecumbe Key holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$737
includes taxes & fees
1 Oct - 2 Oct
Little Peace of Haven
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is NZ$717
includes taxes & fees
1 Oct - 2 Oct
Charming Home in Key Largo
A coastal area with clear water, a sandy beach, and a small island with buildings.

3. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (51 reviews)
"We had a nice stay"
United States
Kevin M.
The price is NZ$513
includes taxes & fees
1 Oct - 2 Oct
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

4. 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, (24 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is NZ$727
includes taxes & fees
1 Oct - 2 Oct
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A modern kitchen with a built-in microwave, stove, and dishwasher.

5. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"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$614
includes taxes & fees
1 Oct - 2 Oct
4. Cozy Key Largo Waterfront Studio | Dive
A kitchen with white cabinets, a black stove, and a granite countertop.

6. Cozy 1-bedroom bungalow in gorgeous Key Largo with AC

Cozy 1-bedroom bungalow in gorgeous Key Largo with AC
Rock Harbor
The price is NZ$395
includes taxes & fees
1 Oct - 2 Oct
Cozy 1-bedroom bungalow in gorgeous Key Largo with AC
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

7. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (73 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is NZ$1,398
includes taxes & fees
14 Oct - 15 Oct
Sunrise Escape - Ocean Front Villa - Sleeps 10
A coastal residential area with a marina, modern buildings, and a swimming pool.

8. 1. Key Largo Waterfront Studio | Canal & Ocean

1. Key Largo Waterfront Studio | Canal & Ocean
Key Largo
9.4 out of 10, Exceptional, (13 reviews)
"Nice location. Enjoyed our stay. "
United States
David C.
The price is NZ$635
includes taxes & fees
7 Oct - 8 Oct
1. Key Largo Waterfront Studio | Canal & Ocean
A beach with a wooden structure and a signpost indicating directions to various locations.

9. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (67 reviews)
"The pool was clean and enjoying "
United States
Aaron G.
The price is NZ$1,113
includes taxes & fees
14 Oct - 15 Oct
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

10. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Beach Residence Private Overwater Dock Heated Pool Mahi Key
2.0 star property
Matecumbe
The price is NZ$4,334
includes taxes & fees
14 Oct - 15 Oct
Beach Residence Private Overwater Dock Heated Pool Mahi Key
Beach

11. Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (150 reviews)
"Beautiful, clean home. Loved the property and the inlet with all the fish was amazing. Would stay again."
United States
Sandra C.
Key Largo Villa, Kawama P6, 3/3
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

12. 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, (55 reviews)
"Very nice villa "
United States
Grace L.
The price is NZ$854
includes taxes & fees
1 Oct - 2 Oct
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
BBQ charcoal grills and tikies by the ocean

13. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 reviews)
"Great place to stay"
United States
Eric B.
The price is NZ$1,102
includes taxes & fees
1 Oct - 2 Oct
Oceanside Kawama Villa R5
A modern indoor space with a pool, white wicker furniture, and a white crib.

14. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is NZ$987
includes taxes & fees
1 Oct - 2 Oct
El Encanto: private saltwater pool & tiki lounge
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

15. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (230 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
The price is NZ$1,012
includes taxes & fees
5 Oct - 6 Oct
Key Largo Kawama Villa L1, 3/3
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

16. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (68 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is NZ$999
includes taxes & fees
7 Oct - 8 Oct
Key Largo Villa, Kawama K5, 3/3
A marina with boats docked, thatched-roof structures, and a view of the water.

17. Key Largo Tiny House, Marina, Beach + Pool Access

Key Largo Tiny House, Marina, Beach + Pool Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Everything was great, especially The Newman Hospitality Company who I dealt with. Great customer service!"
United States
Brittany C.
The price is NZ$537
includes taxes & fees
1 Oct - 2 Oct
Key Largo Tiny House, Marina, Beach + Pool Access
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

18. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is NZ$1,430
includes taxes & fees
28 Oct - 29 Oct
Oceanside Retreat w/Rooftop, Pool & Kayaks
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

19. 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 NZ$1,481
includes taxes & fees
7 Oct - 8 Oct
New Oceanside Paradise with Pool and Waterfront Views!
A coastal area with clear water, a sandy beach, and a small island with buildings.

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

New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"Tiny HomeThis tiny home was comfortable, clean, and fully stocked with all you need to vacation in the Keys! At first, I was hesitant on booking a tiny home coming from a 3,200sqft house but we found the layout functional and actually cozy with good amounts of space.I would recommend the place along with the property management team who ensured all communications were answered quickly and thoroughly!Would stay here again!"
United States
Christina R.
The price is NZ$523
includes taxes & fees
1 Oct - 2 Oct
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Every single detail was amazing. Staff was very kind and professional specially Tyanna from the front desk."
Kenia 1-night trip
Posted 17 hours ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Holiday Homes information

Number of reviews
906
Accommodation
624 Holiday Homes
Lowest Price
NZ$513
Highest Price
NZ$4,334

Explore a world of travel with Expedia