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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 AU$592
includes taxes & fees
29 Sept - 30 Sept
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 AU$514
includes taxes & fees
28 Sept - 29 Sept
Charming Home in Key Largo
A beach with a wooden structure and a signpost indicating directions to various locations.

3. 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 AU$882
includes taxes & fees
14 Oct - 15 Oct
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A marina with boats docked, thatched-roof structures, and a view of the water.

4. 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 AU$423
includes taxes & fees
30 Sept - 1 Oct
Key Largo Tiny House, Marina, Beach + Pool Access
A two-story building with a pool, a boat dock, and a table set for dining.

5. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is AU$1,391
includes taxes & fees
12 Oct - 13 Oct
Waterfront / Ocean Access Canal / Kamp Key / Homes

6. 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.
The price is AU$816
includes taxes & fees
26 Sept - 27 Sept
Key Largo Villa, Kawama P6, 3/3

7. Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2
Key Largo
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "
United States
Brooke B.
The price is AU$728
includes taxes & fees
26 Sept - 27 Sept
Kawama G12 Upscale OceansideVilla with Marina 2/2
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 AU$545
includes taxes & fees
29 Sept - 30 Sept
1. Key Largo Waterfront Studio | Canal & Ocean
A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

9. 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 AU$3,578
includes taxes & fees
14 Oct - 15 Oct
Beach Residence Private Overwater Dock Heated Pool Mahi Key
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

10. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (72 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is AU$1,120
includes taxes & fees
28 Sept - 29 Sept
Sunrise Escape - Ocean Front Villa - Sleeps 10
A modern kitchen with a built-in microwave, stove, and dishwasher.

11. 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 AU$477
includes taxes & fees
27 Sept - 28 Sept
4. Cozy Key Largo Waterfront Studio | Dive
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 AU$701
includes taxes & fees
28 Sept - 29 Sept
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

13. 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, (23 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is AU$622
includes taxes & fees
8 Oct - 9 Oct
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A wooden deck with lounge chairs, a pool, and a dock with boats.

14. Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (70 reviews)
"We were really impressed with the house - it had all the little things that made the stay so comfortable - reclining chairs in the living room, A/C in every room, a great outside deck complete with a big TV and clean, clean, clean."
United States
Ann
The price is AU$452
includes taxes & fees
30 Sept - 1 Oct
Waterfront Tiny House w Pool, Beach, and Boat Dock
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

15. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is AU$1,190
includes taxes & fees
18 Oct - 19 Oct
Oceanside Retreat w/Rooftop, Pool & Kayaks
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 AU$824
includes taxes & fees
7 Oct - 8 Oct
Key Largo Villa, Kawama K5, 3/3
A coastal area with clear water, a sandy beach, and a small island with buildings.

17. Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this RV over July 4th weekend in Key Largo. The location was perfect exactly what we were looking for. Everything about the property made for a great family getaway.Communication was a little confusing at first — it seemed like a different number was reaching out initially, and when I replied to that one, I didn’t hear back. Once I was in touch with the host’s actual number, though, communication was reliable. By that point we’d already figured out the answers to our...
United States
Jennifer A.
The price is AU$442
includes taxes & fees
26 Oct - 27 Oct
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

18. 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, (62 reviews)
"Especially enjoyed the private lagoon."
United States
Tom W.
The price is AU$872
includes taxes & fees
26 Sept - 27 Sept
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A coastal area with clear water, a sandy beach, and a small island with buildings.

19. 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, (50 reviews)
"We had a nice stay"
United States
Kevin M.
The price is AU$381
includes taxes & fees
29 Sept - 30 Sept
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

20. 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 AU$1,471
includes taxes & fees
18 Oct - 19 Oct
New Oceanside Paradise with Pool and Waterfront Views!
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

Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 4 hours ago
Casa Morada

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Holiday Homes information

Number of reviews
563
Accommodation
624 Holiday Homes
Lowest Price
AU$381
Highest Price
AU$3,578

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