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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Upper Matecumbe Key vacation 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
9.0 out of 10, Wonderful, (6 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is ￥23,807
￥65,489 total
includes taxes & fees
Nov 30 - Dec 1
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 ￥22,703
￥64,877 total
includes taxes & fees
Nov 1 - Nov 2
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, (54 reviews)
"We had a nice stay"
United States
Kevin M.
The price is ￥17,860
￥52,610 total
includes taxes & fees
Nov 5 - Nov 6
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beach

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (151 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 ￥39,415
￥89,590 total
includes taxes & fees
Nov 1 - Nov 2
Key Largo Villa, Kawama P6, 3/3
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

5. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is ￥43,526
￥123,611 total
includes taxes & fees
Dec 1 - Dec 2
Sunrise Escape - Ocean Front Villa - Sleeps 10
A wooden deck with lounge chairs, a pool, and a dock with boats.

6. 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 ￥29,394
￥67,005 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront Tiny House w Pool, Beach, and Boat Dock
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

7. Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa

Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa
Key Largo
9.4 out of 10, Exceptional, (231 reviews)
"This vila was perfect for our stay! It was centrally located, clean, well stocked kitchen."
United States
Debra J.
The price is ￥44,145
￥89,031 total
includes taxes & fees
Nov 1 - Nov 2
Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

8. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is ￥74,494
￥149,649 total
includes taxes & fees
Nov 12 - Nov 13
Oceanside Retreat w/Rooftop, Pool & Kayaks
A coastal area with clear water, a sandy beach, and a small island with buildings.

9. 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.
Key Largo Tiny House, Marina, Beach + Pool Access
A bedroom with a large bed, a desk, and a chair, a mirror, and decorative wall art.

10. Serenity Bungalow at Largo Resort

Serenity Bungalow at Largo Resort
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
" 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 ￥69,812
￥99,094 total
includes taxes & fees
Nov 10 - Nov 11
Serenity Bungalow at Largo Resort
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

11. 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.
Key Largo Villa, Kawama K5, 3/3
A modern kitchen with white cabinetry, a dining area with a white table and chairs, and a living room with a sofa and decorative pillows.

12. Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks

Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"Great little home to stay at!"
United States
Dave B.
The price is ￥22,139
￥55,533 total
includes taxes & fees
Nov 2 - Nov 3
Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
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 ￥51,208
￥101,989 total
includes taxes & fees
Nov 1 - Nov 2
Oceanside Kawama Villa R5
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

14. 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 ￥78,191
￥148,591 total
includes taxes & fees
Nov 1 - Nov 2
New Oceanside Paradise with Pool and Waterfront Views!
A coastal area with clear water, a sandy beach, and a small island with buildings.

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

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥14,502
￥46,290 total
includes taxes & fees
Nov 1 - Nov 2
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

16. 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 ￥40,069
￥77,950 total
includes taxes & fees
Nov 1 - Nov 2
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A boat docked at a wooden pier with a thatched roof overhead, surrounded by palm trees and water.

17. Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Key Largo
9.6 out of 10, Exceptional, (131 reviews)
"We appreciated having our boat docked behind the house. The campground was well maintained."
United States
Barbara A K.
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

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

1. Key Largo Waterfront Studio | Canal & Ocean
Key Largo
9.4 out of 10, Exceptional, (13 reviews)
"Stayed here multiple times and will continue to stay here."
United States
Monica G.
1. Key Largo Waterfront Studio | Canal & Ocean
An aerial view of a resort with multiple buildings, a central pool area, and a beach.

19. 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, (63 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is ￥43,420
￥95,869 total
includes taxes & fees
Nov 2 - Nov 3
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A round table set for two with a view of the ocean and palm trees.

20. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
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

Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Great location to explore key largo. Room was huge over two floors. Easy check in and great amenities."
Charles 1-night trip
Posted 5 hours ago
Waterside Suites & Marina

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Vacation Homes information

Number of reviews
1,205
Accommodation
622 Vacation Homes
Lowest Price
￥46,290
Highest Price
￥149,649

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