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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
10.0 out of 10, Exceptional, (5 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is ￥26,863
￥69,805 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥17,066
￥57,677 total
includes taxes & fees
Oct 20 - Oct 21
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
9.4 out of 10, Exceptional, (53 reviews)
"We had a nice stay"
United States
Kevin M.
The price is ￥13,274
￥46,893 total
includes taxes & fees
Oct 31 - Nov 1
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A two-story building with a pool, a boat dock, and a table set for dining.

4. 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 ￥57,306
￥144,053 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront / Ocean Access Canal / Kamp Key / Homes
A bedroom with a large bed, a desk, and a chair, a mirror, and decorative wall art.

5. 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 ￥47,615
￥71,326 total
includes taxes & fees
Oct 21 - Oct 22
Serenity Bungalow at Largo Resort
A beach with a wooden structure and a signpost indicating directions to various locations.

6. 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 ￥41,283
￥101,158 total
includes taxes & fees
Oct 25 - Oct 26
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

7. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is ￥55,465
￥127,443 total
includes taxes & fees
Oct 26 - Oct 27
Oceanside Retreat w/Rooftop, Pool & Kayaks
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

8. 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 ￥41,480
￥89,490 total
includes taxes & fees
Oct 20 - Oct 21
Key Largo Kawama Villa L1, 3/3
A coastal residential area with modern buildings, a marina, and a clear view of the ocean.

9. 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.
4. Cozy Key Largo Waterfront Studio | Dive
An aerial view of a coastal resort with modern buildings, a central pool area, and clear turquoise waters.

10. Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Key Largo
7.0 out of 10, Good, (2 reviews)
"Fantastic property that was even better than advertised. I would definitely stay here again."
United States
John D.
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

11. 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 ￥47,248
￥86,892 total
includes taxes & fees
Nov 2 - Nov 3
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

12. 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 a large island, wooden ceiling, and a view of the pool.

13. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (74 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is ￥43,653
￥124,129 total
includes taxes & fees
Nov 16 - Nov 17
Sunrise Escape - Ocean Front Villa - Sleeps 10
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

14. Tranquility Bungalow at Largo Resort

Tranquility Bungalow at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (8 reviews)
"Very Zen atmosphere. Alex and the rest of the staff very friendly and welcoming. "
United States
Becky M.
The price is ￥47,615
￥71,800 total
includes taxes & fees
Oct 21 - Oct 22
Tranquility Bungalow at Largo Resort
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, and a woven pendant light.

15. Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp

Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp
Key Largo
10.0 out of 10, Exceptional, (16 reviews)
"Very clean place. Would stay again!"
United States
Carmen W.
Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp
A beach setting with a thatched umbrella, a small round table, and two chairs.

16. Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.4 out of 10, Exceptional, (136 reviews)
"Great villa!"
United States
Georgi T.
The price is ￥48,947
￥99,137 total
includes taxes & fees
Oct 20 - Oct 21
Key largo Kawama Villa N2
A wooden deck with yellow chairs, a pool, and a building with a covered area.

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 ￥19,436
￥53,826 total
includes taxes & fees
Oct 27 - Oct 28
Key Largo Tiny House, Marina, Beach + Pool Access
A wooden deck with lounge chairs, a pool, and a dock with boats.

18. 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 ￥20,701
￥56,197 total
includes taxes & fees
Nov 17 - Nov 18
Waterfront Tiny House w Pool, Beach, and Boat Dock
BBQ charcoal grills and tikies by the ocean

19. 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.
Oceanside Kawama Villa R5
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.
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.
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Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"Beautiful resort"
Patricia 2-night trip
Posted 1 hour ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Vacation Homes information

Number of reviews
985
Accommodation
622 Vacation Homes
Lowest Price
￥46,893
Highest Price
￥144,053

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