Search Vacation 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
  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Upper Matecumbe Key vacation homes

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 ¥23,808
¥63,369 total
includes taxes & fees
Dec 1 - Dec 2
Little Peace of Haven

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is ¥17,543
¥56,084 total
includes taxes & fees
Nov 15 - Nov 16
Charming Home in Key Largo

3. Key Lime Cottage in Islamorada

Key Lime Cottage in Islamorada
Matecumbe
10.0 out of 10, Exceptional, (49 reviews)
"Cute little cottage perfect for a weekend getaway. Enjoyed pool area, convenient location on our road trip down the Keys!"
United States
Karen L.
The price is ¥37,546
¥68,818 total
includes taxes & fees
Nov 16 - Nov 17
Key Lime Cottage in Islamorada

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 ¥21,538
¥55,220 total
includes taxes & fees
Nov 18 - Nov 19
Key Largo Tiny House, Marina, Beach + Pool Access

5. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (77 reviews)
"Great place!"
United States
Jessica S.
The price is ¥41,312
¥122,646 total
includes taxes & fees
Nov 17 - Nov 18
Sunrise Escape - Ocean Front Villa - Sleeps 10

6. Waterfront 3BR Retreat: Pool, Spa & Kayaks

Waterfront 3BR Retreat: Pool, Spa & Kayaks
Key Largo
Waterfront 3BR Retreat: Pool, Spa & Kayaks

7. 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 ¥53,370
¥75,656 total
includes taxes & fees
Nov 17 - Nov 18
Serenity Bungalow at Largo Resort

8. 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 ¥54,219
¥102,289 total
includes taxes & fees
Nov 17 - Nov 18
Key largo Kawama Villa N2

9. 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

10. 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 ¥39,521
¥73,111 total
includes taxes & fees
Nov 17 - Nov 18
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

11. Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (138 reviews)
"Would definitely come back to the same place over and over again !!"
United States
madi a.
Casa Largo

12. 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.
Kawama G12 Upscale OceansideVilla with Marina 2/2

13. Walk to Beach: Florida Keys Gem w/ Ocean Views

Walk to Beach: Florida Keys Gem w/ Ocean Views
Layton
9.2 out of 10, Wonderful, (5 reviews)
"The location is pretty good and stay is better than what shown in image "
United States
Shanikumar G.
The price is ¥69,361
¥105,470 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Beach: Florida Keys Gem w/ Ocean Views

14. 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 ¥17,418
¥50,267 total
includes taxes & fees
Nov 17 - Nov 18
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

15. 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.
New Oceanside Paradise with Pool and Waterfront Views!

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

New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Key Largo
8.8 out of 10, Excellent, (3 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 ¥23,786
¥58,066 total
includes taxes & fees
Dec 1 - Dec 2
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina

17. Sunset Bay View Bungalow at Largo Resort

Sunset Bay View Bungalow at Largo Resort
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"We got everything we need, a relaxing place, great service, easy to find, restaurants all over the place and most important of all very clean and beautiful. We loved."
United States
Ricardo M.
The price is ¥53,370
¥75,338 total
includes taxes & fees
Nov 15 - Nov 16
Sunset Bay View Bungalow at Largo Resort

18. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"Perfect rental, can’t say enough about it. The host was fantastic. Would definitely stay here again."
United States
Tammy C.
The price is ¥29,839
¥73,874 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

19. 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.
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

20. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Great property. Highly recommend."
United States
Karl B.
The price is ¥79,155
¥150,098 total
includes taxes & fees
Nov 16 - Nov 17
Oceanside Retreat w/Rooftop, Pool & Kayaks
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.

Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top reviews in Upper Matecumbe Key

Explore a world of travel with Expedia