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

Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $98
CA $183 total
includes taxes & fees
Nov 11 - Nov 12
Breezy Palms Resort

2. Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,287
CA $2,768 total
includes taxes & fees
Nov 14 - Nov 15
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

3. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (182 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is CA $144
CA $360 total
includes taxes & fees
Nov 9 - Nov 10
Treasure Harbor

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is CA $183
CA $519 total
includes taxes & fees
Nov 16 - Nov 17
Florida Keys Getaway - Slps 4 - Ocean View

5. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is CA $191
CA $471 total
includes taxes & fees
Nov 15 - Nov 16
Amazing Ocean view condo

6. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $184
CA $520 total
includes taxes & fees
Nov 19 - Nov 20
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

7. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is CA $177
CA $511 total
includes taxes & fees
Nov 15 - Nov 16
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

8. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is CA $140
CA $400 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

9. Flamingo Flats | Marina View | Ocean Pointe 5306

Flamingo Flats | Marina View | Ocean Pointe 5306
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is CA $227
CA $587 total
includes taxes & fees
Nov 14 - Nov 15
Flamingo Flats | Marina View | Ocean Pointe 5306

10. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
The price is CA $267
CA $477 total
includes taxes & fees
Nov 11 - Nov 12
Ocean Pointe Ocean View w/heated pool beach marina

11. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is CA $226
CA $596 total
includes taxes & fees
Nov 12 - Nov 13
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

12. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is CA $259
CA $622 total
includes taxes & fees
Nov 9 - Nov 10
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

13. Lazy Daze | Double King Suite | Ocean Pointe 2310

Lazy Daze | Double King Suite | Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
The price is CA $267
CA $644 total
includes taxes & fees
Dec 1 - Dec 2
Lazy Daze | Double King Suite | Ocean Pointe 2310

14. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is CA $252
CA $523 total
includes taxes & fees
Nov 14 - Nov 15
Ocean view condo with balcony/marina view

15. Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
Tavernier
9.4 out of 10, Exceptional, (3 reviews)
"Very clean. The view was amazing. Very comfortable beds. We are definitely coming back to this condo! "
United States
Jason U.
The price is CA $244
CA $616 total
includes taxes & fees
Nov 10 - Nov 11
Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

16. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Great stay"
United States
Blain R.
The price is CA $234
CA $606 total
includes taxes & fees
Dec 6 - Dec 7
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

17. Boho Chic | Steps to Pool | Ocean Pointe 3214

Boho Chic | Steps to Pool | Ocean Pointe 3214
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is CA $243
CA $616 total
includes taxes & fees
Dec 1 - Dec 2
Boho Chic | Steps to Pool | Ocean Pointe 3214

18. 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 CA $203
CA $555 total
includes taxes & fees
Nov 9 - Nov 10
Charming Home in Key Largo

19. Reel Key Largo | Next to Pool | Ocean Pointe 5209

Reel Key Largo | Next to Pool | Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
The price is CA $236
CA $608 total
includes taxes & fees
Nov 10 - Nov 11
Reel Key Largo | Next to Pool | Ocean Pointe 5209

20. Starfish Seas | Ocean View | Ocean Pointe 1302

Starfish Seas | Ocean View | Ocean Pointe 1302
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is CA $270
CA $647 total
includes taxes & fees
Nov 18 - Nov 19
Starfish Seas | Ocean View | Ocean Pointe 1302
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

Find out more about Upper Matecumbe Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upper Matecumbe Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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