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
8.8 out of 10, Excellent, (723 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is CA $128
CA $217 total
includes taxes & fees
Aug 10 - Aug 11
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 $2,257
CA $2,859 total
includes taxes & fees
Aug 15 - Aug 16
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, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is CA $149
CA $364 total
includes taxes & fees
Aug 11 - Aug 12
Treasure Harbor

4. Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (26 reviews)
"We had a great experience. Loved watching the sunset from the top deck. Great to cruise around in the electric catamaran. Kelly’s recommendations were great. We found the sand bar and the Dive restaurant at Mangrove Marina was fun with the live music."
United States
Carrie S.
The price is CA $370
CA $593 total
includes taxes & fees
Aug 10 - Aug 11
Island Sanctuary Islamorada

5. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (75 reviews)
"Convenient, affordable, pet friendly, "
United States
mark e.
The price is CA $157
CA $412 total
includes taxes & fees
Aug 12 - Aug 13
Paradise in Key Largo, FL

6. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
The price is CA $357
CA $402 total
includes taxes & fees
Aug 10 - Aug 11
Island Bay Resort

7. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (35 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is CA $127
CA $439 total
includes taxes & fees
Aug 30 - Aug 31
Florida Keys Getaway - Slps 4 - Ocean View

8. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 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 $188
CA $487 total
includes taxes & fees
Aug 10 - Aug 11
Amazing Ocean view condo

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

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 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 $138
CA $414 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is CA $263
CA $617 total
includes taxes & fees
Aug 10 - Aug 11
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

11. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (39 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is CA $158
CA $519 total
includes taxes & fees
Aug 11 - Aug 12
Charming Home in Key Largo

12. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (32 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
The price is CA $209
CA $707 total
includes taxes & fees
Aug 17 - Aug 18
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

13. 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, (49 reviews)
"This was the perfect little home away from home! The house was perfectly clean and nice and cool! The AC in the bedroom was fantastic and kept the room a perfect temperature for sleeping. In addition the bed was super comfortable! We had a great time in the campground and were so excited about the kayaks available for our use. We have already recommended this house and the campground to our friends and family and can’t wait to come and stay again soon!"
United States
Carrie D.
The price is CA $89
CA $384 total
includes taxes & fees
Aug 24 - Aug 25
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

14. 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)
"Loved the beach and pool."
United States
Haley P.
The price is CA $238
CA $625 total
includes taxes & fees
Aug 24 - Aug 25
Lazy Daze Double King Suite Ocean Pointe 2310

15. Coastal Joy 3412 Ocean Pointe King & Queen

Coastal Joy 3412 Ocean Pointe King & Queen
Tavernier
9.4 out of 10, Exceptional, (3 reviews)
"We had a perfect vacation. The unit and property were exactly as described but the photos and description don’t do it justice. The view is amazing, the condo is perfectly decorated, so comfortable and well stocked. We loved playing pickle ball and relaxing at the pool. Five stars!!"
United States
Jason & Kirsten C.
The price is CA $216
CA $598 total
includes taxes & fees
Sep 8 - Sep 9
Coastal Joy 3412 Ocean Pointe King & Queen

16. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
3212 Across from Pool * King & Queen/Twin Bunk Bed

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 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 $272
CA $628 total
includes taxes & fees
Aug 23 - Aug 24
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

18. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is CA $238
CA $629 total
includes taxes & fees
Sep 8 - Sep 9
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

19. Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Great view, love the pool and dock areas."
United States
Luke O.
The price is CA $238
CA $629 total
includes taxes & fees
Sep 8 - Sep 9
Nauti Hideaway Ocean Pointe 2314

20. 2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
The price is CA $225
CA $522 total
includes taxes & fees
Aug 17 - Aug 18
2BR Condo w/ Ocean View, Pool & Tropical Setting
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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