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

Upper Matecumbe Key Holiday Rentals

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Our top choices for Upper Matecumbe Key holiday rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (725 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is NZ$224
includes taxes & fees
2 Sept - 3 Sept
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 NZ$3,361
includes taxes & fees
20 Aug - 21 Aug
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, (169 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 NZ$464
includes taxes & fees
16 Aug - 17 Aug
Treasure Harbor

4. 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 NZ$492
includes taxes & fees
16 Aug - 17 Aug
Island Bay Resort

5. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is NZ$1,582
includes taxes & fees
16 Aug - 17 Aug
Premium Floating Bungalow by Stay Ombi

6. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
The price is NZ$936
includes taxes & fees
9 Sept - 10 Sept
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

7. 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 NZ$720
includes taxes & fees
15 Aug - 16 Aug
Island Sanctuary Islamorada

8. 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 NZ$748
includes taxes & fees
31 Aug - 1 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

9. 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

10. 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 NZ$824
includes taxes & fees
17 Aug - 18 Aug
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

11. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is NZ$763
includes taxes & fees
25 Aug - 26 Aug
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

12. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is NZ$671
includes taxes & fees
27 Aug - 28 Aug
Ocean view condo with balcony/marina view

13. Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
Tavernier
9.6 out of 10, Exceptional, (89 reviews)
"Good location"
United States
Dimitri O.
The price is NZ$762
includes taxes & fees
23 Aug - 24 Aug
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

14. 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, (33 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 NZ$858
includes taxes & fees
17 Aug - 18 Aug
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

15. 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 NZ$761
includes taxes & fees
23 Aug - 24 Aug
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

16. 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 NZ$765
includes taxes & fees
17 Aug - 18 Aug
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

17. Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 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 NZ$765
includes taxes & fees
31 Aug - 1 Sept
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

18. Private 3-bedroom brand new apartment in Tavernier, Key Largo

Private 3-bedroom brand new apartment in Tavernier, Key Largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"The amenities and location were nice for being close to Key Largo. There is a small park that faces the Atlantic side which is a 1 minute walk from the apartment. "
United States
Kathleen A.
The price is NZ$945
includes taxes & fees
17 Aug - 18 Aug
Private 3-bedroom brand new apartment in Tavernier, Key Largo

19. Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.8 out of 10, Exceptional, (9 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
The price is NZ$739
includes taxes & fees
13 Sept - 14 Sept
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

20. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (36 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 NZ$513
includes taxes & fees
2 Sept - 3 Sept
Florida Keys Getaway - Slps 4 - Ocean View
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upper Matecumbe Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upper Matecumbe Key. 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 Upper Matecumbe Key. 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 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 holiday 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 Upper Matecumbe Key short-term rentals, that won’t be hard to do.

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