Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is CA $790
CA $964 total
includes taxes & fees
May 14 - May 15
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (671 reviews)
"Place was nicer inside than out. Great location."
United States
Marcos
The price is CA $173
CA $265 total
includes taxes & fees
May 18 - May 19
Breezy Palms Resort

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,214
CA $2,806 total
includes taxes & fees
May 16 - May 17
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Sunset Access + Boat Basin | Walkable Islamorada

Sunset Access + Boat Basin | Walkable Islamorada
Matecumbe
10.0 out of 10, Exceptional, (45 reviews)
"Great location, stay, and nice to have the boat slip in the back yard. Will book again."
United States
Orion T.
The price is CA $323
CA $725 total
includes taxes & fees
Jun 1 - Jun 2
Sunset Access + Boat Basin | Walkable Islamorada

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $171
CA $385 total
includes taxes & fees
May 12 - May 13
Treasure Harbor

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)
The price is CA $1,337
CA $1,504 total
includes taxes & fees
May 11 - May 12
Premium Floating Bungalow by Stay Ombi

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
Key Largo
8.6 out of 10, Excellent, (92 reviews)
"Great stay for the price"
United States
William B J.
The price is CA $152
CA $445 total
includes taxes & fees
May 27 - May 28
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
The price is CA $392
CA $441 total
includes taxes & fees
Jun 10 - Jun 11
Island Bay Resort

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (127 reviews)
"Great place, great view, great hosts. No complaints about a thing. Publix is 2 minutes away, the campground is peaceful, house was clean. There were 4 of us and we had plenty of room. Will do that again"
United States
Joe J.
The price is CA $298
CA $682 total
includes taxes & fees
May 27 - May 28
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180 reviews)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
The price is CA $416
CA $851 total
includes taxes & fees
May 11 - May 12
Oceanside Kawama Villa R5

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (66 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is CA $425
CA $893 total
includes taxes & fees
May 17 - May 18
Beautiful Kawama Townhouse

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (43 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
The price is CA $277
CA $594 total
includes taxes & fees
May 11 - May 12
Ocean view condo with balcony/marina view

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"My family and I had a great time. The place was very comfortable. Location was great and we enjoyed all the amenities. Great experience over all."
United States
Raul e.
The price is CA $465
CA $923 total
includes taxes & fees
May 14 - May 15
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

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, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
The price is CA $254
CA $647 total
includes taxes & fees
May 31 - Jun 1
3212 Across from Pool * King & Queen/Twin Bunk Bed

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (54 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveller
The price is CA $431
CA $894 total
includes taxes & fees
May 18 - May 19
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (95 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is CA $259
CA $450 total
includes taxes & fees
May 11 - May 12
Dazzling Ocean Pointe -OP-Main

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (240 reviews)
"Great place to stay"
United States
Llonda B.
The price is CA $376
CA $737 total
includes taxes & fees
May 30 - May 31
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Key Largo Ocean Shore Villa 3 with pool & boat slip

Key Largo Ocean Shore Villa 3 with pool & boat slip
Key Largo
9.8 out of 10, Exceptional, (135 reviews)
"Beautiful, clean stay in Key Largo with views of the inlet, and kayaks on site to explore from! The unit had everything my family needed and we loved our 3 nights here."
United States
Heather W.
The price is CA $442
CA $842 total
includes taxes & fees
May 13 - May 14
Key Largo Ocean Shore Villa 3 with pool & boat slip

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
The price is CA $250
CA $595 total
includes taxes & fees
May 14 - May 15
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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.