Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (666 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is CA $164
CA $256 total
includes taxes & fees
May 7 - May 8
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (74 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 $821
CA $999 total
includes taxes & fees
May 4 - May 5
The Islands of Islamorada

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,215
CA $2,802 total
includes taxes & fees
May 7 - May 8
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Hidden Gem Islamorada | 1st Floor

Hidden Gem Islamorada | 1st Floor
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 $361
CA $773 total
includes taxes & fees
May 25 - May 26
Hidden Gem Islamorada | 1st Floor

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (151 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $171
CA $385 total
includes taxes & fees
May 6 - May 7
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 $1,589
CA $1,788 total
includes taxes & fees
May 2 - May 3
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 $188
CA $488 total
includes taxes & fees
May 4 - May 5
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, (164 reviews)
"Very nice small resort."
United States
Dan
Island Bay Resort

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, (46 reviews)
"I really enjoyed our stay at the campsite. The home is right on the water with plenty of activities to do. Also the grocery store and places to eat are only a few minutes away. "
United States
Everett S.
The price is CA $146
CA $436 total
includes taxes & fees
May 19 - May 20
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

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, (239 reviews)
"Great place to stay"
United States
Llonda B.
The price is CA $246
CA $571 total
includes taxes & fees
May 1 - May 2
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
"Great for a short stay! "
United States
Anonymous traveller
The price is CA $158
CA $457 total
includes taxes & fees
May 4 - May 5
Cozy place in Calusa Key Largo

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 $591 total
includes taxes & fees
May 3 - May 4
Ocean view condo with balcony/marina view

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Everything was as described and we truly enjoyed our stay. We traveled with small children and the home was fit for them. It’s a true vacation place. I highly recommend staying! "
United States
keli p.
The price is CA $267
CA $613 total
includes taxes & fees
May 1 - May 2
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (94 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is CA $259
CA $450 total
includes taxes & fees
May 4 - May 5
Dazzling Ocean Pointe -OP-Main

Toes in the Sand - 2 Bedroom Condo Sleeps 4

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Tavernier
10.0 out of 10, Exceptional, (37 reviews)
"Property was amazing. It had everything you might need, close to the water, stores, entertainment, and parks. Hosts were responsive and made every effort to accommodate any our needs."
United States
Marlyn A.
The price is CA $158
CA $565 total
includes taxes & fees
May 21 - May 22
Toes in the Sand - 2 Bedroom Condo Sleeps 4

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (11 reviews)
"Set up of RV was very nice. Great location and amenities at the campground."
United States
Cynthia C.
The price is CA $217
CA $516 total
includes taxes & fees
May 4 - May 5
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.6 out of 10, Exceptional, (69 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is CA $154
CA $402 total
includes taxes & fees
May 4 - May 5
Paradise in Key Largo, FL

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!

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)
"The condo was spotless and beautifully decorated. The hosts are exceptionally thoughtful, leaving clear instructions on how to use / where to find items, and a welcome guide with information on local attractions and restaurants. I loved the attention to detail, such as placing nightlights in the bathrooms and beach chairs. The balcony is not large, but comfortably seats two people and offers an expansive view of the ocean. Ocean Pointe is a beautiful complex with a nice pool and beach. I...
United States
Andrea
The price is CA $254
CA $645 total
includes taxes & fees
May 3 - May 4
3212 Across from Pool * King & Queen/Twin Bunk Bed

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (133 reviews)
"The unit was clean and beautiful. The entire complex was very nice, too. We had everything needed to enjoy our stay."
United States
Rhonda D.
The price is CA $324
CA $738 total
includes taxes & fees
May 3 - May 4
Casa Largo
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.