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, (698 reviews)
"Enjoyed this place."
United States
Christopher
The price is CA $169
CA $264 total
includes taxes & fees
Jul 1 - Jul 2
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 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 $901
CA $1,091 total
includes taxes & fees
Jul 6 - Jul 7
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 $2,265
CA $2,871 total
includes taxes & fees
Jun 30 - Jul 1
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $191
CA $413 total
includes taxes & fees
Jun 29 - Jun 30
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 $1,296
CA $1,458 total
includes taxes & fees
Jun 29 - Jun 30
Premium Floating Bungalow by Stay Ombi

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (25 reviews)
"Great spot on the water for a unique experience! Kelly was very accommodating. "
United States
Lauren H.
The price is CA $372
CA $593 total
includes taxes & fees
Jun 19 - Jun 20
Island Sanctuary Islamorada

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 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 $288
CA $615 total
includes taxes & fees
Jun 22 - Jun 23
Ocean view condo with balcony/marina view

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (5 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is CA $230
CA $307 total
includes taxes & fees
Jun 22 - Jun 23
Caloosa Cove Resort by CoolVacay

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Matecumbe
10.0 out of 10, Exceptional, (10 reviews)
"Old Florida vibe with modern, clean condos. Perfect location to visit the Keys. "
United States
Beckie F.
The price is CA $354
CA $501 total
includes taxes & fees
Jun 25 - Jun 26
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

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 $264
CA $619 total
includes taxes & fees
Jun 30 - Jul 1
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Very nice small resort."
United States
Dan
The price is CA $409
CA $461 total
includes taxes & fees
Jun 25 - Jun 26
Island Bay Resort

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (31 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 $140
CA $461 total
includes taxes & fees
Jul 7 - Jul 8
Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Layton
8.8 out of 10, Excellent, (18 reviews)
"Beautiful location"
United States
Aaron M.
Florida Keys Getaway w/ Stunning Ocean Views

Coastal comfort in Ocean Pointe Suites.

Coastal comfort in Ocean Pointe Suites.
Tavernier
10.0 out of 10, Exceptional, (41 reviews)
"10 out of 10 wonderful place to stay highly recommend it definitely booking there again in the near future"
United States
Manuel
The price is CA $346
CA $927 total
includes taxes & fees
Jun 22 - Jun 23
Coastal comfort in Ocean Pointe Suites.

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is CA $274
CA $680 total
includes taxes & fees
Jul 14 - Jul 15
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is CA $347
CA $835 total
includes taxes & fees
Jun 22 - Jun 23
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
The price is CA $223
CA $613 total
includes taxes & fees
Jun 25 - Jun 26
Nauti Hideaway Ocean Pointe 2314

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (39 reviews)
"Beautifully decorated room with wonderful amenities. We appreciated the full kitchen, comfy beds and early morning ocean views. Kids loved the pool! "
Canada
Alicia
The price is CA $287
CA $640 total
includes taxes & fees
Jun 19 - Jun 20
Serene Oceanfront Keys Condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
The price is CA $280
CA $639 total
includes taxes & fees
Jun 30 - Jul 1
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Ocean View Corner Penthouse Ocean Pointe 5416

Ocean View Corner Penthouse Ocean Pointe 5416
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great place - love the location! "
United States
Ann C.
The price is CA $405
CA $856 total
includes taxes & fees
Jul 2 - Jul 3
Ocean View Corner Penthouse Ocean Pointe 5416
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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