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, (616 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is CA $270
CA $374 total
includes taxes & fees
Feb 8 - Feb 9
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is CA $1,233
CA $1,462 total
includes taxes & fees
Feb 26 - Feb 27
The Islands of Islamorada

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is CA $1,368
CA $1,733 total
includes taxes & fees
Feb 14 - Feb 15
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
The price is CA $1,368
CA $1,733 total
includes taxes & fees
Feb 14 - Feb 15
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is CA $2,051
CA $2,599 total
includes taxes & fees
Feb 14 - Feb 15
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

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 $2,805 total
includes taxes & fees
Feb 14 - Feb 15
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is CA $2,226
CA $2,822 total
includes taxes & fees
Feb 14 - Feb 15
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is CA $2,597
CA $3,291 total
includes taxes & fees
Feb 14 - Feb 15
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is CA $2,732
CA $3,462 total
includes taxes & fees
Feb 14 - Feb 15
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is CA $2,735
CA $3,465 total
includes taxes & fees
Feb 14 - Feb 15
Charming Suite @Islamorada With Pool Access - Twilight Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is CA $4,103
CA $5,188 total
includes taxes & fees
Feb 14 - Feb 15
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (129 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
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, (1 review)
The price is CA $1,258
CA $1,415 total
includes taxes & fees
Feb 11 - Feb 12
Premium Floating Bungalow by Stay Ombi

RV by the Sea - Glamping in the Keys - Sleeps 6

RV by the Sea - Glamping in the Keys - Sleeps 6
Key Largo
9.0 out of 10, Wonderful, (21 reviews)
"The camper was clean and comfortable. The extras for the beach were great."
United States
SUSAN C.
The price is CA $118
CA $399 total
includes taxes & fees
Feb 8 - Feb 9
RV by the Sea - Glamping in the Keys - Sleeps 6

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (43 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is CA $302
CA $627 total
includes taxes & fees
Mar 1 - Mar 2
Amazing Ocean view condo

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, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is CA $301
CA $702 total
includes taxes & fees
Mar 4 - Mar 5
3212 Across from Pool * King & Queen/Twin Bunk Bed

Paradise in Key Largo Florida 2

Paradise in Key Largo Florida 2
Key Largo
9.8 out of 10, Exceptional, (41 reviews)
"The cleanliness, the availability, the comfort. Everything was perfect in fact. Vz are planning on contacting the owner and tomorrow maybe arrange another rental on that property. It was in the perfect spot walking distance to the pool. Everything was readily available. Everything that they advertised was actually above and beyond. Our expectations can't say enough. Good about it was a perfect vacation. Thank you"
United States
Steve V.
The price is CA $309
CA $599 total
includes taxes & fees
Mar 9 - Mar 10
Paradise in Key Largo Florida 2

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (20 reviews)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is CA $163
CA $484 total
includes taxes & fees
Feb 9 - Feb 10
Florida Keys Getaway - Slps 4 - Ocean View

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is CA $363
CA $582 total
includes taxes & fees
Feb 9 - Feb 10
Island Sanctuary Islamorada

Where the sea, sun, and sand are just outside your door!

Where the sea, sun, and sand are just outside your door!
Key Largo
9.6 out of 10, Exceptional, (31 reviews)
"Everything is as described. We brought our boat and used the marina. Our trailer fit on the property’s as well. "
United States
Jane O.
The price is CA $273
CA $537 total
includes taxes & fees
Feb 9 - Feb 10
Where the sea, sun, and sand are just outside your door!
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.