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, (624 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 $235
CA $335 total
includes taxes & fees
Mar 25 - Mar 26
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (71 reviews)
"Beautiful accommodations and location, very clean, many activities available at resort"
United States
Janet
The price is CA $1,226
CA $1,455 total
includes taxes & fees
Mar 3 - Mar 4
The Islands of Islamorada

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

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is CA $2,590
CA $3,282 total
includes taxes & fees
Mar 7 - Mar 8
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is CA $1,364
CA $1,728 total
includes taxes & fees
Mar 7 - Mar 8
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 $1,364
CA $1,728 total
includes taxes & fees
Mar 7 - Mar 8
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 $2,046
CA $2,592 total
includes taxes & fees
Mar 7 - Mar 8
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 $2,208
CA $2,798 total
includes taxes & fees
Mar 7 - Mar 8
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 $2,221
CA $2,815 total
includes taxes & fees
Mar 7 - Mar 8
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is CA $2,725
CA $3,453 total
includes taxes & fees
Mar 7 - Mar 8
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 $2,728
CA $3,456 total
includes taxes & fees
Mar 7 - Mar 8
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 $4,092
CA $5,175 total
includes taxes & fees
Mar 7 - Mar 8
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, (136 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
The price is CA $269
CA $494 total
includes taxes & fees
Mar 3 - Mar 4
Treasure Harbor

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is CA $362
CA $580 total
includes taxes & fees
Mar 2 - Mar 3
Island Sanctuary Islamorada

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (66 reviews)
"Host was accommodating to our early arrival, responded promptly to communication, property met our expectations. I would recommend this property to anyone wanting a dive weekend or longer."
United States
Rick T.
The price is CA $209
CA $472 total
includes taxes & fees
Mar 12 - Mar 13
Paradise in Key Largo, FL

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 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 $277
CA $593 total
includes taxes & fees
Mar 30 - Mar 31
Amazing Ocean view condo

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, (23 reviews)
"Good stay"
Netherlands
Anna d.
The price is CA $139
CA $428 total
includes taxes & fees
Mar 5 - Mar 6
RV by the Sea - Glamping in the Keys - Sleeps 6

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $382
CA $754 total
includes taxes & fees
Mar 10 - Mar 11
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (31 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is CA $239
CA $614 total
includes taxes & fees
Mar 29 - Mar 30
Charming Home in Key Largo

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, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is CA $236
CA $622 total
includes taxes & fees
Mar 3 - Mar 4
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

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 $258
CA $650 total
includes taxes & fees
Mar 4 - Mar 5
3212 Across from Pool * King & Queen/Twin Bunk Bed
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.