Upper Matecumbe Key Holiday Rentals

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Holiday Rentals in Upper Matecumbe Key

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"nice warm pool, nice ocean views."
The price is AU$387
includes taxes & fees
10 Mar - 11 Mar
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (49)
"Lovely room with friendly staff. "
The price is AU$1,153
includes taxes & fees
2 Mar - 3 Mar
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is AU$812
includes taxes & fees
12 Feb - 13 Feb
Key Largo Cottages

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (45)
"We spent a week uch enjoyed our visit. It's a little dated but very clean and comfortable. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Island Bay Resort

2.5 star property
9.8 out of 10, Exceptional, (98)
"This boutique cottage-based resort is a gem. We found the owners/operators (Steve & Sue) to be gracious and super-friendly as they seek to accommodate their guests and keep everything looking picture-perfect. It's a bit of paradise!"
Island Bay Resort

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (49)
"Clean, quiet and comfortable. The only problem was the lockbox. It took us 1/2 hour to open because the button is worn down so bad. They should get a new one. It was so frustrating. Otherwise the time house was perfect"
The price is AU$788
includes taxes & fees
2 Mar - 3 Mar
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

9.0 out of 10, Wonderful, (28)
"The RV park is top notch. Many activities to keep kids busy and has laundry facilities, trash pickup - very well cared for. The RV we stayed in was roomy and fairly comfortable. It needs a little TLC and a bit more attention to detail in cleanliness. All in all, it waswonderful stay."
The price is AU$573
includes taxes & fees
11 Feb - 12 Feb
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

9.8 out of 10, Exceptional, (10)
"Really nice place, no surprises. Location was excellent and pictures and description very accurate. Unfortunately, the weather was not in our favor but can't control that! Would definitely stay here again."
The price is AU$746
includes taxes & fees
23 Feb - 24 Feb
Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (100)
"If you are looking for an easy place to stay near Pennekamp State Park, this is a great option. Our family of 5 (4 adults 16 year old) enjoyed the great views and convenient location. It's small but adequate and had everything we needed for a couple of nights! "
The price is AU$1,062
includes taxes & fees
19 Feb - 20 Feb
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Beautiful Escape In Paradise

8.0 out of 10, Very good, (3)
"Great location to get to everywhere we needed to in Key Largo!"
Beautiful Escape In Paradise

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

9.6 out of 10, Exceptional, (50)
"This lovely cottage was really clean and comfortable. Nice roomy patio. I would definitely recommend it."
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

Mangrove Marina and Resort Aqualodge Houseboats

3.0 star property
9.4 out of 10, Exceptional, (326)
"The staff is amazing and all their recommendations were on point "
Mangrove Marina and Resort Aqualodge Houseboats

RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!

9.6 out of 10, Exceptional, (173)
"You could not find a better place to sit and watch the sunrise. Dolphins and pelicans occasionally distract you from the dawn. Despite its great location and proximity to restaurants and activities, you really don't need to leave the living room (it was abnormally cold when we were there) or the porch to be entirely entertained. "
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (141)
"Best equipped condo ever, also nice firm mattresses. The only little glitch, was getting the keys out of the lock box. This could be replaced! We would love to stay here again!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

Cozy place in Calusa Key Largo

9.4 out of 10, Exceptional, (6)
"We enjoyed our time there it was very nice place. A really great rv park with a pool. And close to everything in Key largo "
The price is AU$534
includes taxes & fees
10 Feb - 11 Feb
Cozy place in Calusa Key Largo

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (182)
"Great place, great communications with host."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (73)
"We had a great time. The accommodations had everything we needed. We loved having access to kayaks and paddle boards. Great and safe area to walk and ride bikes. They had fire pits and a great rock peninsula area to view sunsets and sunrises. There was a marina with fishing opportunities leaving area marina. The only negatives were no working bikes and not a fourth bedroom. It really was 3 bedrooms with a den area with a couch that made a bed.Would go again! Norman, the property manager, was the...
VOTED BEST KEY LARGO VACATION RENTAL

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

9.8 out of 10, Exceptional, (22)
"Our family had an amazing trip to the Keys. We were able to drive to several different Islands in a short amount of time. Great restaurants around as well!"
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio

9.4 out of 10, Exceptional, (68)
"Property was excellent for camping. Recommend 10of10. "
Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio

Stunning Morning View w/ Boat Slip, Cove

10.0 out of 10, Exceptional, (31)
"We had a wonderful stay at your condo and didn't want to leave. Everything was clean and beautifully decorated. The outdoor area was so pleasant. Lots of room for two couples. Close to many great restaurants. Can't wait to come back!"
Stunning Morning View w/ Boat Slip, Cove
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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Other types of properties in Upper Matecumbe Key you may be interested in

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1215)
"supper friendly and professional staff! "
The price is AU$683
includes taxes & fees
11 Feb - 12 Feb
Amara Cay Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1032)
"Elijah (at front desk) and Renee (server for 34 years) provided excellent service! Renee even remembered me from previous stays. Thank you both for making my stay memorable!"
The price is AU$644
includes taxes & fees
23 Feb - 24 Feb
Cheeca Lodge & Spa

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1395)
"I enjoyed my stay. The breakfast was great and outdoor breakfast seating facing the ocean was a great way to start the day. Can’t beat the beach loungers scattered around the property."
The price is AU$605
includes taxes & fees
11 Feb - 12 Feb
Chesapeake Beach Resort
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.