Upper Matecumbe Key Holiday Rentals

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Holiday Rentals in Upper Matecumbe Key

Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, 329 reviews
"Love it!"
The price is NZ$392
includes taxes & fees
3 Jun - 4 Jun
Breezy Palms Resort
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, 35 reviews
"My wife and I have been traveling to Islandmorada for many years and this place is what we have been searching for. Clean, quaint, all the amenities of a large restort withiut the corporation feel. Absolutely refreshing!"
The Islands of Islamorada
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, 315 reviews
"Absolutely beautiful! Cant wait to come back and stay here again."
Mangrove Marina and Resort Aqualodge Houseboats
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Amazing Ocean view at Ocean Pointe w/Heated Pool
9.6 out of 10, Exceptional, 9 reviews
"The condo was nicely decorated. The kitchen was well stocked with everything for cooking. The beds were comfortable and plenty of bath and beach towels. Bring your own necessities, tp, paper towels, shampoo, soap everything else was there! The pool and beach are fantastic! We enjoyed our stay and would definitely stay again!"
Amazing Ocean view at Ocean Pointe w/Heated Pool
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, 73 reviews
"Amazing spot. Will definitely be coming back! "
Island Bay Resort
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, 61 reviews
"Exactly the place we needed"
VOTED BEST KEY LARGO VACATION RENTAL
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, 118 reviews
"The home we stayed in was lovely, and the host could not have been more accommodating. The grounds are beautiful. We swam in the lagoon, in the pool, and in the Atlantic, and took nighttime walks out to the end of the jetty, where we could see distant lights across the water to the right and the left, and open ocean expanse between. When we turned to look back at the grounds, it was so beautifully illuminated it completed the magic. We have already booked two more visits."
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, 24 reviews
"House was just as described. It was in the perfect location with supermarket and restaurants nearby. The house was super clean and had everything we needed for a relaxing vacation. My husband and son enjoyed fishing from the jetty and my daughter enjoyed sunning by the pool. We also enjoyed snorkeling in the lagoon and the beach. We're so happy we found this treasure. Can't wait to visit again!"
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
10.0 out of 10, Exceptional, 138 reviews
"Very nice."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
9.8 out of 10, Exceptional, 179 reviews
"Our stay was amazing from start to finish. The condo was beautiful and complete with everything we needed. The pool was perfect and allowed for night swimming after long days of recommended activities. The whole experience was great and I was telling everyone back in WI that it needs to be added to their accommodation list. Quiet and close enough to some really great restaurants as well. Felt like home!"
The price is NZ$775
includes taxes & fees
4 Jun - 5 Jun
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.6 out of 10, Exceptional, 31 reviews
"Super cute tiny house! Perfect for our night there. Wish we had more time."
The price is NZ$737
includes taxes & fees
17 Jun - 18 Jun
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Lady Blue Yacht in FL KEYS
7.0 out of 10, Good, 4 reviews
"We loved the experience until we couldn't access the WiFi for the television. There were a couple of wet places in the forward bedroom and bed, dirty underwear and shorts were left in the washer. We loved it though!"
The price is NZ$602
includes taxes & fees
1 Jul - 2 Jul
Lady Blue Yacht in FL KEYS
Beautiful Escape In Paradise
7.0 out of 10, Good, 2 reviews
"It took us little longer to find out how things worked. Only thing is the toilet had no water the last day"
Beautiful Escape In Paradise
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, 235 reviews
"Clean and comfortable! We really enjoyed our stay."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
9.2 out of 10, Wonderful, 59 reviews
"Dated RV that fulfilled our needs as an older couple. The host was wonderful! The grounds were very nice and the location made it easy for us to visit all the Keys. We had never lived in an RV before and the pull outs were nice. It had a few issues due to age, but we improvised and went with the flow. Enjoy your island time."
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, 207 reviews
"The location of this property was ideal for everything we wanted to do (activities from Tavernier all the way down to Key West). Check in was seamless and, while there was never a need to contact the property manager, the communication from them was clear and timely. The pool, landscaping, and overall neighborhood were all lovely. Very resort-like. That said, we did take note of several maintenance issues. The kitchen chairs were wobbly (and some of the hardware was later found in a fake...
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, 75 reviews
"The property has all we needed, ii was clean and quiet. It was the perfect place for a weekend getaway. Also, the communication with the host was very easy. I highly recommend it."
Key Largo Relaxing Getaway
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
10.0 out of 10, Exceptional, 162 reviews
"This place was exactly what we needed to get everything ready for our son’s wedding. We loved the kitchen for all of the desserts we made. It was nice to be so close to the pool. There was so much space to spread out. It’s a wonderful place to stay."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Key Largo Cottages
2.5 star property
9.4 out of 10, Exceptional, 18 reviews
"My daughter and I stayed here for a weekend. Had a fabulous time! Everyone was very nice and helpful. We went out in a canoe and used the snorkeling equipment. "
Key Largo Cottages
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
9.8 out of 10, Exceptional, 149 reviews
"Great Place to stay. Spacious and very clean."
The price is NZ$1,435
includes taxes & fees
9 Jun - 10 Jun
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
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See all available properties in Upper Matecumbe Key
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.

Other types of properties in Upper Matecumbe Key you may be interested in

Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, 1,005 reviews
"Lovely experience. A place we will come back to visit. "
The price is NZ$568
includes taxes & fees
10 Jun - 11 Jun
Cheeca Lodge & Spa
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, 1,333 reviews
"We really enjoyed it, staff was very nice and property was nice and clean. It has 2 pools and beach access. We would definitely come back!"
The price is NZ$494
includes taxes & fees
27 Jun - 28 Jun
Chesapeake Beach Resort
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, 1,237 reviews
"They are under new management and have made some nice changes. Beach towels are now by the pool, metal water bottles are given at check in and water stations are available to refill them. Free shuttle service is offered within a range. We used it every night to take us to dinner. Lunch at the pool bar is very good."
The price is NZ$587
includes taxes & fees
13 Jun - 14 Jun
Amara Cay 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upper Matecumbe Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upper Matecumbe Key. 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 Upper Matecumbe Key. 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 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 holiday 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 Upper Matecumbe Key short-term rentals, that won’t be hard to do.

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