Upper Matecumbe Key Vacation Rentals

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Vacation Rentals in Upper Matecumbe Key

Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, (329)
"For those who enjoy boating jet skiing is amazing!!!"
The price is CA $223
CA $321 total
includes taxes & fees
Jun 9 - Jun 10
Breezy Palms Resort
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, (35)
"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)
"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)
"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
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (62)
"Perfect for our family, very clean as well!"
VOTED BEST KEY LARGO VACATION RENTAL
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, (73)
"What a wonderful, little tucked away gem!! We had such a great time here, the property is spotless and beautiful, the rooms were perfect in size and beautifully decorated, and the couple who run the property make you feel so welcome and like your family. We rarely left the property, it was so relaxing to sit on the beach, or take the kayaks or paddle boards out into the water, we even saw, sharks and manatees and got to swim with them right at the resort. We will definitely go back!"
Island Bay Resort
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (25)
"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)
"Very nice."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, (118)
"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
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
9.8 out of 10, Exceptional, (180)
"Very nice view. Convenient. Low water pressure. Not sure if was an overall property issue or just unit. But not a reason for not recommending. Try Chef Michael’s restaurant. Best seafood meal we have had in US and comparable to our favorite place in Sardinia Italy!"
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, (236)
"The place was fantastic. Balcony is very small, but not much can be done about that."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Lady Blue Yacht in FL KEYS
7.0 out of 10, Good, (4)
"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 CA $300
CA $499 total
includes taxes & fees
Jun 19 - Jun 20
Lady Blue Yacht in FL KEYS
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.6 out of 10, Exceptional, (32)
"Super cute tiny house! Perfect for our night there. Wish we had more time."
The price is CA $268
CA $623 total
includes taxes & fees
Jun 17 - Jun 18
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Beautiful Escape In Paradise
7.0 out of 10, Good, (2)
"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
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
9.2 out of 10, Wonderful, (59)
"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
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
9.8 out of 10, Exceptional, (149)
"Great Place to stay. Spacious and very clean."
The price is CA $604
CA $1,189 total
includes taxes & fees
Jun 9 - Jun 10
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, (207)
"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
UPSCALE KEY LARGO VILLA L1, MARINA, 2POOLS,SALTWATER LAGOON,TENNIS,BIKES,KAYAKS
9.4 out of 10, Exceptional, (200)
"House was wonderful..love the set up inside, thr decks and the ability to walk to the point!"
UPSCALE KEY LARGO VILLA L1, MARINA, 2POOLS,SALTWATER LAGOON,TENNIS,BIKES,KAYAKS
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, (75)
"Everything was great. We just didnt realize we would be staying in a modified camper. Communication with the owner was excellent."
Key Largo Relaxing Getaway
Key Largo Cottages
2.5 star property
9.4 out of 10, Exceptional, (19)
"Hotel is a hidden gem. Location and amenities are great. People working there couldn’t be more nice and attentive. Very very clean room, bathroom was outdated but that is the bast majority of hotels in the keys unless you want to pay a outrageous rate. I will definitely come back"
Key Largo Cottages
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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.

Upper Matecumbe Key Vacation Rental Travel Info

Vacation rentals
6
Popular accommodation
Upper Matecumbe Key private vacation homes
International airport
Key West, FL (EYW-Key West Intl.)

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

Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1337)
"Perfect stay! Beautiful location and property! "
The price is CA $318
CA $412 total
includes taxes & fees
Jun 20 - Jun 21
Chesapeake Beach Resort
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1008)
"LOVED our stay at Cheeca. We stayed in the main building this time and I can't recommend enough. The rooms were large and our children LOVED the outdoor bath/hot tub. The dining options on property are amazing as is the staff. Five stars and can't wait to go back!"
The price is CA $312
CA $443 total
includes taxes & fees
Jun 10 - Jun 11
Cheeca Lodge & Spa
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1241)
"We had the most relaxing time and the resort is in the best location to food and experiences! Access to La Siesta is a plus. We went during the work week, which made it a lot less crowded. I would absolutely recommend staying here to anyone!"
The price is CA $383
CA $507 total
includes taxes & fees
Jun 6 - Jun 7
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 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.

Recent reviews of Upper Matecumbe Key properties
Expedia verified reviews