Upper Matecumbe Key Vacation Rentals

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Vacation Rentals in Upper Matecumbe Key

Breezy Palms Resort
Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very Good, 329 reviews
"For those who enjoy boating jet skiing is amazing!!!"
The price is $167
$240 total
includes taxes & fees
Jun 3 - Jun 4
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
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
Manatee: Luxury Bungalow, 4 Bedrooms, Bay View | Beach/ocean view
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
Property grounds
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
Private beach, sun loungers, beach umbrellas, beach towels
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, 73 reviews
"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
VOTED BEST KEY LARGO VACATION RENTAL
Property grounds
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, 61 reviews
"Perfect for our family, very clean as well!"
VOTED BEST KEY LARGO VACATION RENTAL
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Property grounds
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
Beach | Beach nearby
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!
Property grounds
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
Outdoor pool, a heated pool
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 $225
$474 total
includes taxes & fees
Jun 4 - Jun 5
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Fridge, microwave, oven, stovetop
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 $181
$438 total
includes taxes & fees
Jun 17 - Jun 18
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Lady Blue Yacht in FL KEYS
Beach
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 $220
$365 total
includes taxes & fees
Jun 15 - Jun 16
Lady Blue Yacht in FL KEYS
Beautiful Escape In Paradise
Property grounds
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
Outdoor dining
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
Outdoor dining
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
A heated pool
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
Property grounds
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, 75 reviews
"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
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Beach
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
10.0 out of 10, Exceptional, 162 reviews
"This development is fun. Great stay. Second time in this property. Great location and unit. Property manager responsive. Will stay here again."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Key Largo Cottages
Beach/ocean view
Key Largo Cottages
2.5 star property
9.4 out of 10, Exceptional, 19 reviews
"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
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
Outdoor dining
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 $443
$878 total
includes taxes & fees
Jun 9 - Jun 10
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.

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

Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, 1,008 reviews
"This hotel was like paradise. So beautiful "
The price is $249
$348 total
includes taxes & fees
Jun 4 - Jun 5
Cheeca Lodge & Spa
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels
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 $259
$331 total
includes taxes & fees
Jun 3 - Jun 4
Chesapeake Beach Resort
Amara Cay Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, 1,238 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 $284
$375 total
includes taxes & fees
Jun 4 - Jun 5
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.

Everything you need to know about Upper Matecumbe Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upper Matecumbe Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upper Matecumbe Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upper Matecumbe Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Upper Matecumbe Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $167 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upper Matecumbe Key rentals

At Expedia, we put the best Upper Matecumbe Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upper Matecumbe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upper Matecumbe Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Matecumbe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Upper Matecumbe Key properties
Expedia verified reviews

Hawks Cay Resort

Hawks Cay Resort

5/5 Excellent
"Love it"
A verified traveler stayed at Hawks Cay Resort
Posted 1 day ago
Hawks Cay Resort