Upper Matecumbe Key Holiday Rentals from €183: Search Short-Term Rentals

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Holiday Rentals in Upper Matecumbe Key

"Beautiful views "

includes taxes & fees

10 Dec - 11 Dec

2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

"We loved the entire experiences; especially the amenities on site (kayaks, paddle boards, swimming-pool & ocean, food & bar) and Emmanuel (person responsible kayaks and paddle boards)."

includes taxes & fees

1 Dec - 2 Dec

Manatee: Luxury Bungalow, 4 Bedrooms, Bay View | Beach/ocean view

"We normally stay in hotel rooms when we travel, so we thought it would be fun to try a house boat when I saw the option. We had all the comforts that a hotel provides, but with a way cooler atmosphere. Our only disappointment it that we didn't stay long enough to try the pool and restaurant. Good experience. We'd stay again."

"Superb apartment. Amazing view. Nice bright kitchen / lounge. Well stocked. Lots of towels. Nice big pool and hot tub. Had a great time. "

Private beach, sun-loungers, beach umbrellas, beach towels

"Great experience!! Inn keepers and staff were very warm and friendly. Grounds are maintained perfectly great stay!!"

"5 of us really enjoyed our stay. Norman provided great information to enjoy using their bikes, face masks 7 snorkels, etc. Best part was snorkeling in the private "swimming hole" lagoon, with beach stocked with tropical fish.' We all want to return "

"We were staying during Hurricane milton. We had questions and they were answered almost instantly. This property is clean and nice ammenities. I will definitely stay here next time im in the keys. Highlyreccommend"

"This tiny home was AMAZING! We stayed here for a night on our way back from key west and it was the perfect place. The tiny home was super clean and had everything we needed. The beds were incredibly comfortable in both the loft upstairs and in the bedroom. Bathrooms were awesome as well. The campground was awesome and was very walkable, we didn’t use the pool or the beach access but both were close walking distance. Would definitely stay here again! There is a publix right outside of the...

includes taxes & fees

10 Dec - 11 Dec

"Property owner was exceptional to deal with and the property was very clean and cozy! The home had all the comforts of home. Enjoyed the pool, lagoon and my husband loved fishing off the jetty !! "

" We had a great time in your wonderful condo! It was amazingly quiet outside and the views were awesome! My daughter loved the raccoons. "

Beach nearby, sun-loungers, beach towels

"Father and Son fishing trip - great locations, property described just as it was, and a great complex. Would highly recommend. "

"Great location to get to everywhere we needed to in Key Largo!"

"We enjoyed our stay from beginning to end. The checking and check out was very smooth. Thank you so much!"

includes taxes & fees

26 Nov - 27 Nov

"The place was clean; everything worked as it should. It was in close proximity to a bathhouse and laundry service also. Nice, quiet community. Would definitely stay here again. Host was super and great about communicating despite the fact that we had a glitch on our end from not receiving our messages! Jeff took it all in stride and made sure we were taken care of!!"

"This house was perfect for our families (4 adults and 3 toddlers). It was very relaxing, tons of space, and in a great location within walking distance to the shoreline. There was a playground, swimming pool, and a lagoon right outside our back door! Everything was beautiful and the host was very quick to respond to any questions we had. Definitely would recommend this property! "

"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."

"Evacuating from Milton. Booking was easy and the place was a safe harbor."

includes taxes & fees

11 Dec - 12 Dec

"This was a fantastic property for two couples looking for a long weekend getaway. The location was fantastic - easy drive to Marathon, walking distance to Hawks Cay’s public restaurant and marina, private access to the canal. The private pool was big enough for four adults to cool off from the Florida sun and humidity. A great stay!"

"The condo was perfect for our quick getaway. Clean, modern, comfortable and exactly as pictured. Breathtaking views from the balcony. The pool and other amenities were just lovely and well maintained. Jorge, the owner, was so accommodating and quick to respond to my questions. We would come back again for sure."

"Condo was in perfect location with respect to getting to various areas of Key Largo and you can’t beat the short walk to the jetty to see beautiful sunsets. Condo had everything we needed for our stay there. This is our 2nd time staying at this particular unit and we’ll be back! "

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

"The views were amazing and the grounds were clean and the staff was friendly and tentative."

includes taxes & fees

25 Nov - 26 Nov

"My family truly enjoyed this resort. Extremely satisfied. We are your customers from now on. Thank you. "

includes taxes & fees

2 Dec - 3 Dec

Private beach, white sand, sun-loungers, beach towels

"The Staff was very accommodating. The room was clean and equipped with a microwave, refrigerator, and very comfortable Robes. We loved the view and the peacefulness."

includes taxes & fees

8 Dec - 9 Dec

Find out more about Upper Matecumbe Key

Everything you need to know about Upper Matecumbe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upper Matecumbe Key holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Matecumbe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Matecumbe Key holiday rentals we have selected for you start as low as €183 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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

5/5 Excellent

"From check in to check out the staff were amazing. The rooms were very clean and comfortable. The pool and lounging areas were even better than expected. My family is looking forward to book here again!"

A verified traveller stayed at Holiday Inn Key Largo, an IHG Hotel

Posted 1 day ago

Baker's Cay Resort Key Largo, Curio Collection by Hilton

5/5 Excellent

"Everything was right there, the beach. Dinning, and recreation. The service was impeccable. The Coconut wing room offers a spacious layout with a contemporary design, featuring soft neutral tones and sleek furnishings. You enjoy a panoramic beach views from the floor-to-ceiling windows,"

A verified traveller stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton

Posted 2 days ago

5/5 Excellent

"The girls hosting the properties were fun patient and very eager to serve our every request making our stay very pleasant. Andrea made our day upgrading us to an Oceanfront suite with a kitchenette. That impressed us the most. We will definitely make this beautiful place Our go to when we just have to get away from it all. The complementary kayaks, bikes, and paddle boards made us enjoy the properties even more. We would definitely recommend this to somebody visiting the keys for the first time. The location allowed us to visit the keys even better. The reasonable price gave us a good bang for our buck. We’re definitely going to return to this beautiful property with the magnificent sunsets."

A verified traveller stayed at Lime Tree Bay Resort

Posted 2 days ago

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Holiday Rentals in Upper Matecumbe Key

Check Upper Matecumbe Key holiday rental availability

Holiday Rentals in Upper Matecumbe Key

Breezy Palms Resort

The Islands of Islamorada

Mangrove Marina and Resort Aqualodge Houseboats

Amazing Ocean view at Ocean Pointe w/Heated Pool

Island Bay Resort

VOTED BEST KEY LARGO VACATION RENTAL

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

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

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

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

Beautiful Escape In Paradise

Lady Blue Yacht in FL KEYS

Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio

Villa Largo Island Retreat

Key Largo Cottages

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys

FALL'24 Sell-off Deals! Prime OCEANFRONT 1300sf LUX Condo-All Amenities of Home!

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

Cheeca Lodge & Spa

Amara Cay Resort

Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Recent reviews of Upper Matecumbe Key properties

Holiday Inn Key Largo, an IHG Hotel

Cheeca Lodge & Spa

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Lime Tree Bay Resort

Marina Del Mar Resort and Marina

Hadley Resort and Marina

Amara Cay Resort

Hawks Cay Resort

Chesapeake Beach Resort