Upper Matecumbe Key Holiday Rentals

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Our top choices for Upper Matecumbe Key holiday rentals

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (598)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is NZ$384
includes taxes & fees
11 Jan - 12 Jan 2026
Breezy Palms Resort

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is NZ$1,268
includes taxes & fees
5 Jan - 6 Jan 2026
The Islands of Islamorada
The price is NZ$4,303
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Suite @Islamorada With Pool Access - Twilight Suite
The price is NZ$2,171
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
The price is NZ$2,171
includes taxes & fees
4 Jan - 5 Jan 2026
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
The price is NZ$4,087
includes taxes & fees
4 Jan - 5 Jan 2026
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
The price is NZ$3,229
includes taxes & fees
4 Jan - 5 Jan 2026
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
The price is NZ$3,486
includes taxes & fees
4 Jan - 5 Jan 2026
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
The price is NZ$3,505
includes taxes & fees
4 Jan - 5 Jan 2026
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
The price is NZ$6,455
includes taxes & fees
4 Jan - 5 Jan 2026
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
The price is NZ$4,299
includes taxes & fees
4 Jan - 5 Jan 2026
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (118)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor

Mobile Home in Key Largo

Paradise in Key Largo, FL
9.6 out of 10, Exceptional, (63)
"Beautiful property. We uh, I very much enjoyed our stay highly recommend we will stay here again"
United States
George D.
Paradise in Key Largo, FL
2.0 star property
10.0 out of 10, Exceptional, (3)
"Set up of RV was very nice. Great location and amenities at the campground."
United States
Cynthia C.
The price is NZ$539
includes taxes & fees
7 Jan - 8 Jan 2026
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
3.5 star property
The price is NZ$2,427
includes taxes & fees
1 Jan - 2 Jan 2026
Premium Floating Bungalow by Stay Ombi

Mobile Home in Key Largo

Cozy place in Calusa Key Largo
9.4 out of 10, Exceptional, (12)
"Perfect weekend getaway location."
United States
Tex H.
The price is NZ$562
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy place in Calusa Key Largo

Houseboat in Tavernier

Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (13)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is NZ$722
includes taxes & fees
7 Jan - 8 Jan 2026
Island Sanctuary Islamorada
8.8 out of 10, Excellent, (19)
"Fun accommodation in Key Largo. Clean, good size, nice pool."
United States
James C.
The price is NZ$492
includes taxes & fees
6 Jan - 7 Jan 2026
RV by the Sea - Glamping in the Keys - Sleeps 6
9.8 out of 10, Exceptional, (41)
"The cleanliness, the availability, the comfort. Everything was perfect in fact. Vz are planning on contacting the owner and tomorrow maybe arrange another rental on that property. It was in the perfect spot walking distance to the pool. Everything was readily available. Everything that they advertised was actually above and beyond. Our expectations can't say enough. Good about it was a perfect vacation. Thank you"
United States
Steve V.
The price is NZ$533
includes taxes & fees
7 Jan - 8 Jan 2026
Paradise in Key Largo Florida 2
10.0 out of 10, Exceptional, (122)
"We enjoyed our stay!"
United States
Halley R.
The price is NZ$812
includes taxes & fees
11 Jan - 12 Jan 2026
Modern and Coastal Ocean Pointe 2307
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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Top Upper Matecumbe Key Hotel Reviews

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, 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 NZ$384 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.