Upper Matecumbe Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upper Matecumbe Key holiday rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (675 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
The price is NZ$329
includes taxes & fees
27 May - 28 May
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is NZ$1,188
includes taxes & fees
17 May - 18 May
The Islands of Islamorada

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is NZ$3,388
includes taxes & fees
27 May - 28 May
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is NZ$593
includes taxes & fees
6 June - 7 June
Treasure Harbor

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"What a neat experience, wonderful boat, waking up on the water was beautiful! Kelly was cery responsive to anything we needed!"
United States
Leanne W.
The price is NZ$703
includes taxes & fees
17 May - 18 May
Island Sanctuary Islamorada

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$1,847
includes taxes & fees
20 May - 21 May
Premium Floating Bungalow by Stay Ombi

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
The price is NZ$542
includes taxes & fees
8 June - 9 June
Island Bay Resort

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$737
includes taxes & fees
10 June - 11 June
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is NZ$794
includes taxes & fees
3 June - 4 June
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (48 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is NZ$669
includes taxes & fees
21 May - 22 May
Amazing Ocean view condo

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (17 reviews)
"Perfect Stay."
United States
suhaela s.
The price is NZ$761
includes taxes & fees
25 May - 26 May
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
The price is NZ$905
includes taxes & fees
16 May - 17 May
3212 Across from Pool * King & Queen/Twin Bunk Bed

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (44 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
The price is NZ$723
includes taxes & fees
18 May - 19 May
Ocean view condo with balcony/marina view

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very good, (11 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
The price is NZ$547
includes taxes & fees
21 May - 22 May
OP-2 Ocean View w/heated pool beach marina

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
The price is NZ$730
includes taxes & fees
18 May - 19 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (135 reviews)
"The unit was clean and beautiful. The entire complex was very nice, too. We had everything needed to enjoy our stay."
United States
Rhonda D.
The price is NZ$889
includes taxes & fees
18 May - 19 May
Casa Largo

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (95 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is NZ$539
includes taxes & fees
17 May - 18 May
Dazzling Ocean Pointe -OP-Main

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.6 out of 10, Exceptional, (69 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is NZ$490
includes taxes & fees
28 May - 29 May
Paradise in Key Largo, FL

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"The unit was clean. The bed was comfortable. Everything worked well."
United States
William G.
The price is NZ$763
includes taxes & fees
9 June - 10 June
Blue Haven Key Largo | Ocean Pointe 1315

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is NZ$987
includes taxes & fees
22 May - 23 May
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
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.
Save an average of 15% on thousands of hotels when you're signed in

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$329 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.