Search Holiday Rentals in Upper Matecumbe Key

  • 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

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 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 17.107.350 ₫
20.696.603 ₫ total
includes taxes & fees
11 Jun - 12 Jun
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (687 reviews)
"Very clean, spacious, well located."
United Kingdom
Teresa
The price is 3.404.072 ₫
5.194.580 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Breezy Palms Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (156 reviews)
"Beautiful accommodations. Friendly staff. Dallas made it feel like home. Great scenery! Daily viewing of dolphin and manatee! We will definitely be back !"
United States
Cheryl
The price is 3.349.303 ₫
7.470.763 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Treasure Harbor

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (3 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
Caloosa Cove Resort by CoolVacay

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (170 reviews)
"Very nice small resort."
United States
Dan
The price is 7.700.939 ₫
8.663.557 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Island Bay Resort

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 24.379.948 ₫
27.427.441 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Premium Floating Bungalow by Stay Ombi

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
The price is 14.166.078 ₫
27.532.484 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Florida Keys Getaway w/ Stunning Ocean Views
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