Photo by Cameron Abbott
Upper Matecumbe Key Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Upper Matecumbe Key vacation rentals
Aparthotel in Matecumbe
Breezy Palms Resort8.8 out of 10, Excellent, (600)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
Lisa
The price is P8,992
P13,165 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa in Matecumbe
The Islands of Islamorada9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
Dixania
The price is P35,824
P43,544 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Houseboat in Islamorada
Treasure Harbor9.0 out of 10, Wonderful, (120)
"Great spot! Will be back someday hopefully. "
Diane
The price is P74,074
P83,333 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Aparthotel in Tavernier
Island Bay Resort10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
Jacob
The price is P24,914
P28,028 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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.
Find vacation rentals that suit your style
Aparthotels
Villas
Save an average of 15% on thousands of hotels when you're signed in
Top Upper Matecumbe Key Hotel Reviews
Casa Morada
10/10 Excellent
Find out more about Upper Matecumbe Key
Search for holiday rentals in Upper Matecumbe Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Upper Matecumbe Key using one of the methods below:
- View our selection of featured holiday rentals in Upper Matecumbe Key
- Use the map to find apartments and other holiday homes in the Upper Matecumbe Key neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Upper Matecumbe Key while they last
Look no further and take a look at our great range of rental properties in Upper Matecumbe Key!
Explore a world of travel with Expedia
- Vacation Homes in Upper Matecumbe Key
- Apartments in Upper Matecumbe Key
- Cottages in Upper Matecumbe Key
- Resorts in Upper Matecumbe Key
- Villas in Upper Matecumbe Key
- Motels in Upper Matecumbe Key
- Houseboats in Upper Matecumbe Key
- Aparthotels in Upper Matecumbe Key
- Guest Houses in Upper Matecumbe Key
- Lodges in Upper Matecumbe Key
- Condo Resorts in Upper Matecumbe Key
- Condo Rentals in Upper Matecumbe Key
