Photo by Cameron Abbott

Upper Matecumbe Key hotel rooms a the Hersha Hospitality

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Upper Matecumbe Key Hersha Hospitality

Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1002)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
The price is P25,885
P33,084 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Islander Resort
Restaurant
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (401)
"Beautiful stay!!!"
United States
Lakyne
The price is P16,912
P22,990 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Bayside Villas by Islander Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Front desk help were Amazing, everyone working there were very friendly. Clean room, Super great breakfast, which is free and sitting outside to enjoy the beautiful scenery💝"
Noemy 1-night trip
Posted 2 days ago
Chesapeake Beach Resort

Explore a world of travel with Expedia