Photo by Cameron Abbott

Find 5 Star Hotels in Upper Matecumbe Key, FL from $282

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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Compare Upper Matecumbe Key 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1263)
"It was absolutely beautiful and the staff was always super nice!"
United States
Mary
$317 nightly
The price is $357
Dec 17 - Dec 18
Total with taxes and fees
Cheeca Lodge & Spa
Outdoor pool
Condo in the Keys

Condo in the Keys

5.0 star property
Tavernier
8.0 out of 10, Very Good, (13)
"Love the location "
United States
Angela
Condo in the Keys
Design Villa, Canal View | Balcony
Waterfront House with Boat Dock

Waterfront House with Boat Dock

5.0 star property
Hammer Point
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
United States
Matthew
Waterfront House with Boat Dock
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upper Matecumbe Key.
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
$385 nightly
The price is $432 total per night from Dec 15 to Dec 16
$432 total
Dec 15 - Dec 16
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
Still don't see what you're looking for?
See all properties in Upper Matecumbe Key.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

See all hotels in Upper Matecumbe Key
Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Photo by Cameron Abbott
Open Photo by Cameron Abbott

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful. "
Callie 4-night trip
Posted 8 days ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Five Star Hotel Information

If you’re searching for the celebrity treatment, the 5 star hotels in Upper Matecumbe Key are your dreams come true. From sprawling resorts to fancy hot spots, theseUpper Matecumbe Key 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.

Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Upper Matecumbe Key, Islamorada, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Upper Matecumbe Key five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.

Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Upper Matecumbe Key 5 star hotels.

Explore a world of travel with Expedia