Hotels in Upper Matecumbe Key

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Check prices for these dates

Tonight
May 19 - May 20
Tomorrow
May 20 - May 21
This weekend
May 23 - May 25
Next weekend
May 30 - Jun 1

Where to stay in Upper Matecumbe Key?

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

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1079)
$247 nightly
The price is $278
May 28 - May 29
Total includes taxes and fees
Cheeca Lodge & Spa
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.

Great weekend hotel deals in Upper Matecumbe Key, FL

Showing deals for:May 30 - Jun 1

Image gallery for Cheeca Lodge & Spa

Private beach, sun loungers, beach umbrellas, beach towels
VIP Access

Cheeca Lodge & Spa

5.0 star property
Islamorada
9.0/10Wonderful (1,079 reviews)
5% off
Price is $1,466
$651 nightly
$1,466 total
Total includes taxes and fees
Cheeca Lodge & Spa

Top landmarks in Upper Matecumbe Key

Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

Matecumbe is home to Florida Keys Brewing Co., so why not stop by during your stay in Islamorada. Islamorada has other activities you might want to enjoy such as Everglades National Park.

See properties in Florida Keys Brewing Co.
Florida Keys Brewing Co.

Learn more about Upper Matecumbe Key

Upper Matecumbe Key is applauded for its cultural attractions such as History of Diving Museum and MoradaWay Arts & Cultural District.

See all hotels in Upper Matecumbe Key
Islamorada showing a beach bar
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What accommodations do travelers like in Upper Matecumbe Key?
The Caribbean Resort, Pines & Palms Resort and Cheeca Lodge & Spa are all accommodations that are popular with guests.
Can I book a refundable accommodation in Upper Matecumbe Key?
If you need the flexibility to change your travel plans to Upper Matecumbe Key, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the “fully refundable” filter to narrow the results down.
Which Upper Matecumbe Key hotels do our guests like for their great location?
Travelers like these properties for their convenient location: Chesapeake Beach Resort, Islander Resort and Hadley House Islamorada.
Where can I stay in Upper Matecumbe Key if I want a budget-friendly accommodation?
Two inexpensive options worth considering are Chesapeake Beach Resort and La Jolla Resort.
Where can I stay in Upper Matecumbe Key if I want a vacation rental instead of a traditional hotel?
If you’re looking for a good alternative to a hotel, browse our selection of 115 vacation homes. In addition, there are 9 apartments and 13 condos.
Why should I book my Upper Matecumbe Key accommodation with Hotels.com?
There are lots of reasons to book your Upper Matecumbe Key trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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