A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Find Cheap Hotels in Upper Matecumbe Key, FL

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Our top choices for Upper Matecumbe Key cheap hotels

1. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is £617
includes taxes & fees
30 Nov - 1 Dec
The Islands of Islamorada

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,810 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is £161
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,161 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is £220
includes taxes & fees
15 Nov - 16 Nov
Islander Resort

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,503 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is £207
includes taxes & fees
29 Nov - 30 Nov
Cheeca Lodge & Spa

5. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is £132
includes taxes & fees
8 Nov - 9 Nov
La Jolla Resort

6. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (466 reviews)
"Very helpful staff and great location"
United States
David
The price is £162
includes taxes & fees
17 Nov - 18 Nov
Casa Morada

7. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is £202
includes taxes & fees
15 Nov - 16 Nov
Pines & Palms Resort

8. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (778 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is £97
includes taxes & fees
10 Nov - 11 Nov
Breezy Palms Resort

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is £239
includes taxes & fees
11 Nov - 12 Nov
Bayside Villas by Islander Resort

10. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,325 reviews)
"Great location as well."
United States
Amir
The price is £186
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort

11. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
United States
Nicolas
The price is £171
includes taxes & fees
16 Nov - 17 Nov
Sands of Islamorada

12. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is £184
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas

13. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is £144
includes taxes & fees
17 Nov - 18 Nov
Hadley Resort and Marina
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 out more about Upper Matecumbe Key

How to get cheap hotels in Upper Matecumbe Key?

 

✅ The length of stay in Upper Matecumbe Key often varies depending on the nature of the trip, but many travellers opt to stay for several days or up to a week to take in Upper Matecumbe Key's notable landmarks and points of interest.

✅  If you're looking for cheap hotels in Upper Matecumbe Key in 2026, book your hotel well in advance. Reserving your stay at least a few weeks or months ahead of time can help you take advantage of amazing rates on cheap hotels in Upper Matecumbe Key, and if your plans change you can find many options of hotels with free cancelation.

✅  To find affordable hotels in Upper Matecumbe Key on Expedia, start by entering your travel dates and the number of individuals in your group. Once you've provided this information, you can refine your search results by filtering for budget hotels in Upper Matecumbe Key.

✅  Use the filtering tools offered by Expedia to refine your search results by location, price limits, amenities such as breakfast included, and other factors that matter to you. This will help you quickly locate the ideal budget-friendly hotel that fits your specific requirements.

✅  If you're looking to save money on a cheap hotel in Upper Matecumbe Key, the ideal time to go is usually during the off-season in Upper Matecumbe Key. On Expedia, you can find hotels from £97*.

✅  Upper Matecumbe Key offers numerous budget-friendly attractions and activities for travellers, such as art and exhibits at free museums and galleries or exploring Upper Matecumbe Key on foot.

✅  One of the best ways to find cheap hotels in Upper Matecumbe Key is to search Expedia for properties that provide family-friendly accommodations and features such as activities and complimentary meals, and then sort these by price.

*Prices and availability are subject to change. Additional terms may apply.

Top Upper Matecumbe Key Hotel Reviews

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