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

Search Cottages in Upper Matecumbe Key

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,805 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is HK$1,185
HK$1,774 total
includes taxes & fees
3 Nov - 4 Nov
Chesapeake Beach Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,497 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is HK$1,422
HK$2,174 total
includes taxes & fees
29 Nov - 30 Nov
Cheeca Lodge & Spa
A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

3. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is HK$542
HK$1,017 total
includes taxes & fees
3 Nov - 4 Nov
Breezy Palms Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is HK$1,319
HK$2,057 total
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

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 HK$983
HK$1,327 total
includes taxes & fees
4 Nov - 5 Nov
La Jolla Resort
A patio with a wooden table and chairs, a sofa, and a striped ottoman. There are palm trees and a view of the beach.

6. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,160 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 HK$1,820
HK$2,621 total
includes taxes & fees
3 Nov - 4 Nov
Islander Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

7. 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 HK$1,123
HK$1,519 total
includes taxes & fees
15 Nov - 16 Nov
Hadley Resort and Marina
A resort with a pool surrounded by palm trees and a view of the ocean.

8. 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 HK$1,213
HK$1,938 total
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas
A beachside resort with a pool area, lounge chairs, and palm trees.

9. 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 HK$1,500
HK$2,120 total
includes taxes & fees
4 Nov - 5 Nov
Pines & Palms Resort
A wooden deck with a view of the beach and ocean.

10. 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 HK$1,506
HK$1,800 total
includes taxes & fees
16 Nov - 17 Nov
Sands of Islamorada
A covered outdoor area with a lounge chair and ottoman, surrounded by tropical plants and palm trees, leading to a pool area.

11. 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 HK$1,883
HK$2,692 total
includes taxes & fees
3 Nov - 4 Nov
Bayside Villas by Islander Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

12. 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 HK$5,366
HK$6,610 total
includes taxes & fees
30 Nov - 1 Dec
The Islands of Islamorada
A pool with a view of a bridge and umbrellas in the background.

13. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is HK$23,534
HK$27,300 total
includes taxes & fees
9 Nov - 10 Nov
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
A pool with a view of a bridge and umbrellas in the background.

14. Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is HK$7,845
HK$9,500 total
includes taxes & fees
8 Nov - 9 Nov
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
A covered outdoor area with a white railing, a table with a straw hat, and a bench.

15. Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is HK$12,771
HK$15,458 total
includes taxes & fees
8 Nov - 9 Nov
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
A pool with a view of a bridge and umbrellas in the background.

16. Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is HK$15,690
HK$18,992 total
includes taxes & fees
8 Nov - 9 Nov
Charming Suite @Islamorada With Pool Access - Twilight Suite
A pool with a view of a bridge and umbrellas in the background.

17. Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is HK$11,767
HK$14,242 total
includes taxes & fees
8 Nov - 9 Nov
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
A pool with a view of a bridge and umbrellas in the background.

18. Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is HK$12,701
HK$15,371 total
includes taxes & fees
8 Nov - 9 Nov
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
A view from a window overlooking a beach with palm trees and a wooden pier.

19. 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 HK$1,440
HK$1,709 total
includes taxes & fees
4 Nov - 5 Nov
Casa Morada
A pool with a view of a bridge and umbrellas in the background.

20. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is HK$15,674
HK$18,512 total
includes taxes & fees
3 Dec - 4 Dec
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
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.
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Excellent stay would definitely stay again"
Lisa D 1-night trip
Posted 10 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cottages information

Number of reviews
5,082
Accommodation
27 Cottages
Lowest Price
HK$1,017
Highest Price
HK$27,300

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