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

Search Upper Matecumbe Key Cottage Rentals from CA $220

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,799 reviews)
"Great location"
United States
Dianne
The price is CA $196
CA $300 total
includes taxes & fees
Nov 5 - Nov 6
Chesapeake Beach 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.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,146 reviews)
"Great resort for families with children"
United States
Bryan
The price is CA $276
CA $414 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
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, (771 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $130
CA $220 total
includes taxes & fees
Nov 2 - Nov 3
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, (1,327 reviews)
"Pool side bar On the ocean Very clean and friendly"
United States
Ronald
The price is CA $223
CA $355 total
includes taxes & fees
Nov 17 - Nov 18
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, (1,002 reviews)
"Nice hotel."
United States
Brett
The price is CA $202
CA $267 total
includes taxes & fees
Oct 22 - Oct 23
La Jolla Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

6. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,486 reviews)
"Loved the property, staff and rooms"
United States
James
The price is CA $267
CA $404 total
includes taxes & fees
Nov 19 - Nov 20
Cheeca Lodge & Spa
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, (1,004 reviews)
"Great place"
United States
weder
The price is CA $202
CA $274 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $207
CA $336 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

9. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (81 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is CA $686
CA $864 total
includes taxes & fees
Oct 27 - Oct 28
The Islands of Islamorada
A beachside resort with a pool area, lounge chairs, and palm trees.

10. 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 CA $253
CA $363 total
includes taxes & fees
Oct 20 - Oct 21
Pines & Palms Resort
A wooden deck with a view of the beach and ocean.

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 CA $270
CA $323 total
includes taxes & fees
Oct 22 - Oct 23
Sands of Islamorada
An outdoor dining area with wooden furniture, tables, and chairs, overlooking a beach and ocean.

12. 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 CA $304
CA $445 total
includes taxes & fees
Oct 27 - Oct 28
Bayside Villas by Islander Resort
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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 CA $4,242
CA $5,350 total
includes taxes & fees
Oct 25 - Oct 26
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is CA $2,828
CA $3,576 total
includes taxes & fees
Oct 25 - Oct 26
Charming Suite @Islamorada With Pool Access - Twilight Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is CA $1,414
CA $1,789 total
includes taxes & fees
Oct 25 - Oct 26
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.

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is CA $2,302
CA $2,912 total
includes taxes & fees
Oct 25 - Oct 26
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,289
CA $2,895 total
includes taxes & fees
Oct 25 - Oct 26
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is CA $2,121
CA $2,683 total
includes taxes & fees
Oct 25 - Oct 26
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon 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
9.4 out of 10, Exceptional, (464 reviews)
"Very helpful staff and great location"
United States
David
The price is CA $221
CA $265 total
includes taxes & fees
Oct 26 - Oct 27
Casa Morada
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is CA $2,825
CA $3,573 total
includes taxes & fees
Oct 25 - Oct 26
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

La Jolla Resort

La Jolla Resort

8/10 Good
"Just stopped in for a riding break from Ormond Beach to Key West, had a great time and place was conveniently located; we will use this resort again"
Donald 1-night trip
Posted 2 hours ago
La Jolla Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cottages information

Number of reviews
5,828
Accommodation
26 Cottages
Lowest Price
CA $220
Highest Price
CA $5,350

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