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 $232

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7
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
9.2 out of 10, Wonderful, (1,802 reviews)
"Great place"
United States
Phelicia
The price is CA $196
CA $301 total
includes taxes & fees
Oct 18 - Oct 19
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, (1,139 reviews)
"Amazing place would definitely recommend"
United States
Steven
The price is CA $331
CA $477 total
includes taxes & fees
Oct 20 - Oct 21
Islander Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Nice hotel."
United States
Brett
The price is CA $180
CA $242 total
includes taxes & fees
Oct 15 - Oct 16
La Jolla Resort
A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

4. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (767 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $140
CA $232 total
includes taxes & fees
Oct 26 - Oct 27
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.

5. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,321 reviews)
"Super clean resort."
United States
Danielle
The price is CA $203
CA $333 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay 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, (1,477 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
The price is CA $239
CA $373 total
includes taxes & fees
Oct 19 - Oct 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, (1,000 reviews)
"Great place"
United States
weder
The price is CA $204
CA $276 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 $240
CA $374 total
includes taxes & fees
Nov 8 - Nov 9
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)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
The price is CA $294
CA $410 total
includes taxes & fees
Oct 15 - Oct 16
Pines & Palms Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

10. 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 $678
CA $856 total
includes taxes & fees
Oct 18 - Oct 19
The Islands of Islamorada
An outdoor dining area with wooden furniture, tables, and chairs, overlooking a beach and ocean.

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 CA $370
CA $520 total
includes taxes & fees
Nov 1 - Nov 2
Bayside Villas by Islander Resort
A wooden deck with a view of the beach and ocean.

12. 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 $269
CA $322 total
includes taxes & fees
Oct 20 - Oct 21
Sands of Islamorada
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 $4,277
CA $5,393 total
includes taxes & fees
Oct 19 - Oct 20
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 $2,851
CA $3,606 total
includes taxes & fees
Oct 19 - Oct 20
Charming Suite @Islamorada With Pool Access - Twilight 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 CA $2,321
CA $2,936 total
includes taxes & fees
Oct 19 - Oct 20
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.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,308
CA $2,919 total
includes taxes & fees
Oct 19 - Oct 20
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.

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 CA $2,139
CA $2,697 total
includes taxes & fees
Oct 20 - Oct 21
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is CA $1,426
CA $1,804 total
includes taxes & fees
Oct 19 - Oct 20
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo 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, (463 reviews)
"Very helpful staff and great location"
United States
David
The price is CA $228
CA $273 total
includes taxes & fees
Oct 28 - Oct 29
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 $2,849
CA $3,602 total
includes taxes & fees
Oct 19 - Oct 20
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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

8/10 Good
"The hotel’s location is fantastic, right on the Gulf side with its own private beach, lounge chairs, and even a small pier. The sunsets were absolutely stunning, and waking up by the water was a real treat. Just a heads up: we booked the economy double room and it was really small; barely enough space for two people and luggage. Still, the outdoor areas more than made up for it."
Betul 1-night trip
Posted 13 hours ago
The Pelican Key Largo Cottages

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cottages information

Number of reviews
5,644
Accommodation
26 Cottages
Lowest Price
CA $232
Highest Price
CA $5,393

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