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

Upper Matecumbe Key condominium resorts to rent from $139

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 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, (1,799 reviews)
"Great location"
United States
Dianne
$195 nightly
The price is $219
Oct 20 - Oct 21
Total with taxes and fees
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

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
$280 nightly
The price is $315
Nov 15 - Nov 16
Total with taxes and fees
Islander Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

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
$123 nightly
The price is $139
Oct 21 - Oct 22
Total with taxes and fees
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, (1,326 reviews)
"Pool side bar On the ocean Very clean and friendly"
United States
Ronald
$222 nightly
The price is $250
Nov 17 - Nov 18
Total with taxes and fees
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

5. 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
$244 nightly
The price is $274
Oct 20 - Oct 21
Total with taxes and fees
Cheeca Lodge & Spa
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

6. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice hotel."
United States
Brett
$168 nightly
The price is $189
Oct 22 - Oct 23
Total with taxes and fees
La Jolla 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, (1,004 reviews)
"Great place"
United States
weder
$188 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Hadley Resort and Marina
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

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
$231 nightly
The price is $260
Nov 18 - Nov 19
Total with taxes and fees
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
$534 nightly
The price is $600
Oct 21 - Oct 22
Total with taxes and fees
The Islands of Islamorada
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

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
$248 nightly
The price is $279
Oct 20 - Oct 21
Total with taxes and fees
Pines & Palms Resort
A beachside lounge area with sun loungers, a thatched structure, and a view of the 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
$203 nightly
The price is $228
Oct 22 - Oct 23
Total with taxes and fees
Sands of Islamorada
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

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
$298 nightly
The price is $336
Oct 27 - Oct 28
Total with taxes and fees
Bayside Villas by Islander Resort
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
$3,426 nightly
The price is $3,801
Oct 26 - Oct 27
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Marina

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
$2,284 nightly
The price is $2,534
Oct 26 - Oct 27
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite
Marina

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
$1,142 nightly
The price is $1,267
Oct 26 - Oct 27
Total with taxes and fees
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
$1,860 nightly
The price is $2,064
Oct 26 - Oct 27
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,849 nightly
The price is $2,051
Oct 26 - Oct 27
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
$1,713 nightly
The price is $1,901
Oct 26 - Oct 27
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior

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
$184 nightly
The price is $207
Oct 26 - Oct 27
Total with taxes and fees
Casa Morada
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
$2,282 nightly
The price is $2,532
Oct 26 - Oct 27
Total with taxes and fees
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"clean room and very unique location. The breakfast was just ok and overpriced"
Anna 1-night trip
Posted 4 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
7,153
Accommodation
0 Condo Resorts
Lowest Price
$139
Highest Price
$3,801

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