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 $138

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21
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, (1,800 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
$188 nightly
The price is $212
Nov 10 - Nov 11
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, (1,155 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
$303 nightly
The price is $340
Nov 1 - Nov 2
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, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
$123 nightly
The price is $138
Nov 3 - Nov 4
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, (1,324 reviews)
"Great location as well."
United States
Amir
$220 nightly
The price is $248
Nov 15 - Nov 16
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, (1,487 reviews)
"Beautiful resort"
United States
Patricia
$224 nightly
The price is $252
Oct 31 - Nov 1
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, (1,002 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
$208 nightly
The price is $234
Nov 8 - Nov 9
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, (1,000 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
$178 nightly
The price is $200
Oct 31 - Nov 1
Total with taxes and fees
Hadley Resort and Marina
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

8. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
$272 nightly
The price is $306
Nov 19 - Nov 20
Total with taxes and fees
Pines & Palms Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

9. 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
$237 nightly
The price is $266
Nov 15 - Nov 16
Total with taxes and fees
La Siesta Resort & Villas
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

10. 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
$311 nightly
The price is $350
Nov 2 - Nov 3
Total with taxes and fees
Bayside Villas by Islander 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
$204 nightly
The price is $230
Nov 16 - Nov 17
Total with taxes and fees
Sands of Islamorada
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)
"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
$675 nightly
The price is $759
Nov 29 - Nov 30
Total with taxes and fees
The Islands of Islamorada
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
Nov 6 - Nov 7
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
Nov 6 - Nov 7
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
Nov 6 - Nov 7
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
Nov 6 - Nov 7
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
Nov 6 - Nov 7
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
Nov 6 - Nov 7
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
9.2 out of 10, Wonderful, (466 reviews)
"Very helpful staff and great location"
United States
David
$214 nightly
The price is $241
Nov 2 - Nov 3
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
Nov 6 - Nov 7
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

Islander Resort

Islander Resort

10/10 Excellent
"We had a great honeymoon at the islander. The staff was very helpful, Te was great when helping us use the amenities and Chris was the best waiter at Drift!"
Emma 4-night trip
Posted 2 hours ago
Islander Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
6,234
Accommodation
0 Condo Resorts
Lowest Price
$138
Highest Price
$3,801

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