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 $190

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Recommended hotels in Upper Matecumbe Key

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,813 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
$204 nightly
The price is $229
Nov 19 - Nov 20
Total with taxes and fees
Chesapeake Beach Resort

2. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,339 reviews)
"Great location as well."
United States
Amir
$222 nightly
The price is $250
Nov 15 - Nov 16
Total with taxes and fees
Amara Cay Resort

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,165 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
$267 nightly
The price is $300
Nov 15 - Nov 16
Total with taxes and fees
Islander Resort

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
$169 nightly
The price is $190
Nov 18 - Nov 19
Total with taxes and fees
La Jolla Resort

5. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,516 reviews)
"Clean room, friendly staff and food was good."
United States
Nicholas
$240 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
Cheeca Lodge & Spa

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
$179 nightly
The price is $202
Nov 12 - Nov 13
Total with taxes and fees
Breezy Palms Resort

7. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
$288 nightly
The price is $324
Nov 15 - Nov 16
Total with taxes and fees
Pines & Palms Resort

8. 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
Nov 12 - Nov 13
Total with taxes and fees
Hadley Resort and Marina

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

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
$359 nightly
The price is $404
Nov 18 - Nov 19
Total with taxes and fees
Bayside Villas by Islander Resort

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

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
$779 nightly
The price is $876
Nov 22 - Nov 23
Total with taxes and fees
The Islands of Islamorada

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

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
$3,256 nightly
The price is $3,631
Nov 18 - Nov 19
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
$2,171 nightly
The price is $2,421
Nov 18 - Nov 19
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
$1,086 nightly
The price is $1,211
Nov 18 - Nov 19
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
$1,767 nightly
The price is $1,971
Nov 18 - Nov 19
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,757 nightly
The price is $1,959
Nov 18 - Nov 19
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
$1,628 nightly
The price is $1,816
Nov 18 - Nov 19
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

19. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (467 reviews)
"Very helpful staff and great location"
United States
David
$214 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
Casa Morada

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
$2,169 nightly
The price is $2,419
Nov 18 - Nov 19
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

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Upper Matecumbe Key Condo Resorts information

Number of reviews
4,449
Accommodation
0 Condo Resorts
Lowest Price
$190
Highest Price
$3,631

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