Find beach hotels in Upper Matecumbe Key, FL from CA $93

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Top Upper Matecumbe Key Beach Hotel

Our top choices for Upper Matecumbe Key beach hotels

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1004)
"I love staying here! Old Florida charm and convenient to great restaurants!"
The price is CA $106
CA $158 total
includes taxes & fees
Sep 11 - Sep 12
La Jolla Resort

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1515)
"Great place"
The price is CA $168
CA $267 total
includes taxes & fees
Sep 3 - Sep 4
Chesapeake Beach Resort

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (1001)
"Clean, nice beach and pool area we had a great time. Highly recommend it."
The price is CA $157
CA $252 total
includes taxes & fees
Sep 14 - Sep 15
Pines & Palms Resort

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1022)
"Excellent property for a relaxing getaway. "
The price is CA $220
CA $341 total
includes taxes & fees
Sep 8 - Sep 9
Islander Resort

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (524)
"Best kept secret, love staying here,!"
The price is CA $93
CA $175 total
includes taxes & fees
Sep 7 - Sep 8
Breezy Palms Resort

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1251)
"Excellent stay"
The price is CA $231
CA $351 total
includes taxes & fees
Sep 4 - Sep 5
Amara Cay Resort

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1012)
"perfect family hotel with a keys flare."
The price is CA $189
CA $304 total
includes taxes & fees
Sep 30 - Oct 1
La Siesta Resort & Villas

Bayside Villas by Islander Resort

3.5 star property
8.8 out of 10, Excellent, (384)
"Great place to stay"
The price is CA $257
CA $382 total
includes taxes & fees
Sep 24 - Sep 25
Bayside Villas by Islander Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1178)
"amazing stay"
The price is CA $214
CA $334 total
includes taxes & fees
Sep 3 - Sep 4
Cheeca Lodge & Spa

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (387)
"Quiet place which made it a great place to sit and enjoy the view of the water."
The price is CA $221
CA $267 total
includes taxes & fees
Sep 7 - Sep 8
Sands of Islamorada
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.

Beach hotels with pools in Upper Matecumbe Key

Beach hotels with ocean views in Upper Matecumbe Key

4-star beach hotels in Upper Matecumbe Key

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.

Find out more about Upper Matecumbe Key

Find out more about Upper Matecumbe Key

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