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Upper Matecumbe Key Hotel Guide - Pet Friendly Hotels in Upper Matecumbe Key, Islamorada

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Our top choices for Upper Matecumbe Key pet-friendly hotels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1609)
"The entire resort was wonderful."
Canada
Mat
The price is €229
includes taxes & fees
25 Jan - 26 Jan 2026
Chesapeake Beach Resort

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (394)
"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
The price is €185
includes taxes & fees
5 Jan - 6 Jan 2026
Sands of Islamorada

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1006)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
The price is €398
includes taxes & fees
14 Jan - 15 Jan 2026
Islander Resort

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1000)
"Good beds, clean room close to Loreleis for sunset dinner. Easy location for Islamorada activities"
United States
Celeste
The price is €159
includes taxes & fees
13 Jan - 14 Jan 2026
Sunset Inn

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1000)
"Patio nice , pool area good , good walk to things to do ,dive museum , brewery, shopping. "
United States
John
The price is €170
includes taxes & fees
11 Jan - 12 Jan 2026
Hadley Resort and Marina

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1271)
"Friendly staff and beautiful property !"
United States
ron
The price is €287
includes taxes & fees
8 Jan - 9 Jan 2026
Amara Cay Resort

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1000)
"Great accommodations, very peaceful setting "
United States
Susan
The price is €261
includes taxes & fees
6 Jan - 7 Jan 2026
La Siesta Resort & Villas

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (404)
"Beautiful stay!!!"
United States
Lakyne
The price is €333
includes taxes & fees
7 Jan - 8 Jan 2026
Bayside Villas by Islander Resort

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (417)
"always a pleasant stay."
United States
robert
The price is €467
includes taxes & fees
6 Jan - 7 Jan 2026
Casa Morada

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is €1,106
includes taxes & fees
7 Jan - 8 Jan 2026
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo 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.

Top Upper Matecumbe Key Hotel Reviews

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