Upper Matecumbe Key Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $13,037
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Nobu Hotel Miami Beach
Mid Beach
CA $1,718
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,484 reviews)
My girlfriend and I stay at the Nobu every time we come into Miami. Great spot for a weekend stay!
Reviewed on Aug 29, 2026
Southernmost House - Adult Exclusive
Old Town Key West
CA $3,456
per person
Oct 20 - Oct 25
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Super nice and clean, staff was wonderful w knowledge of the history of the mansion
Reviewed on Aug 24, 2026
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View all trips5* Pet-friendly holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Miami Beach
Mid Beach
CA $1,718
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,484 reviews)
My girlfriend and I stay at the Nobu every time we come into Miami. Great spot for a weekend stay!
Reviewed on Aug 29, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $13,037
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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See all available trips from Columbus to Upper Matecumbe Key
View all trips3 Night Pet-friendly holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips4 Night Pet-friendly holidays in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
The Local House
South Beach
CA $1,131
per person
Nov 10 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Great location on Ocean Drive, few mins walk to the main restaurants/bars. Rooftop pool was lovely after a day at the beach. Great to have sunbeds/towels provided for the beach which is a 5 minute walk across the road.
Room was really nice with coffee machine and great view from the balcony.
Check in was easy, 100$ security deposit for each night n weed to be paid which I don’t know about. Would 10000% stay again.
Reviewed on Aug 29, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $9,971
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Omni Fort Lauderdale Hotel
East Fort Lauderdale
CA $1,343
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.6/10 Exceptional! (572 reviews)
Omni does it right! Great place to be. All staff are very nice and welcoming. They all seemed to be trained exceptionally well here. The pool area is the highlight. Well done!
Reviewed on Aug 28, 2026
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View all tripsPet-friendly Hotels in Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
- 10 min drive from Bud n' Mary's Dive Center
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
- 5 min walk from Bud n' Mary's Dive Center
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,298 reviews)
"Our stay at Amara Cay Resort was not as expected. The location was nice, and the personnel friendly. However, there were several areas that could use significant improvement, especially considering the price. My biggest concern was the pool area. There was no personnel supervising the pool, and I ..."
Reviewed on Aug 29, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
- 6 min drive from Bud n' Mary's Dive Center
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,108 reviews)
"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"
Reviewed on Aug 28, 2026
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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