Windley Key Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Windley Key
Price found within the past 48 hours. Click for updated prices.
Fontainebleau Miami Beach
Mid Beach
Price was CA $3,021, price is now CA $1,658 per person
CA $1,658
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (8,206 reviews)
This is the only place you need to go to. We don’t even need to leave the resort. They have Everything. Their Italian restaurant is amazing.
Reviewed on May 23, 2026
The Crosby Miami World Center
Downtown Miami
Price was CA $3,355, price is now CA $1,858 per person
CA $1,858
per person
Jun 25 - Jul 1
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (174 reviews)
Stay was great but NO ONSITE PARKING!
Reviewed on May 24, 2026
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View all trips5* Pet-friendly holidays in Windley Key
Price found within the past 48 hours. Click for updated prices.
Andaz Miami Beach Resort & Spa
Mid Beach
Price was CA $2,575, price is now CA $1,546 per person
CA $1,546
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9/10 Wonderful! (284 reviews)
Really lovely upgrade from the Confidant hotel to the Andaz. Staff was extremely friendly and helpful in every way. Room was clean and spacious and loved the beach and pool service as well. Take a yoga or pilates class on the roof if you can - the view is amazing!
Reviewed on May 15, 2026
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View all trips3 Night Pet-friendly holidays in Windley Key
Price found within the past 48 hours. Click for updated prices.
1 Hotel South Beach
South Beach
Price was CA $3,983, price is now CA $2,508 per person
CA $2,508
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,511 reviews)
Great sized room ocean view was nice place was spotless can’t recommend enough
Reviewed on May 23, 2026
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View all trips4 Night Pet-friendly holidays in Windley Key
Price found within the past 48 hours. Click for updated prices.
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View all tripsPet-friendly Hotels in Windley Key
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (198 reviews)
"My only suggestion is to clean the garbage littered in the beach-lounging area. There’s also litter in the ocean (under Little Limon deck) that we picked up and a strong smell of sewage that hits the nostrils as soon as we exit our room or walk towards the Tiki bar. The ice cream place also needs ..."
Reviewed on May 16, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,003 reviews)
"Beautiful beach area was really nice As well as and staff and breakfast"
Reviewed on May 23, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
"Excellent"
Reviewed on May 10, 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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