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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,586
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
1 Hotel South Beach
South Beach
CA $6,395
per person
Dec 31 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,654 reviews)
I loved this hotel, it was a great location, clean beach, Good beach side cocktails, clean towels.
My only complaint was the restaurants closed at 6:00. The only options to eat after 6:00 in the hotel were apples in the lobby or the mini bar. We arrived late and were hungry, there was nothing to eat at the hotel and the neighborhood restaurants were booked. We ended up buying snacks from a close by CVS.
Reviewed on Oct 13, 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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,586
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
1 Hotel South Beach
South Beach
CA $6,395
per person
Dec 31 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,654 reviews)
I loved this hotel, it was a great location, clean beach, Good beach side cocktails, clean towels.
My only complaint was the restaurants closed at 6:00. The only options to eat after 6:00 in the hotel were apples in the lobby or the mini bar. We arrived late and were hungry, there was nothing to eat at the hotel and the neighborhood restaurants were booked. We ended up buying snacks from a close by CVS.
Reviewed on Oct 13, 2026
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See all available trips from Columbus to Windley Key
View all trips3 Night Pet-friendly holidays in Windley Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,586
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
1 Hotel South Beach
South Beach
CA $5,307
per person
Dec 27 - Dec 30
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,654 reviews)
I loved this hotel, it was a great location, clean beach, Good beach side cocktails, clean towels.
My only complaint was the restaurants closed at 6:00. The only options to eat after 6:00 in the hotel were apples in the lobby or the mini bar. We arrived late and were hungry, there was nothing to eat at the hotel and the neighborhood restaurants were booked. We ended up buying snacks from a close by CVS.
Reviewed on Oct 13, 2026
Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all trips4 Night Pet-friendly holidays in Windley Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $23,537
per person
Dec 29 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Windley Key
View all tripsPet-friendly Hotels in Windley Key
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
- 10 min walk from Theater of the Sea
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! (291 reviews)
"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"
Reviewed on Oct 12, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
- 5 min walk from Theater of the Sea
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! (1,004 reviews)
"It was EXACTLY what I was looking for. Thank you! I wish I had more time to enjoy the super adorable room."
Reviewed on Oct 12, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
- 8 min walk from Theater of the Sea
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. ...
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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