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 $17,336
per person
Oct 7 - Oct 14
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) 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 $3,130
per person
Nov 12 - Nov 17
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
I cannot say enough great things about this last experience. The staff were all so caring and incredible, and sooo attentive to all questions and help needed.
Reviewed on Aug 23, 2026
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See all available trips from Columbus to Windley Key
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 $17,336
per person
Oct 7 - Oct 14
found 20 hours ago
Roundtrip flight included
Montreal (YMQ) 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 $3,130
per person
Nov 12 - Nov 17
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
I cannot say enough great things about this last experience. The staff were all so caring and incredible, and sooo attentive to all questions and help needed.
Reviewed on Aug 23, 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 $10,385
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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 $2,224
per person
Nov 13 - Nov 16
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
I cannot say enough great things about this last experience. The staff were all so caring and incredible, and sooo attentive to all questions and help needed.
Reviewed on Aug 23, 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 $12,488
per person
Nov 18 - Nov 22
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
Viscay Hotel
South Beach
CA $1,795
per person
Nov 1 - Nov 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand
Reviewed on Jul 16, 2026
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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! (255 reviews)
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Reviewed on Aug 23, 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! (1,015 reviews)
"Was Great! Everyone was super nice and helpful!"
Reviewed on Aug 23, 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. ...
8.6/10 Excellent! (1,008 reviews)
"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall ..."
Reviewed on Aug 21, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
