Florida Keys Pet-friendly Vacations
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Top Pet-friendly vacation packages in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Islander Resort
Matecumbe
Price was $990, price is now $856 per person
$856
per person
Dec 11 - Dec 13
found 6 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
9.4/10 Exceptional! (1,147 reviews)
Sunrise was beautiful. Loved the private seating out back.
Arrived at night and it is not well signed or lit. Bathroom layout with the sink in the bedroom was odd and there was no vanity space to set anything. Menu at the resteraunt was limited. Not all items were available. The value for the money was fair at best. They have a resort fee for limited features
Reviewed on Nov 10, 2026
The Gardens Hotel
Old Town Key West
Price was $1,472, price is now $1,190 per person
$1,190
per person
Jan 11 - Jan 13
found 11 hours ago
Roundtrip flight included
Charleston (CHS) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West
Reviewed on Nov 8, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Price was $1,591, price is now $1,438 per person
$1,438
per person
Dec 11 - Dec 16
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,190 reviews)
The hotel is lovely and the service was excellent. Some construction going on while we were there directly outside of our room.
Reviewed on Nov 10, 2026
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View all trips3 Night Pet-friendly vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Price was $780, price is now $547 per person
$547
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,190 reviews)
The hotel is lovely and the service was excellent. Some construction going on while we were there directly outside of our room.
Reviewed on Nov 10, 2026
Islander Resort
Matecumbe
Price was $697, price is now $514 per person
$514
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.4/10 Exceptional! (1,147 reviews)
Sunrise was beautiful. Loved the private seating out back.
Arrived at night and it is not well signed or lit. Bathroom layout with the sink in the bedroom was odd and there was no vanity space to set anything. Menu at the resteraunt was limited. Not all items were available. The value for the money was fair at best. They have a resort fee for limited features
Reviewed on Nov 10, 2026
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See all available trips from Columbus to Florida Keys
View all trips4 Night Pet-friendly vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
The Key West Hotel
Key West Historic District
Price was $2,728, price is now $1,904 per person
$1,904
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Key West (EYW)
9.2/10 Wonderful! (564 reviews)
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!
Reviewed on Oct 29, 2026
The Gardens Hotel
Old Town Key West
Price was $3,034, price is now $2,369 per person
$2,369
per person
Jan 11 - Jan 15
found 1 hour ago
Roundtrip non-stop flight included
Green Bay (GRB) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West
Reviewed on Nov 8, 2026
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View all tripsTop Pet-friendly Florida Keys Hotels
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
With pet-friendly amenities like food and water bowls, this family-friendly, oceanfront hotel welcomes dogs (fees apply). Don't forget to check out nearby Bayview ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Four-legged friends will appreciate the amenities, such as food and water bowls, during their stay (fees apply) at this pet-friendly hotel.
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Dogs and cats are welcome (fees apply) at this pet-friendly, oceanfront resort. If you'd like to stretch your legs, look no further than nearby Bayview ...
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.
Things to do
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
$59
per adult
94% of travellers recommend
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
