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.
La Siesta Resort & Villas
Matecumbe
Price was $731, price is now $658 per person
$658
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chattanooga (CHA) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
The check in staff was amazing and helpful. There was a lot of included things to do that were really nice and easy to access. There was a strong fish smell, but that was likely because people catch/clean their fish at the dock and there was a bit of sea grass along the shore that likely contributed. We'd stay there again for sure!
Reviewed on Aug 3, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Price was $1,126, price is now $1,015 per person
$1,015
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chattanooga (CHA) to Miami (MIA)
8.6/10 Excellent! (1,156 reviews)
A wonderful family friendly resort! We had a great time and would def come back.
Reviewed on Aug 4, 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.
La Siesta Resort & Villas
Matecumbe
Price was $731, price is now $658 per person
$658
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Chattanooga (CHA) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
The check in staff was amazing and helpful. There was a lot of included things to do that were really nice and easy to access. There was a strong fish smell, but that was likely because people catch/clean their fish at the dock and there was a bit of sea grass along the shore that likely contributed. We'd stay there again for sure!
Reviewed on Aug 3, 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
Save 100% on your flight
Price was $2,024, price is now $1,387 per person
$1,387
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on Jul 27, 2026
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View all tripsTop Pet-friendly Florida Keys Hotels
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
This family-friendly, oceanfront hotel welcomes four-legged friends (fees apply) and offers pet-friendly amenities, like a dog park. While you're here, hike ...
8.6/10 Excellent! (2,602 reviews)
"The back yard/ pool/ and bars areas were AMAZING! The staff were nice and anyways there to help and care for our needs/ wants. I loved the fact the shuttle is so easy to use with the hotel being farther away from old town. The shuttle made it so easy to enjoy our trip without worrying about driving ..."
Reviewed on Aug 6, 2026
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 ...
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 ...
8.6/10 Excellent! (825 reviews)
"Room wouldn’t stay cool, and smelled like musty mildew. Kept getting locked out of room due to software and tech issues, which also caused us not being able to put food and beverage or items on our room number. Pretty beach and fun pool area with live music. Beautiful property."
Reviewed on Aug 6, 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.
Things to do
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$69
per adult
88% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
80% of travellers recommend
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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.
