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.
The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was $881, price is now $671 per person
$671
per person
Nov 22 - Nov 24
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (1,009 reviews)
Ty was the best bartender. He makes the best drinks and very friendly to everyone sitting at the bar. Food was good.
Reviewed on Oct 22, 2025
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Save 100% on your flight
Price was $1,472, price is now $975 per person
$975
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,270 reviews)
Beautiful property, rooms were very clean and spacious. Pools were great. Towels could be hard to come by. Everything was great!!
Reviewed on Oct 18, 2025
Islander Resort
Matecumbe
Save 100% on your flight
Price was $1,672, price is now $1,357 per person
$1,357
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Miami (MIA)
9.2/10 Wonderful! (1,014 reviews)
Staff was great at the front desk. Resort was very relaxing.
Reviewed on Oct 22, 2025
The Gardens Hotel
Old Town Key West
Price was $1,705, price is now $1,393 per person
$1,393
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Clean room and beautiful garden. Unfortunately the second morning when we were there, there's a heavy rain, we can't enjoy the garden.
Reviewed on Oct 17, 2025
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was $1,531, price is now $1,254 per person
$1,254
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (396 reviews)
Yes property is in an excellent location and the rooms and common areas were very good.
Reviewed on Oct 22, 2025
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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.
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was $1,279, price is now $1,040 per person
$1,040
per person
Nov 22 - Nov 25
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Key West (EYW)
8.4/10 Very Good! (396 reviews)
Yes property is in an excellent location and the rooms and common areas were very good.
Reviewed on Oct 22, 2025
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Price was $1,479, price is now $1,056 per person
$1,056
per person
Dec 24 - Dec 27
found 10 hours ago
Roundtrip flight included
Trenton (TTN) to Miami (MIA)
8.8/10 Excellent! (1,270 reviews)
Beautiful property, rooms were very clean and spacious. Pools were great. Towels could be hard to come by. Everything was great!!
Reviewed on Oct 18, 2025
The Gardens Hotel
Old Town Key West
Price was $1,705, price is now $1,393 per person
$1,393
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Clean room and beautiful garden. Unfortunately the second morning when we were there, there's a heavy rain, we can't enjoy the garden.
Reviewed on Oct 17, 2025
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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 $3,408, price is now $2,049 per person
$2,049
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9.2/10 Wonderful! (498 reviews)
Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again.
Reviewed on Oct 17, 2025
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Save 100% on your flight
Price was $1,472, price is now $975 per person
$975
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,270 reviews)
Beautiful property, rooms were very clean and spacious. Pools were great. Towels could be hard to come by. Everything was great!!
Reviewed on Oct 18, 2025
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View all tripsTop Pet-friendly Florida Keys Hotels
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this luxury, oceanfront hotel.
8.8/10 Excellent! (1,742 reviews)
The hotel was very clean, nice staff, the room was beautiful and comfortable
Reviewed on Oct 19, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Dogs can accompany you (fees apply) at this pet-friendly, oceanfront hotel, where they will enjoy pet-approved amenities, like food and water bowls.
8.6/10 Excellent! (1,786 reviews)
Awesome! They had great transportation from renting something to drive to a free shuttle bus with complimentary tips, to beautiful rooms, staff was great, bar was wonderful, just all around GREAT place to stay with all u need.
Reviewed on Oct 20, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
This pet-friendly oceanfront resort will accommodate both you and your four-legged companion (additional fees apply for pets). While you're here, enjoy the nearby ...
8.2/10 Very Good! (400 reviews)
This hotel is beautiful. Great view from the room. Staff is amazing
Reviewed on Oct 19, 2025
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.