Florida Keys Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Price was CA $1,971, price is now CA $1,516 per person
CA $1,516
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.8/10 Excellent! (1,275 reviews)
Beautiful resort, only was there for one night, will be back for a longer stay.
Reviewed on Feb 6, 2026
La Siesta Resort & Villas
Matecumbe
Price was CA $2,982, price is now CA $2,012 per person
CA $2,012
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
excellent location very nice simple breakfast close to liz’s of activities great poool
Reviewed on Feb 2, 2026
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $3,127, price is now CA $2,495 per person
CA $2,495
per person
Apr 10 - Apr 14
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Key West (EYW)
8.4/10 Very Good! (433 reviews)
Lovely, relaxing spot away from the action of downtown, but close enough to everything. Great beach and dining areas.
Reviewed on Feb 7, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Price was CA $3,401, price is now CA $2,787 per person
CA $2,787
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (1,010 reviews)
Staff was amazing!!!
The whole place needed a good cleaning.
I have photos. Believe you me…Paris would NOT stay there.
Reviewed on Jan 19, 2026
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View all trips3 Night Pet-friendly holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $2,228, price is now CA $1,551 per person
CA $1,551
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
excellent location very nice simple breakfast close to liz’s of activities great poool
Reviewed on Feb 2, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Price was CA $2,639, price is now CA $2,208 per person
CA $2,208
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (1,010 reviews)
Staff was amazing!!!
The whole place needed a good cleaning.
I have photos. Believe you me…Paris would NOT stay there.
Reviewed on Jan 19, 2026
The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,167, price is now CA $1,856 per person
CA $1,856
per person
Mar 16 - Mar 19
found 20 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.4/10 Very Good! (1,001 reviews)
Hotel was very nice in all respects, but its location on the beach was the best.
Reviewed on Feb 4, 2026
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View all trips4 Night Pet-friendly holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $1,785, price is now CA $1,235 per person
CA $1,235
per person
Apr 10 - Apr 14
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
excellent location very nice simple breakfast close to liz’s of activities great poool
Reviewed on Feb 2, 2026
The Key West Hotel
Key West Historic District
Price was CA $6,681, price is now CA $4,092 per person
CA $4,092
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on Jan 28, 2026
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View all tripsPet-friendly Hotels in Florida Keys
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
9/10 Wonderful! (1,263 reviews)
This is my second time staying at the Parrot Key. Love the hotel. Beautiful property & rooms, plus the staff is always accommodating & pleasant. The hotels location is also great, just a five to eight minute drive to Duval. I would highly recommend staying there.
Reviewed on Feb 3, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,677 reviews)
Loved the ambience, the pool area, and view of water. Tv did not work at first, but was fixed within 30 minutes. Guest staff was very nice. Size of room and view was lovely, but bathroom door was damaged in corner and keurig/type coffee pot did not work. Thought resort fees were high.
Reviewed on Feb 4, 2026
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...
Reviewed on Feb 3, 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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