Key West Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Key West
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 CA $2,039, price is now CA $1,530 per person
CA $1,530
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.4/10 Very Good! (621 reviews)
Property was nice with great beach location and close to downtown Key West. BUT they screw you with hidden charges. They 67+ per day resort fee was at least disclosed. But we had 2 100 per day (before tax) “beach” charges that were not disclosed and nobody ever mentioned to us. That is ridiculous highway robbery on top of the very pricey room charges so we won’t be going back there!
Reviewed on Apr 27, 2026
DoubleTree Resort by Hilton Grand Key - Key West
Price was CA $2,251, price is now CA $1,774 per person
CA $1,774
per person
Jun 15 - Jun 22
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.2/10 Very Good! (1,008 reviews)
The hotel was clean and offered shuttle service to town making it easy to get around.
Reviewed on Apr 27, 2026
The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,867, price is now CA $2,261 per person
CA $2,261
per person
Jul 18 - Jul 25
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.6/10 Excellent! (1,006 reviews)
Friendly staff, room cleaning could have been better. Last two days of our stay there was no room cleaning performed.
Did not know about the parking fees at the resort until we arrived.
I may have overlooked that while reviewing the property while booking.
Reviewed on Apr 25, 2026
The Gardens Hotel
Old Town Key West
Price was CA $1,958, price is now CA $1,720 per person
CA $1,720
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
This was one of the nicest places we have ever stayed. It felt like a tropical oasis but was only a block over from Duval. Wine tasting room was great and the hotel cat, Lucy, was the sweetest! Breakfast each morning was amazing! We would definitely stay here again when we come back to visit!
Reviewed on Apr 26, 2026
3 Night Pet-friendly holidays in Key West
Price found within the past 48 hours. Click for updated prices.
The Gardens Hotel
Old Town Key West
Price was CA $2,290, price is now CA $1,746 per person
CA $1,746
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
This was one of the nicest places we have ever stayed. It felt like a tropical oasis but was only a block over from Duval. Wine tasting room was great and the hotel cat, Lucy, was the sweetest! Breakfast each morning was amazing! We would definitely stay here again when we come back to visit!
Reviewed on Apr 26, 2026
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $1,917, price is now CA $1,533 per person
CA $1,533
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.4/10 Very Good! (621 reviews)
Property was nice with great beach location and close to downtown Key West. BUT they screw you with hidden charges. They 67+ per day resort fee was at least disclosed. But we had 2 100 per day (before tax) “beach” charges that were not disclosed and nobody ever mentioned to us. That is ridiculous highway robbery on top of the very pricey room charges so we won’t be going back there!
Reviewed on Apr 27, 2026
4 Night Pet-friendly holidays in Key West
Price found within the past 48 hours. Click for updated prices.
DoubleTree Resort by Hilton Grand Key - Key West
Price was CA $1,318, price is now CA $1,061 per person
CA $1,061
per person
Jun 19 - Jun 23
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.2/10 Very Good! (1,008 reviews)
The hotel was clean and offered shuttle service to town making it easy to get around.
Reviewed on Apr 27, 2026
The Perry Hotel & Marina Key West
Price was CA $2,898, price is now CA $2,498 per person
CA $2,498
per person
Jun 4 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
9.4/10 Exceptional! (1,256 reviews)
Excellent location, shuttle is free😍
Reviewed on Apr 26, 2026
The Key West Hotel
Key West Historic District
Price was CA $4,328, price is now CA $3,732 per person
CA $3,732
per person
Jun 4 - Jun 8
found 23 hours ago
Roundtrip flight included
Winnipeg (YWG) to Key West (EYW)
9.2/10 Wonderful! (548 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.
Reviewed on Apr 21, 2026
Pet-friendly Hotels in Key West
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,150 reviews)
We like the pools and the bars there were on location, appreciated having the DJ and live music.
Reviewed on Apr 28, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,810 reviews)
Most of the staff were friendly and helpful. Facilities very clean. Great shuttle to town and airport!
Reviewed on Apr 28, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
8.4/10 Very Good! (634 reviews)
My Mother’s Family lived here during WWll so its was a bucket list hotel for me. Its Worth Staying Here…. been going for a few years now and its very awesome especially with multiple weddings going on, you can swim in ocean, and drive your golf cart to shop and. dine on Duval etc, how can you go ...
Reviewed on Apr 28, 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.
