
Lower Florida Keys Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Lower Florida Keys
Price found within the past 48 hours. Click for updated prices.

Eden House
Key West Historic District
Price was CA $1,060, price is now CA $845 per person
CA $845
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,001 reviews)
Our stay at Eden House was very enjoyable. The hotel was accessible to Duval Street, Mallory Square, and the harbor area. Very easy walks to everything we wanted to do. The hotel is located in a quiet neighborhood and was a welcome respite after a day of exploring. We recommend this property whole-heartedly and will stay here again when we return. We have visited KW every year since we retired to the Tampa area in 2022.
Reviewed on Jun 21, 2026

The Perry Hotel & Marina Key West
Price was CA $1,509, price is now CA $1,108 per person
CA $1,108
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
Nice hotel. 5 days/4 nights stay. Free parking, but no free breakfast The room came with a fridge and a coffee maker, no microwave. 2 Restaurants in the property, but food is very expensive. Staff at check in don’t even smile at you, when they do it feels forced. Concierges were very nice. The shuttle to Key West is a great feature. One of the two pools was closed. The one pool was packed full every day. Room was great. Tile on the floors, hubby found bed uncomfortable. Our room had one King bed and a coffee table. It felt unfinished. It needs a small sofa or something, so you don’t have to use the bed to sit to eat or work on your laptop. Every room has a very spacious balcony. The gym is very well equipped.
Reviewed on Jun 22, 2026

The Marker Key West Harbor Resort
Key West Historic District
Price was CA $1,319, price is now CA $1,046 per person
CA $1,046
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (1,012 reviews)
Great location. Room overlooking the harbor was great, as spent mornings and evenings on balcony watching all the activities.
Reviewed on Jun 22, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $1,327, price is now CA $1,059 per person
CA $1,059
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (3,399 reviews)
The room and staff were excellent. I guess the bad part of coming this time of the year is the beaches were covered in seaweed that smelled terrible! I mean you could smell it at the pool nearly a block away. The only other thing that needs improvement is the drinks at the bar, I tried various rum runners and daiquiris, all tasted rather bland lacking flavor and alcohol. At $15+ each I expected better.
Reviewed on Jun 22, 2026

The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,288, price is now CA $1,826 per person
CA $1,826
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (1,022 reviews)
The friendliest staff of any hotel I ever stayed.
Reviewed on Jun 21, 2026
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View all trips3 Night Pet-friendly holidays in Lower Florida Keys
Price found within the past 48 hours. Click for updated prices.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $1,384, price is now CA $1,192 per person
CA $1,192
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,399 reviews)
The room and staff were excellent. I guess the bad part of coming this time of the year is the beaches were covered in seaweed that smelled terrible! I mean you could smell it at the pool nearly a block away. The only other thing that needs improvement is the drinks at the bar, I tried various rum runners and daiquiris, all tasted rather bland lacking flavor and alcohol. At $15+ each I expected better.
Reviewed on Jun 22, 2026

The Perry Hotel & Marina Key West
Price was CA $1,953, price is now CA $1,591 per person
CA $1,591
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
Nice hotel. 5 days/4 nights stay. Free parking, but no free breakfast The room came with a fridge and a coffee maker, no microwave. 2 Restaurants in the property, but food is very expensive. Staff at check in don’t even smile at you, when they do it feels forced. Concierges were very nice. The shuttle to Key West is a great feature. One of the two pools was closed. The one pool was packed full every day. Room was great. Tile on the floors, hubby found bed uncomfortable. Our room had one King bed and a coffee table. It felt unfinished. It needs a small sofa or something, so you don’t have to use the bed to sit to eat or work on your laptop. Every room has a very spacious balcony. The gym is very well equipped.
Reviewed on Jun 22, 2026

Pier House Resort & Spa
Key West Historic District
Price was CA $2,072, price is now CA $1,751 per person
CA $1,751
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,180 reviews)
Awesome place to stay. Fun amenities, great staff. Cold AC. Convenient. Excellent!
Reviewed on Jun 18, 2026
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View all trips4 Night Pet-friendly holidays in Lower Florida Keys
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
Price was CA $1,475, price is now CA $1,207 per person
CA $1,207
per person
Aug 26 - Aug 30
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,139 reviews)
I love the property but hated the lizards that roamed the area
Reviewed on Jun 21, 2026

The Key West Hotel
Key West Historic District
Price was CA $2,918, price is now CA $2,255 per person
CA $2,255
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.
Reviewed on Jun 7, 2026

Pier House Resort & Spa
Key West Historic District
Price was CA $2,128, price is now CA $1,750 per person
CA $1,750
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,180 reviews)
Awesome place to stay. Fun amenities, great staff. Cold AC. Convenient. Excellent!
Reviewed on Jun 18, 2026
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View all tripsPet-friendly Hotels in Lower Florida Keys

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! (2,430 reviews)
"The food was amazing! There was a language barrier for the maid staff, but most were very nice. The last three days the place was overrun by little league baseball players and their families. The lobby was packed with screaming, horseplay all hours and both pools were overcrowded with kids as well. ..."
Reviewed on Jun 22, 2026

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,044 reviews)
"I’m extremely disappointed with my stay this weekend. The room was not clean and the condition of the bedding was unacceptable. The sheets and covers were visibly dirty, which made me question whether the room had been properly cleaned before we arrived. On top of the cleanliness issues, the way ..."
Reviewed on Jun 21, 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! (1,816 reviews)
"The pool and all the garden extras were amazing! The food was delicious at the restaurant too. And having the shuttle to downtown was a plus to dealing with parking."
Reviewed on Jun 21, 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

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $62
per adult
94% of travellers recommend

Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $36
per child
88% of travellers recommend

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
CA $76
per adult
86% of travellers recommend
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