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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 Marathon Florida Keys, Curio by Hilton

CA $914

per person

Sep 2 - Sep 6

found 23 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Miami (MIA)

8.6/10 Excellent! (1,157 reviews)

beautiful and very clean

Reviewed on Jun 18, 2026

La Siesta Resort & Villas

Matecumbe

CA $1,357

per person

Jul 27 - Aug 1

found 18 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.6/10 Excellent! (1,012 reviews)

Service great room great room service good breakfast big room, nice pool, friendly staff great views amazing views I used voice text so I’m sorry this makes no sense. Will be staying again it was my second time here.

Reviewed on Jun 17, 2026

Islander Resort

Matecumbe

CA $1,554

per person

Jul 27 - Aug 1

found 18 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

9.4/10 Exceptional! (1,040 reviews)

Absolutely beautiful property. Feels like you’re in the Caribbean. Nicely decorated rooms. Good location to restaurants.

Reviewed on Jun 18, 2026

The Gardens Hotel

Old Town Key West

CA $1,725

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Great place! The breakfast was excellent, cooked to serve daily! Great options! Annette was the best! The room was very comfortable! The staff was very helpful and kind. We will be back again!

Reviewed on Jun 10, 2026

The Reach Key West, Curio Collection by Hilton

Old Town Key West

CA $2,170

per person

Aug 1 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (1,022 reviews)

Absolutely loved it!!

Reviewed on Jun 19, 2026

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3 Night Pet-friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.

DoubleTree Resort by Hilton Grand Key - Key West

CA $1,074

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.4/10 Very Good! (1,045 reviews)

Would absolutely stay again! Staying in Key West for a fraction of the cost. Daily resort fee included bottled water, famous double tree cookies, shuttles every hour on the hour down to old town, shuttles to airport and Fury Watersports, as well as the use of the changing/shower room upon checkout, should you choose to stay and use the pool. Overall, it was quiet, clean, peaceful, and the pool was amazing. Major bonus points for having a hot tub also. OO, there is also a bar and restaurant on site and a small grocery/coviennent store next to the hotel. 10/10

Reviewed on Jun 19, 2026

The Gardens Hotel

Old Town Key West

CA $1,725

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Great place! The breakfast was excellent, cooked to serve daily! Great options! Annette was the best! The room was very comfortable! The staff was very helpful and kind. We will be back again!

Reviewed on Jun 10, 2026

Hyatt Centric Key West Resort and Spa

Key West Historic District

CA $1,583

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

We had the most amazing experience specially at the bar with Amber was amazing. She knew exactly what my pup wanted shaking but not stir.

Reviewed on Jun 16, 2026

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4 Night Pet-friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

CA $918

per person

Aug 12 - Aug 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

8.6/10 Excellent! (1,157 reviews)

beautiful and very clean

Reviewed on Jun 18, 2026

The Key West Hotel

Key West Historic District

CA $2,045

per person

Aug 24 - Aug 28

found 15 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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

The Gardens Hotel

Old Town Key West

CA $1,816

per person

Aug 24 - Aug 28

found 15 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Great place! The breakfast was excellent, cooked to serve daily! Great options! Annette was the best! The room was very comfortable! The staff was very helpful and kind. We will be back again!

Reviewed on Jun 10, 2026

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Pet-friendly Hotels in Florida Keys

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

30 min drive from Florida Keys Beaches

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! (2,421 reviews)

"Muy limpió y muy buen lugar para ir de vacaciones."

Reviewed on Jun 20, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

29 min drive from Florida Keys Beaches

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! (1,042 reviews)

"Would absolutely stay again! Staying in Key West for a fraction of the cost. Daily resort fee included bottled water, famous double tree cookies, shuttles every hour on the hour down to old town, shuttles to airport and Fury Watersports, as well as the use of the changing/shower room upon checkout, ..."

Reviewed on Jun 19, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

33 min drive from Florida Keys Beaches

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! (1,812 reviews)

"The beach shuttle was great. Due to the location of the hotel and the sargassum, it smelled horrible and you couldn’t use the beach. At the pool, there was a bees nest near the pool so the bees were everywhere. They were told by several people, but never handled during our stay. The bed was also ..."

Reviewed on Jun 19, 2026

See all 8,301 properties in Florida Keys

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.