Raccoon Key Pet-friendly Vacations

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Flight and Pet-friendly hotel deals in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
CA $1,972
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.

Reviewed on Oct 1, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $2,011
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $2,579
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
Save 100% on your flight
CA $2,570
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Eden House

Eden House

Key West Historic District
CA $2,321
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9/10 Wonderful! (1,002 reviews)
Don't see what you're looking for?
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3 Night Pet-friendly holidays in Raccoon Key

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

Eden House

Key West Historic District
CA $2,109
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,002 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $2,690
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
CA $2,285
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.

Reviewed on Oct 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

4 Night Pet-friendly holidays in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Island City House Hotel

Island City House Hotel

Key West Historic District
CA $1,707
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.6/10 Exceptional! (1,003 reviews)
Absolutely stellar property - gorgeous in all respects. Our rooms, the spacious private porch, the grounds, pool, everything. Beds were comfy, staff was helpful, and we all enjoyed Bert's visits to our porch as well. As a former Key West resident, I loved the Old Town location and atmosphere of the Island City House Hotel. The staff were also friendly and helpful. We have every intention of staying here again in the future!

Reviewed on Sep 30, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
CA $2,108
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $2,579
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

Pet-friendly Hotels in Raccoon Key

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay

Key West FL
  • 11 min drive from Duval Street
Stay at this vacation home in Key West. Enjoy private pools, a fitness center, and laundry facilities. Popular attractions Duval Street and Smathers Beach are ...
Suncoast House at Lunara Bay
The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay

Key West FL
  • 11 min drive from Duval Street
Stay at this vacation home in Key West. Enjoy private pools, a fitness center, and a garden. Popular attractions Duval Street and Smathers Beach are located ...
10/10 Exceptional! (28 reviews)
"Great place clean and comfortable."

Reviewed on Sep 20, 2026

The Seagate Estate at Lunara Bay
The Starboard House at Solaire Lunara Bay

The Starboard House at Solaire Lunara Bay

Key West FL
  • 10 min drive from Duval Street
Stay at this vacation home in Key West. Enjoy private pools, a fitness center, and laundry facilities. Popular attractions Duval Street and Smathers Beach are ...
The Starboard House at Solaire Lunara Bay
See all 3,093 properties in Raccoon Key
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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $82
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Raccoon Key

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.