Lower Florida Keys Pet-friendly Vacations
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Top Pet-friendly vacation packages in Lower Florida Keys
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,525, price is now $871 per person
$871
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
The staff were great. The bungalows are so cute. The only issue I can say we had was the door to our patio didn’t close, so you could have just walked back there.
Reviewed on Oct 8, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,524, price is now $1,674 per person
$1,674
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Staff was friendly and accommodating. The concierge booked trips for us and made some great recommendations for us.
Reviewed on Oct 8, 2025
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,539, price is now $1,031 per person
$1,031
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,005 reviews)
Was lead to believe we would get a resort credit on each room I booked (2), as it was stated on my reservation but found out it’s only for the VIP Gold member of Expedia. Charging for parking on top of the high nightly rates is ridiculous. Mattress are worn where you feel the indents on each side with a raise in the middle, plus the slip off the wooden platform making it difficult to get on. Folio was $73 higher on each room when I checked out so now I have a call in for an explanation
Reviewed on Oct 6, 2025
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,297, price is now $918 per person
$918
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,750 reviews)
One of the most enjoyable stays. Staff extremely knowledgeable and friendly. Received texts regarding activities daily-this was a nice touch! Property well staffed and maintained. Nice beach area which is a plus in Key West.
Reviewed on Oct 8, 2025
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See all available trips from Columbus to Lower Florida Keys
View all trips3 Night Pet-friendly vacations in Lower Florida Keys
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 $1,882, price is now $1,433 per person
$1,433
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (347 reviews)
I coundt be able to enjoy the beach because the weather but looks nice
Reviewed on Oct 8, 2025
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $2,298, price is now $1,521 per person
$1,521
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,005 reviews)
Was lead to believe we would get a resort credit on each room I booked (2), as it was stated on my reservation but found out it’s only for the VIP Gold member of Expedia. Charging for parking on top of the high nightly rates is ridiculous. Mattress are worn where you feel the indents on each side with a raise in the middle, plus the slip off the wooden platform making it difficult to get on. Folio was $73 higher on each room when I checked out so now I have a call in for an explanation
Reviewed on Oct 6, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $2,437, price is now $1,682 per person
$1,682
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
The staff were great. The bungalows are so cute. The only issue I can say we had was the door to our patio didn’t close, so you could have just walked back there.
Reviewed on Oct 8, 2025
Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all trips4 Night Pet-friendly vacations in Lower Florida Keys
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,525, price is now $871 per person
$871
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
The staff were great. The bungalows are so cute. The only issue I can say we had was the door to our patio didn’t close, so you could have just walked back there.
Reviewed on Oct 8, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,213, price is now $1,189 per person
$1,189
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
The property was very green, with large plantings and hedged areas. Our room turned out to be a two bedroom cottage with it's own back porch. Everything was stylish and clean. The property is close to dining and the Hemingway House (across the street). Duval Street is only 1 block away with dining, drinking and shows!
I have stayed here before and will stay again.
Reviewed on Oct 6, 2025
Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,971, price is now $1,128 per person
$1,128
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (484 reviews)
Property has a very cozy feel
Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room.
Reviewed on Aug 24, 2025
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See all available trips from Columbus to Lower Florida Keys
View all tripsTop Pet-friendly Lower Florida Keys Hotels
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Dogs can accompany you (fees apply) at this pet-friendly, oceanfront hotel, where they will enjoy pet-approved amenities, like food and water bowls.
8.6/10 Excellent! (1,770 reviews)
"Property was fun, inviting and a great place to relax after a day in Old Town Key West. Shuttle to Old Town was great, food at Margaritaville was very good, staff very friendly. Jimmy Buffett tunes playing all the time was perfect!"
Reviewed on Oct 8, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this luxury, oceanfront hotel.
8.8/10 Excellent! (1,722 reviews)
"Overall just a good placecto saty whike yiur there"
Reviewed on Oct 3, 2025
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West, FL
Hiking and biking trails are ready for you to explore near this oceanfront resort, where dogs and cats can stay for an additional fee.
7.8/10 Good! (1,006 reviews)
"The property is well maintained and clean. Didn't care for the dining options, seemed a little ackward when ordering. When a red package is purchased I suggest giving the quest the menu at check in, since it's a different menu. Shuttle service was excellent, front desk staff was excellent."
Reviewed on Oct 6, 2025
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.
