Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Pet-friendly vacation packages in Florida Keys

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

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$909

per person

Feb 8 - Feb 12

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,320

per person

Feb 8 - Feb 12

found 3 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Private Beach is Amazing !!

Reviewed on Dec 7, 2025

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

$1,465

per person

Feb 8 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Excellent experience. Excellent staff Ultra clean All in all, great location, ambiance and value.

Reviewed on Dec 7, 2025

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,532

per person

Feb 9 - Feb 12

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton

$1,904

per person

Feb 8 - Feb 13

found 1 day ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Miami (MIA)

8.6/10 Excellent! (1,010 reviews)

Staff was amazing and process was fast and painless

Reviewed on Dec 8, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Pet-friendly vacations in Florida Keys

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

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$682

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,389

per person

Feb 10 - Feb 13

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Private Beach is Amazing !!

Reviewed on Dec 7, 2025

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,532

per person

Feb 9 - Feb 12

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Pet-friendly vacations in Florida Keys

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

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Save 100% on your flight

$727

per person

Jan 8 - Jan 12

found 4 hours ago

Roundtrip non-stop flight included

Syracuse (SYR) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Excellent experience. Excellent staff Ultra clean All in all, great location, ambiance and value.

Reviewed on Dec 7, 2025

The Key West Hotel

Key West Historic District

$1,553

per person

Feb 8 - Feb 12

found 3 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Room was great and clean.

Reviewed on Dec 7, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,320

per person

Feb 8 - Feb 12

found 3 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Private Beach is Amazing !!

Reviewed on Dec 7, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

Top Pet-friendly Florida Keys Hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

7 min drive from Duval Street

This family-friendly, oceanfront hotel welcomes four-legged friends (fees apply) and offers pet-friendly amenities, like a dog park. While you're here, hike ...

8/10 Very Good! (1,750 reviews)

Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on Dec 5, 2025

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

10 min drive from Duval Street

Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this luxury, oceanfront hotel.

8.8/10 Excellent! (1,747 reviews)

Very nice clean and big room. Great view over the pools and harbor.

Reviewed on Dec 4, 2025

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

4 min drive from Duval Street

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! (1,782 reviews)

Rooms clean and smelled good Staff was great! Loved the pool

Reviewed on Dec 5, 2025

See all 8,379 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.