Top Pet-friendly vacation packages 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

$694

per person

Mar 30 - Apr 2

found 20 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Beautiful relaxing place! The grounds were spotless! The staff was so accommodating! Our room was stocked with supplies that every traveler could need.

Reviewed on Jan 24, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$909

per person

Mar 30 - Apr 2

found 20 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Nice, spacious suite with an amazing waterfront view. The staff was incredibly warm and welcoming. Beautiful heated pool; I didn’t want to get out. The drinks at the tiki bar could’ve been improved. Lovely beachfront and walkable to several restaurants.

Reviewed on Jan 20, 2026

Islander Resort

Matecumbe

Save 100% on your flight

$849

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

Very expensive resort. Room Service bad, room small and cost a lots, food good but expensive, staff ok, but could be better.

Reviewed on Jan 20, 2026

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$1,377

per person

Mar 30 - Apr 2

found 11 hours ago

Roundtrip non-stop flight included

Akron (CAK) to Key West (EYW)

8.4/10 Very Good! (1,001 reviews)

Food was great! Jose our server was excellent!

Reviewed on Jan 27, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,359

per person

Mar 30 - Apr 2

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Room was not ready for 1/2 hour past check in time.

Reviewed on Jan 25, 2026

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3 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

$694

per person

Mar 30 - Apr 2

found 20 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Beautiful relaxing place! The grounds were spotless! The staff was so accommodating! Our room was stocked with supplies that every traveler could need.

Reviewed on Jan 24, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$909

per person

Mar 30 - Apr 2

found 20 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Nice, spacious suite with an amazing waterfront view. The staff was incredibly warm and welcoming. Beautiful heated pool; I didn’t want to get out. The drinks at the tiki bar could’ve been improved. Lovely beachfront and walkable to several restaurants.

Reviewed on Jan 20, 2026

Islander Resort

Matecumbe

$1,218

per person

Feb 27 - Mar 2

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

Very expensive resort. Room Service bad, room small and cost a lots, food good but expensive, staff ok, but could be better.

Reviewed on Jan 20, 2026

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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

$982

per person

Mar 30 - Apr 3

found 15 hours ago

Roundtrip flight included

Hartford (BDL) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Beautiful relaxing place! The grounds were spotless! The staff was so accommodating! Our room was stocked with supplies that every traveler could need.

Reviewed on Jan 24, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,149

per person

Feb 27 - Mar 3

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Nice, spacious suite with an amazing waterfront view. The staff was incredibly warm and welcoming. Beautiful heated pool; I didn’t want to get out. The drinks at the tiki bar could’ve been improved. Lovely beachfront and walkable to several restaurants.

Reviewed on Jan 20, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,198

per person

Feb 27 - Mar 3

found 1 day ago

Roundtrip non-stop flight included

Albany (ALB) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Great location, very clean, and great staff

Reviewed on Jan 18, 2026

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Top Pet-friendly Florida Keys Hotels

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

5 min drive from Duval Street

Hiking and biking trails are ready for you to explore near this waterfront hotel, where dogs and cats can stay for an additional fee.

9/10 Wonderful! (1,251 reviews)

Lovely room!

Reviewed on Jan 24, 2026

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! (1,786 reviews)

The room was clean and bright!

Reviewed on Jan 24, 2026

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! (1,787 reviews)

Rooms and resort were very clean. The staff was exceptionally friendly and were so accommodating!

Reviewed on Jan 23, 2026

See all 8,417 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.