Florida Keys Pet-friendly Vacations

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Top Pet-friendly vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas

La Siesta Resort & Villas

Matecumbe
$668
per person
Oct 31 - Nov 3
found 10 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
8.6/10 Excellent! (1,003 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,239
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Tortoises on property blew me away! Along with beautiful pool area. 4 poster king bed. Huge bathroom with spa tub and rain shower. Every member of the staff was super friendly and accommodating. Awesome poolside bar with live music during happy hour. Looking forward to our next trip here.....which we've already booked. Wish I would've found this place years ago.

Reviewed on Aug 22, 2026

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

Key West Historic District
$1,144
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9/10 Wonderful! (1,016 reviews)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

Old Town Key West
$1,399
per person
Oct 25 - Oct 29
found 12 hours ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Key West (EYW)
8.6/10 Excellent! (1,005 reviews)
Close to Duval Street. Property was not worth the price. Have stayed in much nicer properties for less. Cleaning team did not restock items. Minor item but toilet paper was AWFUL!

Reviewed on Aug 23, 2026

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

$688
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
8.4/10 Very Good! (1,066 reviews)
Joe at the front desk was very helpful. We did have a few issues with housekeeping and being able to get into our room. On four separate occasions, we had to come and have someone readjust the lock on our door because our keys did not work. We did enjoy the complementary coffee each morning.

Reviewed on Aug 24, 2026

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3 Night Pet-friendly vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

$688
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
8.4/10 Very Good! (1,066 reviews)
Joe at the front desk was very helpful. We did have a few issues with housekeeping and being able to get into our room. On four separate occasions, we had to come and have someone readjust the lock on our door because our keys did not work. We did enjoy the complementary coffee each morning.

Reviewed on Aug 24, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,239
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Tortoises on property blew me away! Along with beautiful pool area. 4 poster king bed. Huge bathroom with spa tub and rain shower. Every member of the staff was super friendly and accommodating. Awesome poolside bar with live music during happy hour. Looking forward to our next trip here.....which we've already booked. Wish I would've found this place years ago.

Reviewed on Aug 22, 2026

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

Key West Historic District
$1,144
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9/10 Wonderful! (1,016 reviews)
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4 Night Pet-friendly vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Bayside Inn Key Largo

Bayside Inn Key Largo

$474
per person
Oct 28 - Nov 1
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.6/10 Excellent! (1,826 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,651
per person
Oct 24 - Oct 28
found 12 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,608
per person
Oct 24 - Oct 28
found 12 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Tortoises on property blew me away! Along with beautiful pool area. 4 poster king bed. Huge bathroom with spa tub and rain shower. Every member of the staff was super friendly and accommodating. Awesome poolside bar with live music during happy hour. Looking forward to our next trip here.....which we've already booked. Wish I would've found this place years ago.

Reviewed on Aug 22, 2026

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Top Pet-friendly Florida Keys Hotels

Havana Cabana at Key West

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL
  • 6 min drive from Duval Street
Four-legged friends will appreciate the amenities, such as food and water bowls, during their stay (fees apply) at this pet-friendly hotel.
9/10 Wonderful! (1,866 reviews)
"Beautiful place I will go back"

Reviewed on Aug 24, 2026

Havana Cabana at Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
  • 4 min drive from Duval Street
With pet-friendly amenities like food and water bowls, this family-friendly, oceanfront hotel welcomes dogs (fees apply). Don't forget to check out nearby Bayview ...
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

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 ...
Blue Flamingo Resort Key West
See all 8,267 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.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Florida Keys

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.