Key West has a reputation as a laid-back, dog-friendly destination — and it’s mostly true. You’ll see dogs at restaurants, bars, and even wandering Duval Street with their owners. But finding a hotel that actually welcomes bigger dogs? That’s trickier than you’d expect.

I spent a few hours researching this one because most of the “dog-friendly” hotels in Key West have frustrating weight limits. The boutique inns cap out at 20-30 lbs. The Curio Collection properties (The Reach, Casa Marina) only allow dogs up to 25 lbs. Even Margaritaville maxes out at 50 lbs.

If you’ve got a bigger dog, here’s what actually works.

My Pick: DoubleTree Resort by Hilton Grand Key - Key West

The DoubleTree Grand Key is one of the only Hilton properties in Key West with a 75 lb weight limit. Most of the others cap out at 25-50 lbs. For reference, Ansel is 70 lbs — he’d fit here but get rejected at most of the boutique options.

The hotel is on the quieter side of the island, about 5 minutes from the airport. It’s not walking distance to Duval Street, but they run a free shuttle to Old Town and the beach. If you have a car, everything is 10-15 minutes away.

The Pet Policy Details

• 75 lb weight limit — One of the highest limits in Key West
• $75 per night pet fee — On the higher side, but standard for Key West
• 2 pets max — Dogs or cats allowed
• Pets cannot be left unattended — You’ll need a plan for any activities where dogs aren’t allowed
• No breed restrictions — At least not at the corporate level

The hotel has a resort feel with a zero-entry pool, tiki bar, and on-site restaurant (Palm Haven). The resort fee includes shuttle service, airport pickup, and beach club access. Dogs aren’t allowed at the pool, which is standard — plan around it.

How to Book It Free

The DoubleTree Grand Key typically runs around 60,000-80,000 Hilton Honors points per night, depending on season. Key West is expensive no matter how you slice it — cash rates often hit $300-500+ per night, especially during winter season.

The math:

• The Hilton Surpass card has a 155,000 point sign-up bonus
• That’s 2-3 free nights at this property
• Book 5 nights and the 5th night is free — built-in 20% discount
• You’d only pay the $75/night pet fee out of pocket

The FlyerTalk forums have good intel on this property — several people mentioned using points here over Christmas when cash rates were $1,000+ per night. At that point, even 70-80k points per night is solid value.

👉 Full breakdown of Hilton cards

What to Do With Your Dog

Key West is genuinely one of the more dog-friendly destinations in Florida. Here’s what’s actually available:

Dog Beach

Key West has a real, designated off-leash dog beach. It’s small — maybe 20 feet wide — but it’s the only spot on the island where your dog can legally swim and run off-leash.

The beach is right next to Louie’s Backyard, an upscale waterfront restaurant. After your dog swims, you can grab a drink at their Afterdeck Bar — dogs are welcome on the patio until 5pm.

Heads up: The beach is rocky and can be slippery. Bring water shoes if you plan to wade in with your dog. Some reviews mention seaweed and debris — it’s not a pristine beach, but it’s the only off-leash option.

Higgs Beach Dog Park

If your dog prefers grass over sand, Higgs Beach Dog Park is the better option. It’s a fenced park with separate areas for large and small dogs, shade structures, water fountains, and ocean views.

The park is about 15 minutes from the DoubleTree. After letting your dog run, you can walk over to White Street Pier for ocean views.

Dog-Friendly Restaurants & Bars

Key West has a bar-and-patio culture that works well for dogs. Most places with outdoor seating are dog-friendly — staff will usually bring out a water bowl without you asking.

The Standouts

Schooner Wharf Bar — At the Historic Seaport, this is Old Key West vibes with live music, fresh seafood, and plenty of outdoor space. Dogs welcome. Their T-shirts literally have dogs on them.

Blue Heaven — Famous for breakfast, with an open-air garden setting. Roosters and chickens roam the property (fair warning for reactive dogs). Live music, laid-back atmosphere.

Hog’s Breath Saloon — Classic Key West bar at Front and Duval. Large outdoor patio, live music, dog-friendly.

Island Dogs Bar — The name says it all. Located in Old Town, they welcome dogs on their outdoor patio and have a relaxed atmosphere with live music.

Louie’s Backyard (Afterdeck Bar) — Right next to Dog Beach. The Afterdeck is drinks-only but welcomes dogs until 5pm. Great views.

Other Good Options

• Smokin’ Tuna Saloon — Off Duval Street, courtyard with live music
• Half Shell Raw Bar — Waterfront seafood, outdoor seating
• Banana Cafe — French bistro with dog-friendly patio
• Geiger Key Marina Fish Camp — Worth the drive to Stock Island, waterfront with a dog menu

Dog-Friendly Attractions

Key West Tropical Forest & Botanical Garden

15 acres of native plants, walking trails, and picnic areas. Leashed dogs welcome. One of the only truly “natural” spots on the island.

Location: 5210 College Road — about 5 minutes from the DoubleTree

Mallory Square Sunset Celebration

Every evening, crowds gather at Mallory Square to watch the sunset over the Gulf. Street performers, artists, food vendors. Leashed dogs are welcome — just be prepared for crowds and noise.

Key West Aquarium

This surprised me: the Key West Aquarium actually allows leashed dogs inside. It’s a small historic aquarium in Mallory Square with touch tanks and marine life exhibits.

Walking Tours

Key West is walkable and most of Old Town is accessible on foot with a leashed dog. You can stroll past the Hemingway House (dogs allowed on the grounds, but be aware of the resident cats), check out Duval Street, and explore the historic district.

Dog Daycare Options

If you want to do something where dogs aren’t allowed — like snorkeling, the Dry Tortugas ferry, or a long day at the pool — you’ll need daycare. Options are limited in Key West:

Abigail & Stitch Pet Resort — The main boarding/daycare facility in Key West. Affiliated with All Animal Clinic, so a vet is nearby if needed.

Rover sitters — There are about 30 pet sitters on Rover in Key West. This can be a good option if your dog doesn’t do well in kennel environments.

Book ahead during busy season — Key West is a small island and daycare spots fill up.

Quick Reference

Other Options I Considered

If the DoubleTree doesn’t work for your dates, here are the alternatives:

Hampton Inn Key West — Also bookable with Hilton points, free breakfast included. Pet-friendly but I couldn’t confirm the exact weight limit. Worth calling to check.

Havana Cabana — Independent resort with a $75/day first dog fee. Pets allowed in lobby, tiki hut, shuttle, and pool bar (but not pool). Not bookable with points.

The Perry Hotel & Marina — On Stock Island, slightly outside Key West proper. Good reviews for dogs, waterfront location. Check their pet policy for weight limits.

For smaller dogs (under 25 lbs), The Reach Key West and Casa Marina are beautiful Curio Collection properties right on the beach — but the weight limit rules out most medium and large dogs.

The Bottom Line

Key West is legitimately dog-friendly once you’re there — the restaurants, bars, and even some attractions welcome dogs. The challenge is finding a hotel that accommodates bigger dogs without crazy restrictions.

The DoubleTree Grand Key hits the sweet spot: 75 lb weight limit, Hilton points redemption, and a free shuttle to get around the island. It’s not beachfront, but with Dog Beach and Higgs Beach Dog Park both a short drive away, your pup will still get plenty of sand and water time.

Just budget for the $75/night pet fee and book daycare in advance if you need it.

Haven’t been to Key West with your dog yet but this is on my list. If you’ve stayed at the DoubleTree (or found a better option), I’d love to hear about it — leave your pawprint or email me at woof@thepointspup.com.

This is part of my Destinations series — one hotel pick per city, plus how to book it free with points.

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