20 Pet Friendly Hotels in Key West, Florida | North Roosevelt to Boulevard Picks

1. Parrot Key Hotel & Villas

The Vibe

Parrot Key feels like a tropical village with winding pathways, lush landscaping, and free-roaming chickens that guests love. It’s oceanfront on Florida Bay, not beachfront, but the shuttle runs you to their local beach spot in five minutes flat.

What You Actually Get

Rooms are roomy and clean — the 8.8 cleanliness score backs that up. You get free WiFi (rated 8.6), on-site fitness center, private parking, and a good breakfast. Dogs are allowed on request with potential charges. The front door property-wide smoking ban (with a $250/day fine if broken) keeps the air fresh for your pet. Note: groups booking 5+ rooms trigger different policies, so read the fine print if you’re traveling with a pack.

Choose this if: You want resort amenities (pools, restaurant, free shuttle) with a pet-friendly green light.

2. The Capitana Key West

The Vibe

The Capitana is immaculate — guests rave about how spotless it is inside and out. It sits away from the Duval Street chaos but within an easy drive. Their own beach area for sunbathing means you can bring your dog to the sand without fighting for a towel.

What You Actually Get

With a 9.5 cleanliness and 9.5 comfort score, this is the cleanest hotel on our list. You get free private parking (major win in Key West), an outdoor pool, fitness center, and a restaurant open for breakfast and lunch. Pets are allowed with potential charges. There’s a coin-operated laundry on-site — useful if your dog rolls in something questionable. The free WiFi (7.6) is slower than the resort standard, so don’t plan on streaming a movie marathon.

Choose this if: You rank spotless rooms over everything — your nose and your pet’s will thank you.

3. Wicker Guesthouse

The Vibe

Wicker sits smack on Duval Street — the heartbeat of Key West. One block from Hemingway House, it blends a large tropical garden with a small pool. The staff score 8.9, and guests call the beds very comfortable. It’s loud in the best way if you want proximity to everything.

What You Actually Get

Location is the star here at 9.4. Rooms are basic but clean (8.1), with comfort at 8.2. Free on-site and public street parking (keys left with front desk) keeps it practical. Pets allowed on request with charges. The check-in window closes at 9 PM, so plan your flight accordingly. Extra beds available at $20/night for families — useful if your kid doesn’t want to share with the dog.

Choose this if: You want to step out your door and be on the main strip — pet-friendly and people-friendly.

4. The Palms Hotel

The Vibe

The Palms is quaint and cozy — guests are genuinely surprised the free breakfast goes beyond basics. Heated pool year-round means you can swim even in January. WiFi scores 8.8, so your remote work or pet photo uploads won’t lag.

What You Actually Get

All rooms come with mini fridges — stash your dog’s food or your own cold drinks. Comfort and cleanliness both hit 8.9 and 8.8, respectively. Pets are allowed with charges. Free breakfast includes Colombian coffee, three juice types, and yogurt. Limited on-site parking is first-come, first-served, with free street parking as backup. Guests must be 21+ to check in.

Choose this if: You want a quiet, cozy stay with a heated pool and a free breakfast that punches above its weight.

5. Douglas House Adult Only

The Vibe

Douglas House is adult-only, meaning no screaming kids — just the occasional happy bark. Location scores 9.7, staff 9.3, cleanliness 9.3. The neighborhood is quiet, yet Duval is a short walk. This is for couples who want romantic Key West with their dog.

What You Actually Get

Pets are allowed with charges, but only select rooms accommodate them — you must contact Douglas House directly for details. The property is not a party spot and actively discourages group bookings (max 2 rooms per group). All rooms have private bathrooms. Check-in closes at 8 PM sharp. Free WiFi scores 8.9. No kids allowed — this is strictly 18+.

Choose this if: You’re a couple traveling without kids and want a peaceful, adult-only vibe that welcomes your dog.

6. Winslow’s Bungalows – Key West Historic Inns

The Vibe

Three pools. Yes, three. Winslow’s feels like a private resort even though it’s walking distance to downtown. Staff hits 9.0, and guests love the free breakfast buffet and evening welcome drinks. No elevator, so pack light if you’re on the second floor.

What You Actually Get

Pets are allowed with charges. Free continental breakfast and coffee/tea service included. Parking costs $20 plus tax per day. The resort fee also includes snorkel kit, boating towels, and a boozy welcome. WiFi is 7.8 — solid but not blazing. The property is in a building with no elevator, which matters if your dog can’t do stairs or you have heavy luggage.

Choose this if: You want resort-style amenities (multiple pools, free breakfast) with downtown walkability and pet acceptance.

7. Oceans Edge Key West

The Vibe

Six swimming pools and a waterfront bar — Oceans Edge is a full-on resort experience. Cleanliness scores 9.1, comfort 9.0, and guests love the modern, cozy rooms. Free bikes, paddleboards, and kayaks are included in the daily resort fee. Dogs allowed with charges.

What You Actually Get

The daily resort fee covers two hours of bike, paddleboard, and kayak rentals — great if your dog enjoys a slow paddle. WiFi scores a stellar 9.2. Restaurant on-site serves breakfast, lunch, and dinner. Elevator access to upper floors available. Guests must be 25+ to check in without a parent or guardian. The resort fee is charged with the deposit and is non-refundable if you cancel.

Choose this if: You want an all-in resort feel with water views and enough pools to swim in a different one every day.

8. Courtney’s Place Historic Cottages & Inns

The Vibe

Courtney’s Place is a collection of historic cottages, not a standard hotel. Location scores a massive 9.7 — one minute on foot to Duval. Comfort and cleanliness both hit 9.2. Guests rave about the comfy beds and the cottage setup that gives you space to spread out with your pet.

What You Actually Get

Cottages come with kitchens (stove tops), making this a top pick for extended stays with pets. C4 family cottage has two queen bedrooms plus a loft with a queen, two twins, and a full-size bed — sleeps big families. Pets allowed on request with charges. Free private parking on-site. Check-in closes at 5 PM, so coordinate your flight. Guests under 25 need a parent or guardian to check in.

Choose this if: You need a kitchen and separate bedrooms for your family — pet-friendly and walking distance to everything.

9. Havana Cabana at Key West

The Vibe

Havana Cabana has a strong island vibe — pool and bar in the middle of a courtyard, rooms arranged around it. Guests say it’s quiet despite the central layout. Free shuttle to Duval and Mallory Square runs hourly. Staff scores 8.6, WiFi scores 9.3.

What You Actually Get

Pets are allowed with charges. Free parking included (rare in Key West). Free shuttle to downtown runs every hour — register at the front desk. Breakfast available for €14. Airport shuttle also available. Guests must be 21+ to check in. Groups booking 5+ rooms trigger different policies. The resort fee covers WiFi and shuttle service.

Choose this if: You want budget-friendly rates, free parking, and a free shuttle to the action, with your pet along for the ride.

10. Old Town Manor

The Vibe

Old Town Manor is adult-only (no kids), pet-friendly (ALL breeds and sizes welcome), and smoke-free. Location hits 9.5, comfort 9.2, and guests love the stylish, high-quality furnishings. No pool, but you can use the one at their sister property, Rose Lane Villas, less than a minute away.

What You Actually Get

This is the most inclusive pet policy on the list — no breed restrictions, no size limits, “we love them all as long as they are housebroken.” Parking is available for an additional fee with limited spaces. Check-in closes at 7 PM. Staff speak English and Spanish. Simonton Beach is 4 blocks away, Fort Zachary Taylor State Park is 1 mile. No children allowed, so it’s quiet.

Choose this if: You have a large or “restricted breed” dog — this is the most welcoming pet policy in Key West.

11. Hilton Garden Inn Key West / The Keys Collection

The Vibe

This Hilton Garden Inn delivers predictable quality — comfortable rooms, friendly staff (Marcello gets namedropped in reviews), and a to-go breakfast setup. It’s close to the airport (2 minutes drive) and 10 minutes from Duval by car. Good for a quick stopover with your pet.

What You Actually Get

Pets allowed with charges. On-site parking (covered option available, extra for oversized vehicles). Outdoor pool, restaurant, fitness center, and balconies in some rooms. Free WiFi scores 8.8. No jacuzzi suites, but there’s a jacuzzi at the pool. Shuttle service to Old Town requires advance reservation and a boarding pass from the front desk. Breakfast is served as a to-go bag.

Choose this if: You want brand reliability, covered parking, and easy airport access with your pet.

12. Fairfield Inn & Suites by Marriott Key West

The Vibe

Fairfield Inn is a solid Marriott property with a large outdoor pool and poolside cabanas. Guests praise the friendly staff and helpful concierge. The location is central enough to reach both downtown and Smathers Beach easily via their two shuttles.

What You Actually Get

Pets allowed with charges. Two shuttle services included: one to Downtown and one to Smathers Beach — full details at check-in. Free hot breakfast. Private parking available. Outdoor pool with cabanas. Fitness center on-site. No rollaway beds available currently. Guests must be 21+ to check in without parent or guardian.

Choose this if: You want a reliable Marriott stay with free shuttles to both the beach and downtown for pet-friendly exploring.

13. Lighthouse Hotel – Key West Historic Inns

The Vibe

Lighthouse Hotel sits opposite the Ernest Hemingway Home and Museum and the Keeper’s Quarters Museum. It’s quaint, quiet, and convenient — guests rave about the excellent breakfast buffet and the friendly staff who go above and beyond. Location is a standout at 9.5.

What You Actually Get

Pets allowed with charges. All rooms have TVs and mini fridges. Parking is off-site in a private lot 5 minutes walk from the property, costing $20/night. Check-in parking is available at the rear on Terry Lane. Free WiFi scores 7.3. Good breakfast buffet included. Groups booking 4+ rooms trigger different policies.

Choose this if: You want to be in the historic heart of Key West, opposite a major landmark, with a great breakfast to start your day.

14. Pier House Resort & Spa

The Vibe

Pier House is the only full-service resort with a private beach right on Duval Street. Location scores 9.7. It’s pricey, but guests say the quality justifies it — fresh food, excellent service, and you’re steps from sunset celebrations at Mallory Square.

What You Actually Get

Pets allowed with charges. Private beach area, three restaurants, full-service spa, and fitness center. Rooms have tea/coffee makers but no microwaves. Fridges available. The property is 100% non-smoking (balconies included). On-site parking available for guests. WiFi scores 8.5. This is a splurge — if you’re looking for value, this isn’t it, but for quality, it delivers.

Choose this if: You want the full Key West package — private beach, spa, and a prime location — and don’t mind paying for it.

15. Hyatt Centric Key West Resort & Spa

The Vibe

Hyatt Centric sits on the waterfront with on-site spa and fitness center. Location hits 9.4. Guests rave about the staff and the pool bar food. The private beach is on the property, a short walk from your room. It’s polished and upscale.

What You Actually Get

Pets are allowed on request, but you must provide current proof of vaccinations at check-in. There’s a $150 pet cleaning fee. The property is non-smoking. WiFi scores 9.4 — strong. Breakfast costs €44 if not included in your package. Daily service fee of $65.25 applies. Two restaurants, private parking, and balconies in some rooms. This is the most thorough pet policy in terms of health documentation.

Choose this if: You want a waterfront resort with a strict but fair pet policy that prioritizes health and safety.

16. Fitch Lodge – Key West Historic Inns

The Vibe

Fitch Lodge is a smaller boutique property where manager Lee gets personal shoutouts from guests. The complimentary afternoon drinks are a hit. Rooms are clean (8.5) and comfortable (8.6). Location scores 8.8, and it’s popular with solo travelers.

What You Actually Get

Pets allowed with charges. No parking on-site — the city parking garage costs $32/night. No elevator, so request a ground floor if stairs are an issue. Resort fee includes personalized concierge services. Deposit is charged immediately at booking. WiFi scores 6.9 — the weakest on this list. The property is 100% smoke-free.

Choose this if: You want a small, friendly property with complimentary drinks and clean rooms, and don’t mind paying for parking.

17. The Garden House

The Vibe

The Garden House is a small guesthouse with a massive personality — “Sammy from Miami” is the host everyone mentions. Location is 9.5, staff 9.3, and the breakfast gets called “amazing” by guests. It’s walking distance to the Key West Express ferry terminal.

What You Actually Get

Pets allowed with charges. Private parking available on-site. All rooms have private bathrooms. Breakfast is included and highly praised. WiFi scores 8.9. Guests must be 25+ to check in without a parent or guardian. No children allowed — adult-only property. Cozy King rooms have king-sized beds (not queens, despite the name confusion).

Choose this if: You want a personal, host-driven experience with amazing breakfast and a quiet garden setting.

18. Ridley House – Key West Historic Inns

The Vibe

Ridley House is a boutique hotel with serious style — sangria happy hours and a great breakfast setup. Location scores 9.7, comfort 9.0. Staff hits 9.1. Guests say the beds are very comfortable and the property is “really lovely.”

What You Actually Get

Pets allowed with charges. No on-site parking — a pay lot around the corner with daily rates. No elevator. WiFi scores 9.3. Continental breakfast included. Each room is unique (the pictures are accurate to the specific room you book). Resort fee includes concierge services. Deposit charged immediately at booking.

Choose this if: You want a unique, beautifully designed room with a stellar location and a free sangria hour to kick off your evening.

19. Ella’s Cottages – Key West Historic Inns

The Vibe

Ella’s Cottages is a boutique collection of cottages in Old Town, two minutes from Duval. Guests rave about the location (9.6), the exceptionally welcoming staff (9.3), and the cozy feel. Comfort scores 9.1 — beds and pillows get special mentions. It feels like staying at a friend’s well-appointed vacation home.

What You Actually Get

Pets are allowed — the property says “we are completely pet friendly.” Parking costs $20 plus tax per night. Heated outdoor pool. Daily Guest Amenity Fee covers continental breakfast (8-10 AM), welcome beverages, afternoon refresher, concierge, WiFi, Turkish robes, and yoga mats. WiFi scores 9.5 — excellent for remote work. Staff available from 7:30 AM to 10 PM, with night managers after hours.

Choose this if: You want a cozy cottage with a heated pool, exceptional staff, and a pet policy that actually says “completely pet friendly.”

20. Kona Kai Oasis

The Vibe

Kona Kai Oasis is an intimate, budget-friendly B&B in Old Town. It’s no-frills but practical. Free parking, free WiFi, and a pool. The lowest pet fee on this list at $20 per night plus tax makes it the cheapest option if you’re traveling with a dog on a budget.

What You Actually Get

Pets allowed on request — you must advise at time of booking. Pet fee is $20 per night plus tax. Free private parking on-site. All rooms are non-smoking. Extra bed available for $20 per person per night for adults 18+. Outdoor pool and terrace. Breakfast not included. Check-in available until midnight, which is the latest window on this list. No children allowed.

Choose this if: You’re on a budget and need the cheapest pet fee in Key West with free parking and a late check-in window.

These pet friendly hotels in Key West, Florida cover every budget and style — whether you’re looking for resort luxury or a cozy cottage, your dog is welcome.