13 Charming Guest Houses in Key West (2026)

Key West is home to an array of delightful guest houses that offer a unique and relaxed stay. Whether set in lush tropical gardens or quaint historic buildings, you'll find heaps of character and charm here. From cosy cottages to adults-only retreats, many feature beautiful outdoor spaces, inviting pools and sociable happy hours. And if you can drag yourself away from your comfortable base, you'll discover easy access to the island's top attractions.

For an adults-only escape

• Choose Seascape Tropical Inn for an adults-only oasis, with just six pretty rooms featuring wicker furniture, unique artwork and brightly coloured walls. The garden is a delight, with its heated pool and relaxing sun deck, while nearby you can discover Duval Street with its restaurants, shops, vibrant scenery and history.
• L'Habitation Hotel is a lovely historic B&B set close to restaurants, nightlife and cultural attractions. This adults-only retreat features four-poster beds, artworks, large walk-in showers and a relaxing tropical rooftop terrace. Guests also have access to a host of water sports from jetskiing to parasailing.

• The name says it all, The Paradise Inn is the perfect pick for a peaceful, adults-only stay. The stylish and simple rooms, painted in calming whites and nudes, are flooded with natural light. There's also an outdoor hot tub, fountain-fed pool and a wine and cheese happy hour.
• Just off the famous Duval Street, Marrero's Guest Mansion is another intimate adults' retreat. Expect tropical and bright rooms with coastal touches, air-con and a gorgeous saltwater pool. Enjoy a daily happy hour, plus a large front porch looking across the lush palm-filled garden.

For character and charm

• Set in a restored Victorian mansion with a turret, The Artist House offers seven elegant rooms with high ceilings and ornate woodwork, retaining the original character. Outside is equally impressive with an inviting pool, pretty garden and a lovely front porch from which you can watch the world go by.
• Nestled in the heart of the Old Town, the aptly named Old Town Manor features rooms with private outdoor garden decks. Built in 1886, it retains its historic charm but offers modern convenience too with large bathrooms boasting walk-in rainfall showers. Enjoy an organic breakfast served amidst the lush gardens. 

• Key West B&B is a chic little haven with original local artworks and a sophisticated grown-up vibe, where many of the rooms offer private decks overlooking the Old Town and the gardens. Unwind in the hammock on the porch, take a dip in the pool and enjoy a homemade breakfast on the terrace.
• The Mermaid and the Alligator is another artsy stay with tropical decor, four-poster beds and luxe linen. The B&B's concierge can organise snorkelling and boat tours, plus there are bikes available to hire, so you can spend a day exploring Key West on two wheels. Smathers Beach is just a five minute ride away. 

For an inviting pool

• Southernmost House is an old Victorian property in a fantastic location, just steps from the shore yet close to top-tier eateries and art galleries. Rooms have a romantic feel, with four-poster beds and fabulous sea views, but the highlight is the large pool surrounded by relaxing sun beds.
• Simonton Court Historic Inn & Cottages is a stylish choice, with its tropical rooms with private decks and bathrooms featuring rainfall showers. The verdant gardens are gorgeous and boast no less than four pools. If you want to venture further afield, the guesthouse can arrange a wide range of water sports.

• For an idyllic escape with more of a contemporary feel, Ella's Cottages - Key West Historic Inns hits the mark. Set in a lush tropical garden, you'll discover sleek interiors, in-room yoga mats, private patios and large rainfall showers. The pool, cloistered by banana palms, is a delight.
• Rooms are classical and coastal at The Conch House Heritage Inn. Think ceiling fans, traditional antique furnishings, artworks and large bathrooms with walk-in showers. This elegant inn offers poolside breakfasts with freshly squeezed juices and champagne mimosas. The perfect way to start the day.

For a group getaway

• A lovingly restored historic hotel, Coco Plum Inn can accommodate one group with its three, individual, side-by-side rooms that share a common space. The lush garden is a great spot to relax with its ferns and palms, while there's a heated outdoor pool for some fun in the sun.

Still not sure? 

• Browse through our full list of accommodation options in Key West,
• Refine your search to include our recommendations for The 10 Best Hotels in Key West for Couples or The Best Hotels in Key West Historic District,
• Alternatively, contact one of our friendly Gurus for personalised advice.