Stay at Winslow’s Bungalows

Indulge in the luxe comfort of your king bed and immerse yourself in the brightly lit, calming vibe of this room. Complete with everything you need for an unforgettable Key West stay.

Step outside onto your 35-square-foot patio to bask in the Florida sunshine. Inside, sink into the plush comfort of a king bed and indulge in luxe bath amenities.

Welcome to your home away from home in the heart of Key West! Our largest suite boasts 600 square feet of comfort. Enjoy a separate living area, a full bath and shower, and a spacious balcony for a truly resort-like experience.

Get the most out of your Key West getaway and enjoy a plush queen bed, timelessly charming island-chic decor, and luxurious bath amenities.

An ideal stay for up to four guests. Two queen beds offer plenty of space for your small group to unwind in style.

Experience the carefree vibes of Key West in this spacious and premium room, featuring a plush king bed and soaking tub for ultimate relaxation.

Everything you need for a perfect Key West getaway. A patio for enjoying the sunshine, a sofa bed for extra lounge space, and a king bed for restful nights before your next adventure.

A 30-square-foot balcony provides the perfect place to bask in the Key West Sunshine and enjoy an afternoon cocktail. Inside, find eclectic comfort and a plush king bed.

All the inviting and stylish decor you expect from Winslow’s Bungalows, along with thoughtful accessible touches including a roll-in shower to ensure your safety and comfort.

Spacious and stylish, with two queen beds offering plenty of room for group getaways and family vacations. Accessible touches provide comfort and safety for all guests. Fitted with a gated patio poolside offering all of the Key West sunshine and splashes.

Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind and relax after a day exploring nearby Duval Street.

Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax on comfortable outdoor seating after a day exploring Duval Street.

Step back in time and immerse yourself in the charm of this Victorian treasure, beautifully adorned with original pine walls. Enjoy your morning coffee or an evening drink on your private wrap-around balcony.

Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax on comfortable outdoor seating after a day exploring Duval Street.

Your private Key West sanctuary awaits. Sink into the charm of lush gardens, a gated patio, a basket chair to enjoy the salt air and sunshine. Unwind by day, sink into a king bed by night.

Immerse yourself in the Key West lifestyle with easy access to our sparkling pool. Cane furniture creates an island ambiance, seamlessly blending your private patio with your luxurious room.

Enjoy charming Victorian architecture in an accessible oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax outdoors after a day exploring Duval Street.

Live like a local in authentic Key West conch homes brimming with vibrant colors. Cane furnishings create a warm, carefree bohemian ambiance, immersing you in island life.

Wake up to views of our sparkling pool and the iconic Basilica of St. Mary Star of the Sea. Enjoy an airy, light-filled room and indulge in your spacious soaking tub. Bask in the Key West sunshine on your patio.