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Vacation rentals in Cudjoe Bay

Find and book unique accommodations on Airbnb

Popular amenities for Cudjoe Bay vacation rentals

Free parking on premises

Air conditioning

Homes with more space

Top guest favorite

A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.

Home in Cudjoe Key

4.98 out of 5 average rating, 56 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

Tiny home in Big Pine Key

4.93 out of 5 average rating, 73 reviews

Cottage 30 min from Key West, free parking, pool

Top guest favorite

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

Cottage in Cudjoe Key

4.99 out of 5 average rating, 92 reviews

Beautiful Cottage & Amenities in Gated Community

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

Home in Cudjoe Key

4.86 out of 5 average rating, 69 reviews

Cozy 2 br/2 bath home in Cudjoe