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Cottage

Key West Cottage Rentals

Stay in a charming Key West cottage rental. Key West is famous for its historic architecture where cottages are tucked away near Duval Street, at the center of Old Town. Our Key West cottages with pools provide a special mix of charm and modern comfort. Many Key West cottages have been fully renovated with lush backyards, high speed wifi, and lounge areas, while also maintaining their unique qualities like cathedral ceilings, French doors, and spiral staircases. 

Book a Classic Cottage on Key West!
 

Age 12 and under.

List View

Ann Street Cottage

House
One Bedroom
1.5 Bathrooms

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.

Bali Hideaway

Studio/Efficiency
Bedrooms 0.5
One Bathroom

Perfect for two, this Bali-style studio cottage has it all:  comfort, privacy and location.

Colony Calypso

House
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography.

Pete's East Cottage

House
Bedrooms 2
One Bathroom

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.

Pete's West Cottage

House
Bedrooms 2
One Bathroom

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall. 

Map View