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Pet Friendly

Age 12 and under.

List View

Angela Cottage

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a great central location to get to the Historic seaport or new town.

Catherine House

House
Bedrooms 2
2 Bathrooms

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.

Havana Lane

House
Bedrooms 2
2 Bathrooms

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends.

Sanctuary on Simonton

Condo
Bedrooms 2.5
3 Bathrooms

28 DAY MINIMUM- Dogs allowed, with restrictions

Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway.

South St. Cottage

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  South Street Cottage is a bright and sunny "pool home" situated on a quiet street in the coveted and quiet Casa Marina district of Key West.

Ashe Splashe

House
Bedrooms 3
3 Bathrooms

28 DAY MINIMUM RENTAL

From the owners of South of Frances, here is another beautiful, historic restoration project. This lovingly restored home is ready for guests following a complete redo! The attention to detail and master craftsmanship can be seen everywhere in this beautiful home.

Elizabeth Retreat

House
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  Want to saunter through the historic streets of Key West and live like a local in a quiet, Old Town residential neighborhood? Look no further than Elizabeth Retreat.

Mango Menagerie

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental: Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm.

Packer Retreat

House
Bedrooms 3
3.5 Bathrooms

28 Day Minimum rental:  Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district.

Villa Paradiso

House
Bedrooms 3
3 Bathrooms

This mid-town Key West home is beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics.

Map View