
Settle into a quieter side of Key West.
Ivy Cottage is a quaint and comfortable private cottage tucked away on a quiet street in the heart of Old Town. With a cozy queen bedroom, fully equipped kitchen, inviting living space, private front and back porches, and a heated swimming pool just steps from the back porch, it offers an easy and relaxed way to experience Key West.
Spend the morning with coffee on your private porch. Walk to the beach, explore Duval Street, browse local shops and galleries, then come home and cool off in the pool.
With one convenient parking space included, Ivy Cottage gives you the charm of a historic Old Town stay with the everyday comforts that make a longer visit feel like home.


-Drew, July 2026
Quiet enough to relax. Close enough to walk everywhere.
Ivy Cottage sits on a quiet street in the heart of Old Town, close to restaurants, beaches, shopping and attractions. Leave your car in the private parking space and explore Key West on foot or by bicycle.
Duval Street
10 minute walk
Local Dining & Shopping
5-20 minute walk
Higgs Beach
14 minute walk
Live Music & Nightlife
10 minute walk
Southernmost Point
16 minute walk
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The entire cottage is yours during your stay. Start the morning in the kitchen, relax in the living area or step outside onto one of your private porches with a cup of coffee. With a full kitchen, laundry, comfortable living space, fast WiFi and private outdoor areas, Ivy Cottage makes it easy to settle into the rhythm of Key West rather than simply passing through.

The heated swimming pool is shared with three other cottages on the property and sits just steps from Ivy Cottage's back porch. Spend an afternoon cooling off between adventures, stretch out on the loungers or take a refreshing swim before heading out for dinner.

Leave the car in your dedicated parking space and explore the island on foot or by bicycle. Restaurants, shopping, beaches and attractions are all within easy reach, making Ivy Cottage an ideal home base for enjoying Key West at your own pace.
Ivy Cottage combines the charm of a private Old Town cottage with the everyday comforts that make a Key West stay simple.
One dog is welcome with advance approval.
A $200 pet fee applies and the dog must weigh 50 pounds or less. Dogs must be crated when left alone and may not bark or disturb neighbors. Guests are responsible for cleaning up after their pets both inside and outside the home.
Because Ivy Cottage has wood floors, guests traveling with pets should place a tray beneath food and water bowls to prevent moisture damage. Dogs should arrive with nails trimmed and filed to help prevent scratches.
Please contact us before booking if you plan to bring your dog.
There is something wonderfully appealing about having your own little cottage in Key West. Ivy Cottage offers a cozy and comfortable home base in the heart of Old Town, with private indoor and outdoor spaces, a heated pool just steps from the back porch, and the freedom to experience the island at your own pace.
Mornings begin gently here. Brew coffee in the fully equipped kitchen, open the door to the porch, and enjoy the quiet before the day begins. With a comfortable queen bedroom, an inviting living area, and a dedicated dining space, Ivy Cottage has everything you need for a relaxed start to the day.
From there, set out and explore. Old Town Key West is remarkably walkable, and Ivy Cottage places you close to the restaurants, beaches, galleries, shops, and attractions that draw visitors to the island. Walk to Duval Street for breakfast or lunch, spend the afternoon at the beach, or wander through the historic streets and colorful architecture of Old Town.
When you return, there is no need to go anywhere else. The heated swimming pool is just steps from the back porch, making it easy to cool off after a day in the Florida sun. Stretch out on a pool lounger, take a refreshing swim, or simply relax outdoors and enjoy the tropical surroundings.
For travelers searching for a Key West vacation rental with a pool, Ivy Cottage offers an especially appealing combination: a private, charming cottage with a heated swimming pool practically outside the back door.
The pool is shared with three other cottages on the property, creating a relaxed and welcoming atmosphere while still allowing you to enjoy the privacy of your own home. After a morning exploring Old Town, return for a swim, unwind on the loungers, and spend the afternoon embracing the slower pace of island life.
The private front and back porches provide even more space to enjoy the outdoors. Dine al fresco, settle into a comfortable chair with a book, or spend a quiet evening at home after dinner.
Ivy Cottage is situated in the heart of Old Town, on a quiet street that feels removed from the busiest parts of the island while keeping you close to everything.
Duval Street, restaurants, shops, beaches, and historic attractions are all within easy reach. The Tennessee Williams Museum, Conch Train Tour, and Harvey Rest Beach Park are approximately a 10-minute walk away, making it easy to explore without getting behind the wheel.
And when you do want to venture farther afield, your dedicated parking space is waiting for you.
Ivy Cottage is more than a place to spend a few nights. With a full kitchen, private laundry, comfortable living space, fast WiFi, and inviting outdoor areas, it is especially well suited to extended stays.
Settle into the neighborhood, find a favorite coffee shop, walk to the beach in the morning, spend an afternoon by the pool, and prepare dinner at home to enjoy on the porch. Rather than simply visiting Key West, you can settle into its rhythm and experience the island as a local might.
That is the charm of Ivy Cottage: a little cottage in a wonderful location, offering an easy and memorable way to experience Key West.
Book direct for the best rates.