Walk Downtown & Waterfront | Dunedin's Best Street

This light-filled two-bedroom cottage gives up to four guests the privacy and comfort of a full home while placing you close enough to leave the car behind and experience Dunedin on foot. Honeymoon Island, Caladesi Island, Clearwater Beach, and the Dunedin Causeway are also within an easy drive.

What guests love
• Beautiful residential setting on one of Dunedin’s most prized streets
• One block from downtown Dunedin
• Easy walk to the waterfront, marina, Pinellas Trail, and TD Ballpark
• King bedroom plus a second bedroom with two twin beds
• Full kitchen, comfortable living room, and in-home laundry
• Private fenced front yard and private rear courtyard — great for children and pets
• Grill and fire pit
• Free on-site parking
• Pet-friendly accommodations

Picture yourself here
Begin the morning with coffee in your private courtyard or relax in the fenced front yard as the neighborhood comes to life. From the cottage, stroll into downtown for breakfast, browse the boutiques along Main Street, explore the Pinellas Trail, or walk to the marina and waterfront in less than five minutes.
Spend the afternoon at Honeymoon Island, attend a Blue Jays spring-training game, or enjoy one of Dunedin’s many festivals. In the evening, walk to dinner, local breweries, and live music without worrying about downtown parking—then return to the comfort of your own private space.

About Pickets Cottage
Pickets Cottage is a two-bedroom, one-bath cottage with approximately 1,100 square feet of comfortable living space. Its light and airy coastal-farmhouse style creates a relaxed home base for couples, friends, or a small family visiting Dunedin.

The primary bedroom features a king bed, while the second bedroom offers two twin beds. The cottage also includes a full kitchen, dining area, comfortable living room, and in-home laundry.

Outside, guests have exclusive use of the fenced front yard and rear courtyard, along with a grill and fire pit.

Pickets is the front cottage on a property with two separate vacation homes. Palms Cottage, a two-bedroom, two-bath rental, is located farther back on the property. Each cottage has its own private entrance, interior living space, yard, and outdoor amenities. The driveway and parking area are shared, and guests may occasionally see those staying at the neighboring cottage when arriving or departing.

Traveling with a larger group? Pickets Cottage and Palms Cottage may be booked together, subject to availability, giving family and friends the convenience of staying close while enjoying two separate private homes.

The location
From the cottage, you can easily walk to:
• Main Street restaurants, breweries, and boutiques
• Dunedin Marina and the waterfront
• The Pinellas Trail
• Downtown festivals and community events
• TD Ballpark and spring-training games

Good to know
• The cottage accommodates up to four guests with one king bed and two twin beds.
• The home has one shared bathroom.
• Palms Cottage is a separate vacation rental located farther back on the same property.
• The front yard, courtyard, grill, and fire pit are private to Pickets Cottage.
• The driveway and parking area are shared with Palms Cottage.
• Pets are welcome subject to the property’s pet rules and applicable pet fee.

What guests are saying
“Right in the middle of it all, yet tucked away on a quiet street.”
“Beautiful home in a beautiful spot, easily walkable to Main Street.”
“Short walk to downtown, but off the beaten path enough to feel quiet and peaceful.”
“The neighborhood is super cute and charming.”
“The home was very clean, well appointed, and filled with thoughtful extras.”


Guests have private access to the entire Pickets Cottage, including the fenced front yard, rear courtyard, grill, and fire pit. Palms Cottage is a separate rental located farther back on the property; the two cottages do not share interior spaces or private outdoor areas. The driveway and parking area are shared. A unique door code will be provided a few days before arrival for easy self check-in.

We’re readily available if you need assistance before or during your stay. We’re happy to help with questions, local recommendations, or anything that may make your visit more comfortable, while also respecting your privacy and giving you space to enjoy the cottage.

We are located on one of Dunedin's prettiest and centrally located streets. Enjoy the highlights of the town all within easy walking distance, including:-

- Downtown with its many restaurants, cafes, bars, breweries and boutiques to explore, as well as a weekly Green market and many festivals throughout the year.
- Dunedin Marina & Waterfront - enjoy spectacular sunsets and stunning water views from popular spot
- Pinellas Walking Trail - a 40 mile trail starting in St Petersburg and ending in Tarpon Springs, taking in Dunedin & Clearwater along the way.
- Rent bikes at Kafe Racer (4 blocks away) to explore the whole town on wheels
- Edgewater Park - Views of Clearwater Beach across St Joseph's Sound
- Nature's Patch - Local organic grocery store only 5 minutes walk

Our location doesn't get much better for enjoying all the delights of Dunedin - voted one of America's best walkable towns!

Pet policy: Dogs may be accepted with prior approval, and applicable pet fees apply. Cats are not permitted. Please include the number, size, and breed of each dog when submitting your reservation request.

Interior steps: The cottage has two single interior steps: one between the dining and living areas and one between the kitchen and primary bedroom. Guests with mobility concerns should consider whether this layout will be suitable for their stay.

Two-cottage property: Palms Cottage is a separate vacation rental located farther back on the property. Each cottage has its own private home and outdoor areas. Only the driveway and parking area are shared.

Exterior security cameras: Exterior security cameras are present for property security. Cameras monitor the front entrance, driveway and shared parking area, as well as the exterior rear entrance. They do not monitor the interior of either cottage. No cameras are located inside the home.