King Bedrooms, Two Blocks to Gulf, Shopping, and Dining in Old Naples

Upstairs is one of five art-filled, comfort-prioritized rentals on a beautifully rebuilt Old Naples estate dating back to c.1910 - known as Coquina Cottage Estate. The Upstairs Retreat is located directly above the Main House. The Upstairs private entrance is at the back of the property. They are separate units. Guests have rented both the Main House and the Upstairs Retreat. In this case, we give the guests keys to the passageway door at the entrance to the Upstairs.
The three cottages are visible from the kitchen windows, with the landscaping focused on beauty and Monarch Butterflies.

Up the 11 wooden steps, you walk into the living room, with the kitchen set off to the right. The five kitchen windows, and you may catch the orange and black wings of Monarch Butterflies encircling the estate. This historic property is a designated Butterfly Migration Station, and the surrounding gardens attract butterflies throughout the day.

Located just two blocks from the Gulf of Mexico and the white-sand beaches, this Upstairs Retreat is also within easy walking distance of all the dining, boutiques, and charm found on 5th Avenue South and 3rd Street South. The private staircase leads to a large room with the ceiling beams exposed and two large working airplane ceiling fans.

Inside, guests will find a comfortable seating area, a full kitchen with marble countertops, and a bar-style counter perfect for meals or conversation. The kitchen is equipped with all-new appliances, making cooking simple and enjoyable. The home includes two king bedrooms, each with inviting bedding and art accents, along with a full bathroom with a tub located just off the kitchen.

A stackable washer and dryer, two smart TVs, and beach essentials—including a cooler, umbrella, chairs, and towels—ensure a relaxing stay. A grill is also available for easy outdoor dining.

*****Construction has been ongoing across the street for the past eight seasons. Wondering what helps when living near a construction site? In my experience: noise machines and earplugs. I provide these for guests and have lowered the nightly rate accordingly. Pricing is set using the VRBO Market Price Tool, ensuring the nightly rate fairly reflects both value and conditions.

November 2026 - Construction is focused on the finished work and inside. It is quieter than in past years, but still not calm enough for me to take down the warning.

I rely on my reviews to share updates and provide potential guests with guidance. With five rentals on the property and year-round 80% occupancy, past guests will tell the story.