Where Families and Friends Gather Together

Some trips are about the destination. This one is about who you're with. This 1944 whole house, in a quiet, historic pocket on the edge of downtown Pensacola, has hosted reunions, milestone birthdays, weddings, and grandparents meeting grandkids for the first time, families and friends returning again and again because the space makes room for everyone to gather and everyone to breathe.

You'll find that balance throughout the home. Three bedrooms and two bathrooms give every generation their own corner, while the open living areas, spacious deck, and backyard fire pits pull everyone back together in the evening. The Fun Room, with its retro Atari console, 58" TV, and two full beds, tends to become the kids' or teens' unofficial headquarters. Comfy king beds and 50" smart TVs fill the main bedrooms, and the spa bathroom's Jacuzzi soaking tub and rain shower are consistently one of our guests' favorite parts of the stay.

Step outside to a private hot tub on the deck, two fire pits (one propane, one wood-burning), a gas grill, and an outdoor dining table, plenty of room for a group dinner, a quiet morning coffee, or s'mores after dark. The kitchen is fully stocked with everything you need to cook for a crowd, including a Keurig coffee station, and the washer/dryer comes with starter supplies so you can settle in without a grocery run.

You'll have the whole house to yourselves, no shared spaces, no compromises. This cottage-style home has carried the Simmons family name since 1944. Original hardwood floors, arched doorways, and majestic oaks give it a character no new build can match, fully renovated for modern comfort while keeping the story that makes it feel like more than just a rental.

You're just 1.6 miles from Palafox St and the heart of downtown Pensacola, with new neighborhood shops and lunch spots popping up nearby. Pensacola Beach is about a 15-minute drive (9.6 miles), and you're 2 miles from the civic center and 1.7 miles from Maritime Park.

Free parking for up to 3 vehicles on-site, and boat or RV parking may be available, just ask us ahead of your stay.

As local hosts, we're quick to respond and happy to share our favorite spots for food, sightseeing, and entertainment, check out our in-app guide book for our full list. We do occasional exterior lawn and property maintenance and will always give you a heads-up ahead of time so it doesn't disrupt your stay. Owner storage closet is the only space not included, and check-in is contactless with a smart lock code sent the day before your arrival.

We can't wait to host your house full for your family's next gathering.