Hi, we’re Damara and Birche, the team behind Stay Well Vacation Rentals. From chic retreats to cozy cabins, we offer the perfect getaway. Birche’s background in Special Ops Aviation and Damara’s passion for exceptional guest experiences ensure every stay is unforgettable. We've built a diverse portfolio across commercial, multi-family, and short-term rentals, focusing on comfort and seamless stays. We look forward to hosting you!

Nestled at the back of the main residence, Sienna Cottage is the perfect home away from home for your next trip to Southern Pines. Fully equipped kitchen, spacious living room and table for four, this property can sleep up to four guests. Enjoy easy access from the blue stone gravel drive, as well as dedicated parking for Airbnb guests conveniently located behind the main home - with plenty of auxiliary parking if you have more than one vehicle, and street parking available in case you need it. Sienna at 255, is the perfect retreat for couples or traveling professionals looking to be in a lively and walkable area. When we say walking distance from downtown, we mean it! Below are a few of our favorite local spots worth checking out. Plan ahead and book the entire Shire retreat, made up of three luxury spaces, this property can sleep up to 10 guests. Add privacy and comfort to any family vacation or work trip. - 400' to The Jefferson Inn (live music on the weekends) - 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) - 0.2 miles to Ashtens - 0.2 miles to The Bell Tree Tavern - 0.3 miles to Southern Pines Growler - 0.3 miles to So Pines Pizza - 0.4 miles to Southern Prime Steakhouse (fancy dinner) - 0.6 miles to Betsy's Crepes (the best breakfast spot around, in our humble opinion) - 0.9 miles to Sly Fox (the butter chicken dish is to die for - don't take my word for it) - The list goes on and on... EV Charging is available just a short walk (0.2 miles) from the property at the Southern Pines Library.

Located just one block from the heart of downtown Southern Pines, this charming home offers the perfect blend of convenience and comfort. Step outside and find yourself within walking distance of a variety of local attractions, including trendy restaurants, craft breweries, a cozy wine shop, vibrant coffee spots, and unique boutiques. Whether you're looking to enjoy a leisurely meal, explore local shops, or unwind with a drink, everything you need is just moments away from your doorstep. Experience the best of Southern Pines with this prime location!