What are the top rated Winter Rentals in Southern Pines?

There are a lot of options in Southern Pines. If you plan on staying in the Southern Pines area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Southern Pines: <a href="/property/southern-memories-on-3/HA-321923109" class="class="static-page-link"">Southern Memories on #3</a> <a href="/property/condo-in-the-pines-2br-2ba-sleeps-4-military-discount-available/HA-321230095" class="class="static-page-link"">Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available!</a> <a href="/property/convenient-2-bedroom-2-bath-condo-steps-from-pinehurst-clubhouses/HA-3211369066" class="class="static-page-link"">Convenient 2 bedroom 2 bath condo steps from Pinehurst clubhouses</a> <a href="/property/eagle-s-nest-beautiful-golf-front-home-on-pinehurst-6/HA-3211755906" class="class="static-page-link"">Eagle&#39;s Nest! Beautiful Golf Front Home on Pinehurst #6!</a> <a href="/property/pinehurst-tree-house-renovated-golf-course-front-single-family-home/HA-3211386713" class="class="static-page-link"">Pinehurst Tree House Renovated Golf Course Front Single Family Home 🏡</a> <a href="/property/large-house-w-private-pool-perfect-for-golfing-groups-12-beds/HA-3212271045" class="class="static-page-link"">Large House w/Private pool - perfect for Golfing Groups 12 beds</a> <a href="/property/golf-terrace-1-bedroom-1-bath-condo-steps-from-pinehurst-resort/HA-3212711013" class="class="static-page-link"">Golf Terrace 1 bedroom 1 bath condo steps from Pinehurst Resort</a> <a href="/property/relax-in-the-heart-of-pinehurst-on-5/HA-1217466013" class="class="static-page-link"">Relax In the Heart of Pinehurst on # 5!</a> <a href="/property/newly-renovated-2br-2ba-pinehurst-3-and-5-a-skip-and-a-hop-to-clubhouse/HA-3212682973" class="class="static-page-link"">Newly Renovated – 2BR, 2BA, Pinehurst #3 and #5, a skip and a hop to Clubhouse</a> <a href="/property/one-market-square-comfortable-luxury-condo-in-the-center-of-downtown-pinehurst/HA-3211279599" class="class="static-page-link"">One Market Square - Comfortable Luxury Condo in the Center of Downtown Pinehurst</a>

How much does it cost to rent a place to stay near Southern Pines in the wintertime?

The average cost for winter rentals in Southern Pines is $731 per night. Cataloocheemountaincabin has a wide list of great winter places to stay near Southern Pines that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Do you have any winter rentals in Southern Pines that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Southern Pines to find what works for you.

Are there winter accommodations in Southern Pines that have indoor swimming pools?

As of 2026, the data from Cataloocheemountaincabin shows that there are over 1121 private swimming pools or indoor pools accommodations near Southern Pines along with other great amenities.