Holiday houses in Southern Pines
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Quick stats about holiday rentals in Southern Pines
Total holiday rentals
Explore 390 holiday rentals in Southern Pines
Nightly prices starting at
Southern Pines holiday rentals start at $68 NZD per night before taxes and fees
Verified guest reviews
Over 17,040 verified reviews to help you choose
Family-friendly holiday rentals
260 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 140 rentals that welcome pets
Holiday rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Wi-Fi availability
380 of Southern Pines holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Southern Pines rentals
4.9 Average rating
Southern Pines stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated holiday rentals in Southern Pines
Guests agree: these stays are highly rated for location, cleanliness and more.
The Bookery - Bright, Airy home with Fenced Yard
Relax in our bright, 2500+ sqft home on nearly 3/4 of an acre with a large fenced back yard. Pet friendly wood floors throughout, and great spaces for quality time. 1 mile to downtown and only 6 miles to Pinehurst Golf Resort and 13 miles to Carolin Horse Park. Enjoy the sunroom, fully stocked kitchen with gas stove and double oven, the gorgeous patio, or the inviting couch to watch a movie with the whole family! Available for short term leases as well. Looking forward to hosting you and yours!
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Luxury Golf Front Condo
Located steps away from the Longleaf Golf Course and the National Headquarters for the U.S. Kids Golf Training Academy, this inviting 2 BR/2BA condo is an ideal getaway home. Includes a spacious living area with full kitchen, dining area, and living room along with private bathrooms in each bedroom. Can comfortably sleep 6 and is perfect for families, golfers, or the traveler looking to relax and unwind in the Sandhills. Centrally located between downtown Southern Pines and Pinehurst Village.
LocationFamilyHospitality
The Ross Retreat - In Pinehurst
Your entire group will enjoy this central location to 40+ golf courses in Moore county with easy access to restaurants and close to grocery stores. This gorgeous home with custom woodwork and backyard oasis is the perfect retreat for families and golfers alike. Enjoy comfortable beds with down pillows and high end mattresses with mattress pads and a fully stocked kitchen in this newly furnished home. If you appreciate the little things like HEPA air filters and quite dishwashers, we got you.
LocationFamilyBarbecue
New 5 Bedroom Cottage on Pine Needles Golf Course!
New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.
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SoPi Oasis | Hot Tub | Fire Pit | Game Room | Pets
Welcome to our amenity packed space with a modern design that welcomes golfers, families, and pets alike! (NO CHORE LIST FOR GUESTS!) Simply check your worries at the door, we will take care of the rest upon checkout! This meticulously designed space promises an unforgettable escape for golf enthusiasts and relaxation seekers alike. Unwind in the game room, relax around the covered fire table, or enjoy the serenity in our peaceful backyard oasis. Located at the center of the US Golf Mecca!
LocationFamilyTV
High End Kitchen, Game Room, Long Term Rental
This Blue Beauty was built in 2025, and offers a great location close to Downtown Southern Pines. Walk to shopping & dining, as well as to pickleball/playground at Memorial Park. This 4 bed/3 bath home offers an open concept main floor, as well as a fitness area and chill zone on the 2nd floor. The garage features a game room - including a pop-a-shot basketball game, shuffleboard, darts & beer pong table. Enjoy the sunset & warm nights on the back deck with a gas grill and cozy couch.
ValueFamilyKitchen
The Pinecone Cottage - a Southern Pines escape
Nestled within the charming town of Southern Pines, this modern cottage offers an escape in the heart of the Sandhills region of North Carolina. Everything is walking distance through towering Carolina pines. The quaint town offers a vintage peacefulness that's hard to find nowadays, while still affording the comforts of modern living. Come experience the historic sandhills region, home to world-class golf, pine trees, and tons of natural beauty. Welcome to the Pinecone Cottage.
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The 19th Stay - Cozy Getaway Near Pinehurst
Welcome to the 19th Stay, your cozy getaway near Pinehurst. Perfect for golf trips, couples or family escapes. Our brand new home features clean and comfy bedrooms, kid friendly bunk beds and all the essentials for a stress free stay. Located in the heart of Southern Pines, you’ll be just minutes from world-class golf, equestrian experiences, gorgeous parks, dining, and downtown shops. Relax, recharge and enjoy a home that’s as central as it is welcoming
LocationFamilyCleanliness
Knollwood Manor - The Historic Mid Pines Mansion
One of-a-kind historical estate overlooking the 15th fairway of the Donald Ross designed Mid Pines Golf Course in Southern Pines. Often described as having one of the ''best'' golf course views in The Sandhills, the elegance of this 5,212 sq ft English Country Manor exists in concert with 2.06 acres of natural beauty. The sweeping back lawn overlooking the golf course is the perfect setting for entertaining or unwinding in the Southern Pines / Pinehurst area.
LocationFamilyHospitality
Cottage on Ridge -Short & Extended Stays
This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. Located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This unit is downstairs with 1 bedroom (Queen) & 1 bath, a full kitchen, a dedicated work space, and shared laundry room in the back of the home. It has a private entrance from the front door. Come stay with us for a short stay or extended stay!
FamilyValueSolo travel
Cozy Cottage - pet friendly, great location!
Enjoy a cozy and premium experience at this centrally-located place. Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines. Tons of amenities including: Fenced in backyard Outdoor patio with fire pit and grill Wood fireplace Smart TV Washer and dryer Desk workspace Fast WiFi Smart Thermostats 2 car driveway Full kitchen …and more!
ValueFamilyCheckout
Charming Cottage in Downtown Southern Pines
Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.
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Popular amenities for Southern Pines holiday rentals
Stay near Southern Pines's top sights
Other great holiday rentals in Southern Pines
The Cowboy! Concierge Services, Downtown & Luxury!
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Paradise on Hole#2
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19th Hole - Pickelball, Park, Walk to Downtown
FamilyValueBathroom
Banjos Golf Retreat- In the heart of Pinehurst!
LocationFamilyGetting around
Luxury Stay by Pinehurst No. 2- Where Legends Play
LocationFamilyKitchen
The Reynolds Villa-Golf/Couples Retreat
LocationFamilyPool
The Warren
FamilyLocationAccuracy
ThePalmer*Private*Pool*HotTub*FirePit*CentralDr
FamilyLocationHospitality
When is the best time to visit Southern Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $248 NZD | $253 NZD | $282 NZD | $307 NZD | $289 NZD | $287 NZD | $299 NZD | $274 NZD | $250 NZD | $262 NZD | $279 NZD | $270 NZD |
| Avg. temp | 5°C | 6°C | 10°C | 15°C | 19°C | 23°C | 25°C | 25°C | 21°C | 15°C | 10°C | 6°C |
Frequently Asked Questions
What are the best places to stay in Southern Pines?
Travelers often look for accommodations in or near the downtown area, where restaurants, galleries, and parks are easily accessible. Stays closer to Weymouth Woods Sandhills Nature Preserve are popular with visitors interested in outdoor activities.
What are the best things to do in Southern Pines with kids?
Families can explore the interactive exhibits at the Southern Pines Public Library, play at Reservoir Park’s playgrounds, or take nature walks in Weymouth Woods Sandhills Nature Preserve. Community events and seasonal farmers markets also create a welcoming atmosphere for children.
What are some of the best things to do in Southern Pines?
Explore Weymouth Woods Sandhills Nature Preserve, stroll through downtown boutiques, or attend an art show at a local gallery. Southern Pines also has golf courses, equestrian events, and cozy spots for coffee or live music.
How is the weather in Southern Pines?
Southern Pines has mild winters around 30–54°F (-1–12°C) and warm, humid summers reaching 86–88°F (30–31°C). Spring and fall are comfortable, with moderate rainfall and pleasant temperatures for outdoor activities.
When is the best time to visit Southern Pines?
Spring and fall are often recommended, with comfortable temperatures around 55–77°F (13–25°C) in May and colorful foliage in October. These seasons usually bring outdoor events and opportunities to explore nature with milder weather.
What are the best places to visit in Southern Pines?
Frequently suggested spots include the shops and eateries of downtown, the walking trails at Weymouth Woods Sandhills Nature Preserve, and the historic Weymouth Center for the Arts & Humanities. The area’s farmers markets and art galleries reflect local flavor.
What are some hiking trails in Southern Pines?
Weymouth Woods Sandhills Nature Preserve has several well-maintained trails winding through longleaf pine forests, with interpretive signage about the local ecosystem. Reservoir Park also features multi-use paths along the water for walking, jogging, or birding.
What are some family activities we can do in Southern Pines?
Explore the interactive Southern Pines Public Library, play together at community parks, or walk scenic trails in natural preserves. Families often enjoy seasonal festivals, local ice cream shops, and hands-on art classes.
What are some of the best day trip ideas from Southern Pines?
Consider a day trip to explore botanical gardens, visit neighboring historic towns with antique shops, or hike trails in nearby state parks. The region also has local wineries and art galleries that create diverse outing options.
Are there any pet friendly accommodations available in Southern Pines?
Southern Pines has a variety of pet-friendly vacation rentals, including homes with fenced yards and options near parks. Many hosts welcome travelers with pets; check individual listings for property-specific policies.
What are some local tips for visiting Southern Pines?
Locals suggest exploring Southern Pines’ walkable downtown, sampling fresh baked goods at early-opening cafes, and bringing comfortable shoes for nature trails. The area also has a relaxed pace, so take time to chat with shop owners or enjoy outdoor seating at restaurants.
What is Southern Pines known for?
Southern Pines is known for its historic downtown, equestrian culture, and scenic longleaf pine landscapes. The town has a reputation as a golf destination, with several renowned courses and a welcoming arts scene.
What are the best hidden gems to explore in Southern Pines?
Explore the quiet gardens and literary history at Weymouth Center for the Arts & Humanities, or discover local art studios tucked among downtown shops. Some visitors also appreciate the preserved longleaf pine trails at lesser-known conservation areas.
What are the best foods to try in Southern Pines?
Southern Pines has Southern specialties like shrimp and grits, locally inspired barbecue, and freshly baked biscuits. You will also find seasonal produce at farmers markets and diverse dishes at family-owned eateries.
What should I bring for a trip to Southern Pines?
Bring comfortable walking shoes for exploring nature trails, breathable clothing for warm days, and a light jacket for cooler evenings. A reusable water bottle and sun protection are helpful for outdoor activities, especially in spring and summer.
What is the nightlife in Southern Pines like?
Nightlife in Southern Pines centers on casual bars, wine lounges, and live music venues around downtown. You will also find late-opening cafés and gathering spaces for relaxed evenings with friends.
What are the most popular events or festivals in Southern Pines?
Southern Pines hosts an annual SpringFest street fair, regularly scheduled equestrian events, and arts festivals in the heart of downtown. Holiday parades and live music concerts in local parks are also frequently suggested.
Are there family friendly vacation rentals in Southern Pines?
Many vacation rentals in Southern Pines are family-friendly, with options like homes featuring multiple bedrooms, backyards, or easy access to parks. Hosts often include amenities such as board games, children’s books, or cribs for added convenience.
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