Southern Pines holiday rentals

We found 624 holiday rentals — enter your dates for availability
Discover a selection of 88 homes, 20 apartments and other holiday rentals in Southern Pines that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Southern Pines

Showing deals for:1 Jan - 8 Jan

Kitchen 2
Front
Dining
Walk to the Village Center
Exceptional
(79 reviews)

The Craddock - Tufts Home & Antique Carriage House - 6BR 5.5 Baths - Sleeps 12+

Pinehurst

11% off
AU$12,707
for 7 nights, 1 cottage
AU$1,815 per night
includes taxes & fees
The Craddock - Tufts Home & Antique Carriage House - 6BR 5.5 Baths - Sleeps 12+
Dining Room and Kitchen from Living Room
Front Elevation
Private Outdoor Patio and Seating Area
Kitchen
Exceptional
(68 reviews)

Scituate House Walk to the US Open - Old Town Charm 6BR - 6.5 Baths - Sleeps 12+

Pinehurst

11% off
AU$12,707
for 7 nights, 1 cottage
AU$1,815 per night
includes taxes & fees
Scituate House Walk to the US Open - Old Town Charm 6BR - 6.5 Baths - Sleeps 12+
Interior
Exterior
Private kitchen
Interior
Exceptional
(178 reviews)

Pinehurst Vacation House w/ pool & 9 beds

Pinehurst

8% off
AU$6,283
for 7 nights, 1 home
AU$898 per night
includes taxes & fees
Pinehurst Vacation House w/ pool & 9 beds
Outdoor dining
Private kitchen
Dining
Interior
Exceptional
(6 reviews)

Banjos Golf Retreat- In the heart of Pinehurst

Pinehurst

7% off
AU$8,133
for 7 nights, 1 home
AU$1,162 per night
includes taxes & fees
Banjos Golf Retreat- In the heart of Pinehurst
Interior
Private kitchen
Room
Exterior
Exceptional
(112 reviews)

Large House w/ Private pool - perfect for Golfing Groups 12 beds in 6 bedrooms

Pinehurst

8% off
AU$10,627
for 7 nights, 1 home
AU$1,518 per night
includes taxes & fees
Large House w/ Private pool - perfect for Golfing Groups 12 beds in 6 bedrooms
Enjoy some peace and tranquility after chasing the balata!
Kitchen with new granite, new floors, new backsplash, new cooktop and vent
Foyer Entry
Property grounds
Exceptional
(88 reviews)

A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!

Pinehurst

8% off
AU$5,664
for 7 nights, 1 home
AU$809 per night
includes taxes & fees
A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!
Living Room
Outdoor dining
Kitchen
Front View
Exceptional
(44 reviews)

3,100+ Sq. Ft, 12 Beds, Foosball, Ping Pong and Shuffleboard, Patio and Grill

Pinehurst

8% off
AU$7,492
for 7 nights, 1 home
AU$1,070 per night
includes taxes & fees
3,100+ Sq. Ft, 12 Beds, Foosball, Ping Pong and Shuffleboard, Patio and Grill
Dining
Terrace/patio
Private kitchen
Living area
Exceptional
(39 reviews)

4 Bedroom 4.5 Baths, Sleeps 8 on course #5

Pinehurst

7% off
AU$3,724
for 7 nights, 1 home
AU$532 per night
includes taxes & fees
4 Bedroom 4.5 Baths, Sleeps 8 on course #5
Living area
Terrace/patio
Interior
Dining
Exceptional
(38 reviews)

Three levels 3400 Sq. Ft., New Bathrooms, 4 BR, 4 BA, Pool Table

Pinehurst

8% off
AU$5,052
for 7 nights, 1 home
AU$722 per night
includes taxes & fees
Three levels 3400 Sq. Ft., New Bathrooms, 4 BR, 4 BA, Pool Table
Room
Dining
Exterior
Living area
Exceptional
(19 reviews)

Spacious 4 BD Golf Getaway with Game Room!

Aberdeen

7% off
AU$3,479
for 7 nights, 1 home
AU$497 per night
includes taxes & fees
Spacious 4 BD Golf Getaway with Game Room!
Exterior
Dining
Dining
Private kitchen
Excellent
(18 reviews)

Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

Pinehurst

7% off
AU$1,706
for 7 nights, 1 home
AU$244 per night
includes taxes & fees
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Cook your favorite meal in our spacious kitchen, complete with gas stove!
Kitchen overlooking main living room
Welcome to your home away from home in Southern Pines!
1st floor
Exceptional
(9 reviews)

19th Hole - Pickelball, Park, Walk to Downtown

Southern Pines

7% off
AU$3,999
for 7 nights, 1 home
AU$571 per night
includes taxes & fees
19th Hole - Pickelball, Park, Walk to Downtown
Dining
Living area
Interior
Private kitchen
Wonderful
(18 reviews)

Beautiful 1 Bed Condo on Pinehurst Course No.5!

Pinehurst

7% off
AU$1,694
for 7 nights, 1 home
AU$242 per night
includes taxes & fees
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Living area
Private kitchen
Room
Living area
Exceptional
(9 reviews)

Private Home in Pinehurst - Super close to the resort and The Village

Pinehurst

6% off
AU$3,795
for 7 nights, 1 home
AU$542 per night
includes taxes & fees
Private Home in Pinehurst - Super close to the resort and The Village
Weymouth House
Golf
Exterior detail
Screen porch and balcony
Exceptional
(20 reviews)

The Maine House - Downtown Southern Pines

Southern Pines

7% off
AU$2,724
for 7 nights, 1 home
AU$389 per night
includes taxes & fees
The Maine House - Downtown Southern Pines
View from the kitchen out toward Pinehurst's Course #5
Beautiful appointed and comfortable living area
Dining area, attached to living room.
Spacious and comfortable living area
Exceptional
(23 reviews)

Pinehurst 2-bedroom, 2-bath Condo Available for Rent

Pinehurst

7% off
AU$2,175
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
Pinehurst 2-bedroom, 2-bath Condo Available for Rent
Living area
Living area
Room
Dining
Exceptional
(12 reviews)

Pinehurst Retreat - Near No. 2

Pinehurst

7% off
AU$2,642
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
Pinehurst Retreat - Near No. 2
Living area
Interior
Living area
Interior
Exceptional
(6 reviews)

Newly Renovated Golf Front Pinehurst #5 Condo

Pinehurst

7% off
AU$2,235
for 7 nights, 1 apartment
AU$319 per night
includes taxes & fees
Newly Renovated Golf Front Pinehurst #5 Condo
View from entry
View from kitchen to Living area and porch
Kitchen view from dining room
Porch w/4 rocking chairs, side tables, mini fridge
Exceptional
(32 reviews)

Premier condo nestled on #3. 12-minute walk to Pinehurst Village. All new!

Pinehurst

7% off
AU$2,041
for 7 nights, 1 apartment
AU$292 per night
includes taxes & fees
Premier condo nestled on #3. 12-minute walk to Pinehurst Village. All new!
Private kitchen
Living area
Golf
Room
Exceptional
(103 reviews)

Newly Renovated – 2BR, 2BA, Pinehurst #3 and #5, a skip and a hop to Clubhouse

Pinehurst

7% off
AU$1,989
for 7 nights, 1 apartment
AU$284 per night
includes taxes & fees
Newly Renovated – 2BR, 2BA, Pinehurst #3 and #5, a skip and a hop to Clubhouse

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Captivating Southern Pines will entice you

The area's entertainment and opera are just some of the reasons to come on holiday to Southern Pines. This city's golfing, local tours and shopping draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Southern Pines

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and check out everything that makes Southern Pines a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mid Pines Golf Club (1.4 mi / 2.2 km)
  • Pine Needles Golf Club (1.4 mi / 2.2 km)
  • Talamore Golf Resort (2.4 mi / 3.9 km)
  • Pinehurst No. 9 (3 mi / 4.8 km)
  • Pinehurst Resort (4.4 mi / 7.2 km)
  • Foxfire Golf and Country Club (10.4 mi / 16.7 km)

Exploring the natural features in Southern Pines

Whether you're an outdoor enthusiast or just want to take in the scenery, Southern Pines is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Pinehurst Lake (5.7 mi / 9.2 km)
  • Reservoir Park (2.9 mi / 4.6 km)
  • Sandhills Horticultural Gardens (3.6 mi / 5.8 km)
  • Hillcrest Park (9 mi / 14.5 km)
  • Lake Luke Marion (11.2 mi / 18 km)
  • Nancy Kyser Park (11.6 mi / 18.7 km)

Transport to and around Southern Pines

Fly into Fayetteville, NC (FAY-Fayetteville Regional), the closest airport, located 31.2 mi (50.1 km) from the city centre.

If you prefer train travel, you can make your way to Southern Pines Station.

Frequently asked questions

What is the best area to stay in Southern Pines when booking a holiday rental?
When considering a holiday rental in Southern Pines, North Carolina, the downtown area is an excellent choice. This vibrant neighbourhood is known for its charming shops, delightful cafés, and a warm community atmosphere. Staying here places you within easy reach of several top attractions, including the stunning Pinehurst Resort, renowned for its golf courses and beautiful grounds. The nearby Weymouth Centre for the Arts and Humanities is also a must-visit, offering a glimpse into the local arts scene and hosting various events throughout the year.In terms of properties, the downtown area features a range of options, from quaint cottages to larger family homes, suiting different group sizes and preferences. Additionally, the picturesque parks in the area provide lovely spots for relaxation and leisurely strolls, making it an ideal base for exploring all that Southern Pines has to offer.
What is the most popular type of holiday rental accomodation in Southern Pines?
In Southern Pines, holiday houses are the most popular type of holiday rental, with around 276 available throughout the area. These properties provide ample space, featuring multiple bedrooms, fully equipped kitchens, and often private outdoor areas for relaxation. Many are situated in peaceful neighbourhoods, making them ideal for families or groups seeking a tranquil escape while exploring the charming town and nearby Pinehurst. Additionally, there are approximately 60 villas, 48 apartments, and 40 cottages, each offering their own unique amenities, such as communal pools or gardens, suiting various traveller preferences.
Are there any family house rentals in Southern Pines?
In Southern Pines, North Carolina, there is a wide selection of family-friendly houses available—around 58 options for those seeking a memorable getaway. The area is known for its charming, tree-lined streets and close proximity to several parks and recreational activities, making it an ideal spot for families.Many of the properties in Southern Pines feature spacious living areas, fully equipped kitchens, and outdoor spaces for children to enjoy. Some homes come with amenities such as private gardens, patios for barbecues, and even game rooms, ensuring that both adults and kids have plenty of entertainment options.Visitors can take advantage of nearby points of interest, including the scenic Pinehurst Resort, which offers golf courses and dining experiences, as well as the lovely Weymouth Woods-Sandhills Nature Preserve, superb for hiking and exploring nature.
Can I rent a holiday home with a pool or hot tub in Southern Pines?
In Southern Pines, there are several holiday homes available for rent with pools and hot tubs, with approximately 16 options to choose from. This charming town, known for its golf courses and picturesque landscapes, offers a range of properties that cater to those seeking relaxation and leisure. Many of these rentals feature private pools, hot tubs, spacious outdoor areas, and well-equipped kitchens, making them great for families or groups looking to unwind after a day of exploring the local area.Travellers can expect amenities such as Wi-Fi, air conditioning, and comfortable living spaces, ensuring a pleasant stay. Additionally, Southern Pines is close to various attractions, including golf courses and parks, providing opportunities for outdoor activities.
Are there pet-friendly house rentals in Southern Pines?
In Southern Pines, there are numerous pet-friendly house rentals available, with about 55 options to choose from. Many of these properties come equipped with amenities such as spacious backyards, pet-friendly furnishings, and sometimes even features like dog runs or pet washing stations, making them ideal for travellers with furry companions.The area is known for its charming southern atmosphere and proximity to several parks, including the scenic Southern Pines Park, which offers walking trails and open spaces great for pets. Additionally, the nearby Weymouth Woods-Sandhills Nature Preserve provides expansive natural areas where pets can enjoy outdoor activities alongside their owners.
Are there any remote work holiday rentals in Southern Pines?
In Southern Pines, there is a substantial selection of remote work holiday rentals available, with around 384 options to choose from. This charming town in North Carolina offers a tranquil environment ideal for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated workspaces, and even computer monitors in some units, ensuring a productive atmosphere.The neighbourhoods around Southern Pines provide a delightful blend of Southern hospitality and natural beauty. Visitors can enjoy proximity to various local parks and golf courses, superb for unwinding after a day of work. The area also features quaint shops and restaurants, adding to the overall appeal for both remote workers and their families. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Southern Pines?
In Southern Pines, popular holiday rental amenities typically include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also feature coffee and tea makers, enhancing the comfort of morning routines. Onsite parking is commonly available, making it easy for visitors to explore the area without worrying about street parking. Additionally, most properties come with decks or patios, providing outdoor spaces for relaxation or socialising while enjoying the pleasant North Carolina climate.
What are the top attractions in Southern Pines?
In Southern Pines, visitors can enjoy a charming blend of outdoor activities and cultural attractions. The historic downtown area is a delightful spot to explore, featuring quaint shops, local art galleries, and inviting cafes superb for a leisurely afternoon.For golf enthusiasts, the area is renowned for its exceptional golf courses, with several public and private options available, including the famous Pinehurst Resort located nearby. This resort offers a rich golfing history and beautifully landscaped grounds.Nature lovers can take advantage of the nearby Weymouth Woods-Sandhills Nature Preserve, where hiking trails wind through longleaf pine forests, providing opportunities for birdwatching and enjoying the serene environment. Additionally, the Sandhills Community College offers various cultural events and performances throughout the year, making it a vibrant part of the local scene.
Are all fees included in the Southern Pines holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Southern Pines holiday homes with parking?
Stayz offers a wide selection of holiday homes in Southern Pines with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Southern Pines holiday homes?
You can find great discounts on holiday homes in Southern Pines on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Southern Pines holiday home booking on Stayz?
To find Southern Pines holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Southern Pines?
A long-stay holiday home in Southern Pines is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Southern Pines holiday home?
Book your Southern Pines holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Southern Pines?
Prices for holiday homes in Southern Pines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Southern Pines to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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