
Vacation rentals in Southern Pines
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Top-rated vacation rentals in Southern Pines
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The Ace Cottage - Tiny-home Feel, Close to golf
Unwind in the privacy of this adorable tiny-home! Just over a mile from downtown Southern Pines and less than 15 min to the famous Pinehurst Resort. Features a King size Nectar bed, Fire TV, WiFi, shower with tankless water heater a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge w/ freezer, toaster oven, and electric skillet), beautiful stone patio, professional landscaping, pet yard access, brand new floors, and a large driveway. The perfect spot for a quiet night!

Charming 1 bedroom guesthouse on 4 acres, hot tub
Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee for dogs. sorry, no cats.

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.

Finally Home Farm Bed and Barn
Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

Lakeside Cottage nestled near Pinehurst and CHP
Bellago Farm Cottage is nestled in the woods off the edge of the North Carolina Game Lands. It is 6 miles from the Carolina Hotel/Pinehurst Resort and the famous Pinehurst #2 Golf Course, and 8 miles from the Carolina Horse Park. The lakeside cottage welcomes you to fishing and swimming its spring-fed 9-acre, very clear waters. Enjoy relaxing between activities with easy access wi-fi or tv. If you are traveling to the area for equine competition, horse boarding is available.

Historic Southern Pines Carriage House
Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

The Knotty But Nice Treehouse of Pinehurst
Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

Golf Resort, Private Entrance, Bath & Kitchenette
This Condo is located on Talamore Golf Resort and is minutes away from many world class golf courses, to include Pinehurst Resort. Approximately 40 minutes to Fort Bragg for Military/DOD civilians who are TDY or house hunting; 4 miles to First Health Moore Regional Hospital for travel nurses; 2.5 miles to Sandhill community college; Reservoir Park is a 250 yard walk from the front door and includes a 95 acre lake, and more than 12 miles of Greenway Trails.

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!

Tanglewood Farm B&B Horse Farm- The Fox Den Suite
Welcome to the Fox Den Suite at Tanglewood Farm! The Fox Den is a private one bedroom (KING) , one bathroom beautifully decorated apartment on our beautiful 10 acre horse farm. Nestled in the heart of North Carolina's beautiful horse county, just minutes from charming downtown Southern Pines. Enjoy local breweries, shops, amazing restaurants and over 100 beautiful golf courses. Weekend Breakfast for Two Sat and Sun Avail for Purchase at $30/morning

Delightful Bungalow in Historic Downtown
LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming, quaint & cozy 1930's bungalow. Just steps from our idyllic downtown of Southern Pines. (Literally 1 block!) You will be treated to a private, clean, cozy and updated space filled with everything you will need for a wonderful stay. 1 bedroom / 1 bath / 1 sleeper sofa. Street parking. Strict 'No Pet' policy.

Peaceful Horse Farm Retreat
Perfect for a getaway! Anahata Farm Retreat is nestled in the midst of Southern Pines' horse country, one hour south of Raleigh. We are located near the end of a quiet, private dirt road. There is space to roam and animals to greet. This a peaceful, pet-friendly spot, guaranteed to help you relax and reconnect. For more pics, search socials for @anahatafarm. Please do not book this room unless you will be the one staying here. NO SMOKING.
Popular amenities for Southern Pines vacation rentals
Other great vacation rentals in Southern Pines

The Kensington Cottage

Pinehurst #6 Garden Getaway

Belleview on Bennett, Heart of Downtown So Pines!

Crosswind Farm

The Gallery - 2 bd Boutique Southern Pines Cottage

The Cottage on Midland

Charming Cottage in Downtown Southern Pines

Private&Comfortable Studio for 2 in Southern Pines
Quick stats about vacation rentals in Southern Pines
Total rentals
370 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
30 properties have a pool
Frequently Asked Questions
Where should I stay in Southern Pines?
Make yourself at home in Southern Pines by choosing from our most frequently booked neighborhoods. We have over 370 vacation rentals in Downtown Southern Pines, over 50 vacation rentals in Highland Trails, and over 240 vacation rentals in Talamore.
Are there pet-friendly vacation rentals in Southern Pines?
Four-legged friends are welcome in Southern Pines. Choose from more than 150 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Southern Pines?
Yes! Work meets play with ease at over 210 vacation rentals in Southern Pines featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Southern Pines vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Southern Pines, available on Airbnb. Make a splash and soak up the sun in style!
Do villa rentals in Southern Pines have wifi?
Absolutely! We offer over 10 villa rentals with wifi in Southern Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southern Pines have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Southern Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southern Pines have a gym?
Absolutely! We offer over 30 house rentals with a gym in Southern Pines. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Southern Pines?
Southern Pines has more than 200 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do townhouse rentals in Southern Pines have air conditioning?
Absolutely! We offer over 30 townhouse rentals with air conditioning in Southern Pines. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Southern Pines?
Experience the best of Southern Pines with our guesthouse rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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