Southern Pines vacation rentals

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Top-rated vacation rentals in Southern Pines

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Vass

4.95 out of 5 average rating, 128 reviews

Peaceful Horse Farm Retreat

Anahata is a quiet farm retreat dedicated to peace and healing. You’ll stay in our Hunt Box - a spacious studio apartment over the barn with pasture view and fully equipped kitchen. There is space to roam and animals to greet. Please read the full listing prior to booking to ensure that this is the right place for you. For more pics, check out our Insta @anahatafarm. NO third-party bookings - please do not book this room unless you will be the one staying here. NO SMOKING. All are welcome here.

Jul 29 – Aug 5

R2,047 ZAR per night

Guest favorite

Cottage in Southern Pines

4.96 out of 5 average rating, 277 reviews

The Ace Cottage - Tiny-home Feel, Close to golf

Unwind in the privacy of this adorable cottage! 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, bathroom with efficiency shower, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge with 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!

Oct 29 – Nov 5

R1,834 ZAR per night

Guest favorite

Home in Pinehurst

4.98 out of 5 average rating, 658 reviews

The Knotty But Nice Treehouse of Pinehurst

NOW ACCEPTING US OPEN 2024 RESERVATIONS! 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 unique rental 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.

Sep 7 – 14

R3,318 ZAR per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 140 reviews

Restored 1920s 2BR Cottage w/Bikes-DWTN So Pines

Experience downtown Southern Pines in a stylish fully restored early-1900's cottage. This home is conveniently located 4 blocks (4 min walk) from Broad Street, where you will find all the shopping, restaurants, and bars. The cottage is 5 minute drive to several world-class golf courses (Mid-Pines, Mid-South, Longleaf, Pine Needles, Pinehurst No. 9, Talamore) just to name a few... and only 10 mins away from the Village of Pinehurst and Pinehurst No.2. Cruise like a local on the free bikes!

Dec 20 – 27

R2,885 ZAR per night

Guest favorite

Farm stay in Southern Pines

4.98 out of 5 average rating, 124 reviews

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.

Dec 2 – 9

R2,565 ZAR per night

Guest favorite

Condo in Southern Pines

4.92 out of 5 average rating, 157 reviews

Relaxing in the Pines

Located 5 min from downtown Southern Pines (Broad St). A great place to stay for golfers, horse lovers, and others visiting to explore Pinehurst, Southern Pines and other surrounding areas. The large screened in porch off of the living room and dinning room which provides peaceful beauty and elegance. Two bedrooms and two full baths, this condo provides you with a wonderful opportunity for anyone wanting to relax and especially for golfers, horse lovers and others..5 PM Check in

Jan 23 – 30

R1,754 ZAR per night

Guest favorite

Guesthouse in Carthage

4.99 out of 5 average rating, 152 reviews

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 and friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, one queen bed and small fold out sofa. 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.

Mar 1 – 8

R2,700 ZAR per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 145 reviews

Loft Cottage on Ridge ? Short & Extended Stays?

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Jan 6 – 13

R2,198 ZAR per night

Guest favorite

Cottage in Pinebluff

4.93 out of 5 average rating, 164 reviews

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.

Aug 5 – 12

R2,448 ZAR per night

Guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 171 reviews

Charming, newly updated Downtown Cottage

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 updated 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your newly landscaped patio, walk around and take in the beautiful sights of this charming Southern town.

Sep 14 – 21

R3,019 ZAR per night

Guest favorite

Guest suite in Southern Pines

4.95 out of 5 average rating, 221 reviews

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.

May 9 – 16

R1,213 ZAR per night

Guest favorite

Condo in Pinehurst

4.99 out of 5 average rating, 102 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

Dec 11 – 18

R2,196 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southern Pines vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Southern Pines's top sights

Walmart Supercenter11 locals recommend

Weymouth Woods - Sandhills Nature Preserve43 locals recommend

Longleaf Golf & Family Club7 locals recommend

Texas Roadhouse4 locals recommend

Chick-fil-A6 locals recommend

LongHorn Steakhouse3 locals recommend

Other great vacation rentals in Southern Pines

Guest favorite

Guesthouse in Southern Pines

4.86 out of 5 average rating, 104 reviews

Solitude at The Shire 255 D - Unit D - Downtown!

Aug 17 – 24

R2,649 ZAR per night

Guest favorite

Condo in Pinehurst

4.94 out of 5 average rating, 149 reviews

Pinehurst Green - 2BD 2BA Golf Front Condo

Sep 5 – 12

R2,546 ZAR per night

Guest favorite

Apartment in Pinehurst

4.98 out of 5 average rating, 215 reviews

Pinehurst #6 Garden Getaway

Feb 11 – 18

R1,474 ZAR per night

Guest favorite

Condo in Pinehurst

4.91 out of 5 average rating, 150 reviews

Right next to the Cradle and the Fair Barn-Perfect

Oct 22 – 29

R2,795 ZAR per night

Guest favorite

Apartment in Southern Pines

4.97 out of 5 average rating, 176 reviews

Tanglewood Farm B&B Horse Farm- The Fox Den Suite

Dec 14 – 21

R2,842 ZAR per night

Guest favorite

Condo in Pinehurst

4.94 out of 5 average rating, 191 reviews

Pinehurst Golf-Front, A+ Location, Clean + Comfy

Jun 21 – 28

R2,190 ZAR per night

Guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 117 reviews

Premier Southern Pines Golf Oasis, Hot Tub Retreat

Jun 20 – 27

R4,619 ZAR per night

Guest favorite

Cottage in Pinehurst

4.93 out of 5 average rating, 242 reviews

Water Oaks Cottage - Near Pinehurst Country Club

Oct 2 – 9

R2,920 ZAR per night

Show all

Other great vacation rentals in Southern Pines

Guest favorite

Guesthouse in Southern Pines

5.0 out of 5 average rating, 14 reviews

Charming Getaway Carriage House with pool

Sep 1 – 8

R1,968 ZAR per night

Guest favorite

Loft in Southern Pines

4.97 out of 5 average rating, 58 reviews

The Caddie’s Cottage, a cozy golf retreat.

Nov 24 – Dec 1

R1,843 ZAR per night

Guest favorite

Bungalow in Southern Pines

4.95 out of 5 average rating, 91 reviews

Crosswind Farm

May 17 – 24

R2,253 ZAR per night

Guest favorite

Vacation home in Southern Pines

5.0 out of 5 average rating, 11 reviews

Horse and Golf Heaven - 2 BR Apt on Horse Farm

Oct 25 – Nov 1

R2,588 ZAR per night

Guest favorite

Condo in Southern Pines

5.0 out of 5 average rating, 30 reviews

Spacious 1 BR condominium right on the golf course

Sep 1 – 8

R2,533 ZAR per night

Guest favorite

Apartment in Southern Pines

5.0 out of 5 average rating, 20 reviews

Private&Comfortable Studio for 2 in Southern Pines

Jul 16 – 23

R2,881 ZAR per night

Guest favorite

Guesthouse in Southern Pines

5.0 out of 5 average rating, 59 reviews

The Kensington Cottage

Jun 19 – 26

R2,178 ZAR per night

Guest favorite

Place to stay in Vass

4.97 out of 5 average rating, 60 reviews

Cozy Cottage On The Water

Sep 12 – 19

R2,708 ZAR per night

Show all

Quick stats about vacation rentals in Southern Pines

Total rentals
440 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
160 properties allow pets
Family-friendly rentals
320 properties are a good fit for families
Total number of reviews
11K reviews
Nightly prices starting at
R384 ZAR before taxes and fees

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 360 vacation rentals in Downtown Southern Pines, over 310 vacation rentals in Talamore, and over 70 vacation rentals in Highland Trails.
Are there pet-friendly vacation rentals in Southern Pines?
Four-legged friends are welcome in Southern Pines. Choose from more than 160 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 240 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 50 vacation homes with pools in Southern Pines, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Southern Pines have wifi?
Absolutely! We offer over 10 condo 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 70 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 50 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 270 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 20 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 townhouse rentals in Southern Pines?
Experience the best of Southern Pines with our townhouse rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Southern Pines vacation rentals

Top-rated vacation rentals in Southern Pines

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Southern Pines vacation rentals

Stay near Southern Pines's top sights

Other great vacation rentals in Southern Pines

Guesthouse in Southern Pines

Condo in Pinehurst

Apartment in Pinehurst

Condo in Pinehurst

Apartment in Southern Pines

Condo in Pinehurst

Home in Southern Pines

Cottage in Pinehurst

Other great vacation rentals in Southern Pines

Guesthouse in Southern Pines

Loft in Southern Pines

Bungalow in Southern Pines

Vacation home in Southern Pines

Condo in Southern Pines

Apartment in Southern Pines

Guesthouse in Southern Pines

Place to stay in Vass

Quick stats about vacation rentals in Southern Pines

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Southern Pines?

Are there pet-friendly vacation rentals in Southern Pines?

Are there vacation rentals with a dedicated workspace in Southern Pines?

Are there Southern Pines vacation rentals on Airbnb with pools?

Do condo rentals in Southern Pines have wifi?

Do house rentals in Southern Pines have a bbq area?

Do house rentals in Southern Pines have a gym?

Are there family-friendly house rentals in Southern Pines?

Do townhouse rentals in Southern Pines have air conditioning?

How much does it cost to stay in townhouse rentals in Southern Pines?

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