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 10 – 17

$91 per night

Guest favorite

Home in Pinehurst

4.98 out of 5 average rating, 656 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 4 – 11

$147 per night

Guest favorite

Apartment in Southern Pines

4.97 out of 5 average rating, 175 reviews

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

Weekend Breakfast for Two Included Sat & Sun! Welcome to the Fox Den Suite at Tanglewood Farm B&B! 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, rated as one of America's best small towns to live (Newsmax). Enjoy local breweries, shops, amazing restaurants and over 100 beautiful golf courses.

Oct 29 – Nov 5

$126 per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 138 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!

Oct 11 – 18

$141 per night

Guest favorite

Farm stay in Southern Pines

4.98 out of 5 average rating, 123 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.

Oct 30 – Nov 6

$116 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

Nov 29 – Dec 6

$76 per night

Guest favorite

Guest suite in Southern Pines

4.86 out of 5 average rating, 139 reviews

The Suite Life - In-Law Apt, Private Entry, Fenced

Renovated, pet friendly in-law suite (downstairs unit) with a private entrance and no shared living space to the upstairs. Large fenced yard, and 1 mile to downtown So Pines, 6 miles to Pinehurst Resort, king size bedroom, full sleeper sofa, Keurig, a new kitchenette with oven, microwave, full size refrigerator, 50in Amazon Fire TV to link your accounts. A washer/dryer make it great for short term leases! The Suite also has a separate thermostat/A/C. Looking forward to hosting you!

Sep 27 – Oct 4

$87 per night

Guest favorite

Guest suite in Southern Pines

4.96 out of 5 average rating, 157 reviews

Studio in the Pines ~ Minutes to downtown SoPines!

Surprisingly spacious, exceptionally clean, and completely private, this studio boasts everything a savvy traveler needs and more! Located minutes from downtown Southern Pines and from a plethora of world-class golf courses, restaurants, and shopping, this is the perfect space whether you're in town for a night or for a week. Easy commute to Ft. Bragg. Kevin & Chelsea (the hosts) live in the attached main house, but this studio is completely separated giving you plenty of privacy!

Sep 3 – 10

$87 per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 143 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!

Mar 30 – Apr 6

$114 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.

May 15 – 22

$140 per night

Guest favorite

Guest suite in Southern Pines

4.95 out of 5 average rating, 220 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.

Jul 28 – Aug 4

$85 per night

Guest favorite

Bungalow in Southern Pines

4.96 out of 5 average rating, 226 reviews

Delightful Bungalow in Historic Downtown

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.

Nov 20 – 27

$109 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

Cottage in Pinehurst

4.93 out of 5 average rating, 242 reviews

Water Oaks Cottage - Near Pinehurst Country Club

Jul 4 – 11

$128 per night

Guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 117 reviews

World Class Golf* Hot Tub *Southern Pines

Nov 18 – 25

$292 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!

Mar 6 – 13

$118 per night

Guest favorite

Guesthouse in Carthage

4.99 out of 5 average rating, 151 reviews

Charming 1 bedroom guesthouse on 4 acres, hot tub

Nov 2 – 9

$121 per night

Superhost

Condo in Pinehurst

4.81 out of 5 average rating, 105 reviews

SWalking distance to PCC. Wonderful Views. 1b1b #5

Jun 28 – Jul 5

$94 per night

Guest favorite

Condo in Pinehurst

4.94 out of 5 average rating, 191 reviews

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

May 30 – Jun 6

$106 per night

Guest favorite

Home in Southern Pines

5.0 out of 5 average rating, 11 reviews

Place beyond the Pines - Walk to downtown

Oct 27 – Nov 3

$115 per night

Guest favorite

Apartment in Southern Pines

5.0 out of 5 average rating, 18 reviews

Private&Comfortable Studio for 2 in Southern Pines

Oct 13 – 20

$90 per night

Show all

Other great vacation rentals in Southern Pines

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 5 – 12

$115 per night

Guest favorite

Guesthouse in Southern Pines

5.0 out of 5 average rating, 13 reviews

Charming Getaway Carriage House with pool

Oct 23 – 30

$90 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

Jul 15 – 22

$113 per night

Guest favorite

Condo in Southern Pines

5.0 out of 5 average rating, 12 reviews

Golf Front Longleaf Condo2BR/2BA

Nov 20 – 27

$122 per night

Guest favorite

Guesthouse in Southern Pines

5.0 out of 5 average rating, 57 reviews

The Kensington Cottage

Jun 19 – 26

$96 per night

Guest favorite

Home in Southern Pines

4.97 out of 5 average rating, 39 reviews

Midland Pines Getaway! The "Hole Nine Yards"

Dec 8 – 15

$138 per night

Guest favorite

Home in Aberdeen

4.94 out of 5 average rating, 31 reviews

Cottage in the Pine’s

May 5 – 12

$134 per night

Guest favorite

Cabin in Southern Pines

4.97 out of 5 average rating, 38 reviews

Cloverfield Barn - Ask me about discounts!

Dec 29 – Jan 5

$122 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
$20 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 townhouse rentals in Southern Pines have wifi?
Absolutely! We offer over 20 townhouse 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 private suite rentals in Southern Pines have air conditioning?
Absolutely! We offer over 10 private suite 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 cottage rentals in Southern Pines?
Experience the best of Southern Pines with our cottage rentals, starting at about $70 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

Cottage in Pinehurst

Home in Southern Pines

Condo in Pinehurst

Guesthouse in Carthage

Condo in Pinehurst

Condo in Pinehurst

Home in Southern Pines

Apartment in Southern Pines

Other great vacation rentals in Southern Pines

Vacation home in Southern Pines

Guesthouse in Southern Pines

Condo in Southern Pines

Condo in Southern Pines

Guesthouse in Southern Pines

Home in Southern Pines

Home in Aberdeen

Cabin in Southern Pines

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 townhouse 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 private suite rentals in Southern Pines have air conditioning?

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

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