Photo by Eric Mondres

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Compare 281 Vacation Homes in Southern Pines with updated reviews, rates, and availability.

Beautiful 1920's Craftsman-Downtown Southern Pines
Kitchen area
Beautiful 1920's Craftsman-Downtown Southern Pines
10.0 out of 10, Exceptional, (52)
"We came into southern pines to visit friends and family. The cottage was in a great location and very clean "
The price is SAR 507
SAR 1,173 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Beautiful 1920's Craftsman-Downtown Southern Pines
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Welcome to Enchanted Escape - a beautiful 1917 bungalow and 2 tiny homes.
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
10.0 out of 10, Exceptional, (101)
"Our extended family reunion was wonderful. We all love to cook and this property has a well stocked kitchen able to accommodate cooking full meals for 12+ people and a bake off by each family. The pool and fire pit are a wonderful place to spend the day with lots of space. We loved being able to walk to town, it’s so quaint. We will definitely come back again. They have a great information booklet with instructions for everything in the house and suggestions for things to do. "
The price is SAR 1,713
SAR 4,432 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Golfers Dream at Pinehurst No. 6 with Pool Table
Spacious Living Room
Golfers Dream at Pinehurst No. 6 with Pool Table
10.0 out of 10, Exceptional, (37)
"The house is beautiful and is close to many golf courses We plan on returning annually The owners were a true delight to work with even when there seee a few problems, quickly taken care of. "
Golfers Dream at Pinehurst No. 6 with Pool Table
Peaceful Southern Pines Home w/ Pool + Yard!
Southern Pines Vacation Rental | 4BR | 3.5BA | 2,560 Sq Ft | Stairs Required
Peaceful Southern Pines Home w/ Pool + Yard!
9.6 out of 10, Exceptional, (28)
"Nice place, close to golf, shopping, and dining. Would stay there again. Plenty of space inside and out. "
Peaceful Southern Pines Home w/ Pool + Yard!
Upstairs at the Estate - Across from SP Golf Club
Upstairs at the Estate - Across from SP Golf Club
9.8 out of 10, Exceptional, (20)
"Great location for this well appointed and super comfortable property!"
The price is SAR 346
SAR 780 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Upstairs at the Estate - Across from SP Golf Club
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
bright and airy open concept living space
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
10.0 out of 10, Exceptional, (21)
"A group of ladies attending golf camp . The property was well worth the money. We enjoyed the peace and quiet neighborhood. "
The price is SAR 845
SAR 1,888 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Idyllic Pinehurst Home, Near Golf Course!
Pinehurst Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,600 Sq Ft
Idyllic Pinehurst Home, Near Golf Course!
9.6 out of 10, Exceptional, (15)
"Nice VRBO. My only suggestion would be a new couch for the living room. "
Idyllic Pinehurst Home, Near Golf Course!
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
Interior
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
10.0 out of 10, Exceptional, (18)
"Everything about this stay has been amazing. The communication with the host was great. He is so friendly and accommodating. This house is just spectacular. Its right on the 9th hole of Pinehurst No. 5 which was the icing on the cake. The finishes in this home are lovely and the simulator room took it to another level. If you are looking for a rental that is conveniently located, modern and has ALL of the amenities... this is it!! We'll be back!"
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
New! Epic 12 Bed Golf Vacation - Chipping Inn
New! Epic 12 Bed Golf Vacation - Chipping Inn
2.5 star property
10.0 out of 10, Exceptional, (2)
"House was well pointed. Neat design and very comfortable grade for a group on a golf trip."
New! Epic 12 Bed Golf Vacation - Chipping Inn
Gorgeous Pinehurst No 6 Home w/ Two Patios!
Living area
Gorgeous Pinehurst No 6 Home w/ Two Patios!
10.0 out of 10, Exceptional, (24)
"The home was “as advertised “ and we all had a great time!!"
Gorgeous Pinehurst No 6 Home w/ Two Patios!
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Living area
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
10.0 out of 10, Exceptional, (3)
"Beautiful home. Location was peaceful and quiet. "
The price is SAR 432
SAR 1,136 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Palmer House - Pet Friendly
Palmer House - Pet Friendly
9.8 out of 10, Exceptional, (14)
"We enjoyed our stay at the Palmer House this past weekend. It is a comfortable, well laid out, and well equipped house. The shared bathroom toilet is missing a nut to secure the toilet seat. This allowed the seat to slide when used but we were still able to use the unit. The light on the garage door opener was burned out so we swapped it out with a bulb from the light fixture over the dining area table. It seems odd this was the only light switch we could find even though there a fluorescent...
Palmer House - Pet Friendly
The Mulligan!
Game room
The Mulligan!
9.8 out of 10, Exceptional, (14)
"The house was wonderful. It accommodated all of us quite well."
The price is SAR 406
SAR 1,690 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
The Mulligan!
Irons & Woods of Pinehurst
Irons & Woods of Pinehurst
10.0 out of 10, Exceptional, (26)
"This is a great home. Clean, neat, many amenities. Large rooms, great family room and outdoor space in the back. Close to all the courses, restaurants. Very pleased and would definitely stay here again. And super responsive, helpful, and accommodating host."
Irons & Woods of Pinehurst
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Exterior
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
10.0 out of 10, Exceptional, (34)
"Great location near downtown Southern Pines, spacious with lovely screened porch. Would stay here again. "
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Downtown So. Pines - sleeps 8, walk to town.
Fire Pit
Downtown So. Pines - sleeps 8, walk to town.
10.0 out of 10, Exceptional, (12)
"Great place to stay for our family. Grandkids loved the large yard. Place looked recently remodeled. Very clean; comfortable beds; good kitchen. Definitely would stay again."
The price is SAR 391
SAR 1,111 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Downtown So. Pines - sleeps 8, walk to town.
Cottage on Ridge- Short & Extended Stays
Cottage on Ridge- Short & Extended Stays
9.8 out of 10, Exceptional, (20)
"Nice little place, not far from downtown Southern Pines "
The price is SAR 353
SAR 694 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
Cottage on Ridge- Short & Extended Stays
Modern home, 4 bed/2 bath, Grill, Dog friendly!
Dining
Modern home, 4 bed/2 bath, Grill, Dog friendly!
9.6 out of 10, Exceptional, (13)
"We had a great time staying here. The house was well-kept and comfortable, and the host’s communication was excellent. Everything went smoothly, and we appreciated the attention to detail. Looking forward to staying here again on our next trip!"
Modern home, 4 bed/2 bath, Grill, Dog friendly!
Loft Cottage on Ridge<br>? Short & Extended Stays?
Loft Cottage on Ridge<br>? Short & Extended Stays?
10.0 out of 10, Exceptional, (13)
"Meghan was a wonderful host! She responded to every question very quickly. We enjoyed our stay. The loft cottage was adorable and in a perfect location. I would definitely stay here again when I come back to North Carolina! Super cute decor….. "
The price is SAR 233
SAR 526 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Loft Cottage on Ridge<br>? Short & Extended Stays?
NEW Pinehurst Golf Home - 5 mins from Course 1-9
Living area
NEW Pinehurst Golf Home - 5 mins from Course 1-9
10.0 out of 10, Exceptional, (51)
"house was clean and check in/out was easy"
NEW Pinehurst Golf Home - 5 mins from Course 1-9
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southern Pines

Peaceful Southern Pines Home w/ Pool + Yard!
Southern Pines Vacation Rental | 4BR | 3.5BA | 2,560 Sq Ft | Stairs Required
Peaceful Southern Pines Home w/ Pool + Yard!
9.6 out of 10, Exceptional, (28)
"Nice place, close to golf, shopping, and dining. Would stay there again. Plenty of space inside and out. "
Peaceful Southern Pines Home w/ Pool + Yard!
Cottage on Ridge- Short & Extended Stays
Cottage on Ridge- Short & Extended Stays
9.8 out of 10, Exceptional, (20)
"Nice little place, not far from downtown Southern Pines "
The price is SAR 353
SAR 694 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
Cottage on Ridge- Short & Extended Stays
Loft Cottage on Ridge<br>? Short & Extended Stays?
Loft Cottage on Ridge<br>? Short & Extended Stays?
10.0 out of 10, Exceptional, (13)
"Meghan was a wonderful host! She responded to every question very quickly. We enjoyed our stay. The loft cottage was adorable and in a perfect location. I would definitely stay here again when I come back to North Carolina! Super cute decor….. "
The price is SAR 233
SAR 526 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Loft Cottage on Ridge<br>? Short & Extended Stays?
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.