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Search Vacation Homes in Southern Pines

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Compare 301 Vacation Homes in Southern Pines with updated reviews, rates, and availability.

Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
10.0 out of 10, Exceptional, (17)
"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!
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
10.0 out of 10, Exceptional, (33)
"Went for a golf weekend with the boys. Perfect house for the Pines courses. Less than a mile to Southern Pines. Five minutes from Mid Pines. Seven minutes to Talamore. 12 minutes to Pinehurst number two. Hiighly recommend and would definitely stay there again."
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
10.0 out of 10, Exceptional, (95)
"We went on a couples trip and had an amazing time. The property owner was very responsive and the location and property amenities were fantastic. Looking forward to going back. "
The price is $1,173
includes taxes & fees
$1,079 per night
Sep 24 - Sep 25
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Golfers Dream at Pinehurst No. 6 with Pool Table
10.0 out of 10, Exceptional, (34)
"This was our 2nd year in a row coming to Pinehurst. We have done VRBO both times. This house was everything we wanted. Perfect size, location, everything. Only one thing that was missing, there was no garage door opener so was kindof a pain to get out, run around through the front door and open the garage to get in and out. Other than that, loved it.will definitely stay here again."
Golfers Dream at Pinehurst No. 6 with Pool Table
Luxurious, peaceful and cozy townhome in the heart of Pinehurst
10.0 out of 10, Exceptional, (38)
"The unit was very nice and updated. It is in a perfect location. We had a problem with the AC but Andrea was quick to get it resolved. I highly recommend this condo if you are looking for a place to stay in Pinehurst "
Luxurious, peaceful and cozy townhome in the heart of Pinehurst
Irons & Woods of Pinehurst
10.0 out of 10, Exceptional, (22)
"This house was wonderful! Great location and very nice inside. Plenty of room for everyone! The updated kitchen was well stocked with everything you need. 10/10 highly recommend!"
Irons & Woods of Pinehurst
New! Epic 12 Bed Golf Vacation - Chipping Inn
2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing home to host my large family. The amenities in the house were our favorite and the home offered so many activities for all ages. We cooked while we were there and it was wonderful to have a fully stocked kitchen and plenty of fridge space with the two refrigerators. Everything was clean and it was in the perfect location. We will definitely be staying again!"
The price is $800
includes taxes & fees
$735 per night
Oct 8 - Oct 9
New! Epic 12 Bed Golf Vacation - Chipping Inn
NEW! Pinehurst Eight Sleeps 10!
9.4 out of 10, Exceptional, (65)
"The house was very nice & the neighborhood quiet. "
The price is $465
includes taxes & fees
$423 per night
Oct 7 - Oct 8
NEW! Pinehurst Eight Sleeps 10!
Golf front home with 8 beds
9.8 out of 10, Exceptional, (130)
"We had a great stay at this property. It's located right down the road from the resort and across the street from the Harness Track restaurant, the ideal place for a great breakfast before your rounds. The house was roomy and clean with plenty of bedrooms and bathrooms to accommodate the 6 golfers in our group. Also appreciated were the plentiful towels and linens, and comfortable beds. Many thanks to our host. We will certainly plan to stay at this property for our next Pinehurst golf buddies...
Golf front home with 8 beds
Pinehurst Village Vacation House w/ private pool & (8) beds
10.0 out of 10, Exceptional, (57)
"Old historic house with modern touches. Family loved the game room."
Pinehurst Village Vacation House w/ private pool & (8) beds
Stylish Residence in the Pines - 5 minutes from Pinehurst Golf!
10.0 out of 10, Exceptional, (29)
"I stayed at this property last year and it was perfect for my 4-5 day stay in Pinehurst and knew I would request the same place if I returned this year. The location to the golf courses and downtown is within a 5 minute drive. The inside of the property is immaculate and has every supply needed for an enjoyable stay. The outside patio is perfect to enjoy the peacefulness of the neighborhood. If I return next year, I will definitely attempt to secure the place again. My communication with...
Stylish Residence in the Pines - 5 minutes from Pinehurst Golf!
The Tin Cup on Pinehurst #5
9.6 out of 10, Exceptional, (29)
"We had a wonderful stay here! The property is spacious, clean and very comfortable and is just as described in the listing. The kitchen has everything you need for quick meals. It backs right up to the golf course so you can watch people playing off the tee box. Lots of space for a group if that’s what you’re looking for. It’s a quick drive to Pinehurst #2 and the village. Communication with the host was top notch.. we’ll definitely check it out again for our next visit. "
The price is $462
includes taxes & fees
$420 per night
Oct 1 - Oct 2
The Tin Cup on Pinehurst #5
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
10.0 out of 10, Exceptional, (18)
"Wonderful place for an executive retreat. Excellent communication with the owner!"
The price is $499
includes taxes & fees
$454 per night
Sep 25 - Sep 26
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
The Scotsman Cottage
10.0 out of 10, Exceptional, (25)
"This house was perfect for our family. It was super convenient to the golf courses. Our child was competing in the US Kids Worlds golf tournament at Pinehurst #5. The drive was less than 5 minutes. The house was clean and very comfortable. We will be back in the future."
The Scotsman Cottage
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
10.0 out of 10, Exceptional, (46)
"Our stay was wonderful !! The place was perfect. Clean. And so comfortable. "
The price is $299
includes taxes & fees
$272 per night
Sep 24 - Sep 25
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Contemporary Scandinavian styled home on the 7th hole of Pinehurst #1
9.8 out of 10, Exceptional, (44)
"Stayed during US Kids Golf Teens championship week. House was wonderful. It backs to hole 7 of Pinehurst 1 (short Par 3). The drive to the resort is 5 minutes door to door. The house is actually nicer than the pictures show. Master bedroom is huge with a very nice bath. Would stay here again."
Contemporary Scandinavian styled home on the 7th hole of Pinehurst #1
New Build! 5mins to Golf and the Village - 5 Bedroom & 3.5 Bath!
10.0 out of 10, Exceptional, (18)
"Very pleasant, quiet area. Nice house. Only thing needed is dressers in bedrooms. No place to put clothes, except shelves in closet."
New Build! 5mins to Golf and the Village - 5 Bedroom & 3.5 Bath!
Hot Tub Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
10.0 out of 10, Exceptional, (2)
"Enjoyed our stay over the Christmas holiday. We choose the house based on its location. It’s easily walkable to downtown Southern Pines and a short drive to Pinehurst. The house is nicely decorated, bedrooms comfy and equally sized, kitchen well equipped, and the hot tub was very relaxing. The bathrooms are updated. The backyard is huge and would be a nice place to hang out in good weather. Check-out was simple. Hosts were quick to respond to communication. Great experience overall!"
The price is $230
includes taxes & fees
$209 per night
Sep 24 - Sep 25
Hot Tub Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
Southern Pines Vacation Rental w/ Deck & Grill!
10.0 out of 10, Exceptional, (9)
"We loved it! So well furnished and close to everything! Very clean and just as described."
Southern Pines Vacation Rental w/ Deck & Grill!
Isle of the Pines, 1 mile from The Village of Pinehurst!
9.2 out of 10, Wonderful, (5)
"The windows were very dirty, The living room furniture in looks good in pictures but isn’t comfortable. The house is on a semi busy hilly road with a double stripe 2 lanes so difficult to back out onto and didn’t necessarily feel safe walking dog. "
The price is $348
includes taxes & fees
$316 per night
Oct 1 - Oct 2
Isle of the Pines, 1 mile from The Village of Pinehurst!
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Other property types in Southern Pines

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
10.0 out of 10, Exceptional, (2)
"Very clean house! Check in was easy and everything was as advertised!"
The price is $303
includes taxes & fees
$275 per night
Sep 24 - Sep 25
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
10.0 out of 10, Exceptional, (17)
"Perfect home for a small group or family. Communication was excellent "
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
Beautiful 1920's Craftsman-Downtown Southern Pines
10.0 out of 10, Exceptional, (49)
"This was a very easy process for us to get in and out of the property. Great location walking distance from good times and food. Had everything we needed ready to go."
The price is $312
includes taxes & fees
$284 per night
Sep 29 - Sep 30
Beautiful 1920's Craftsman-Downtown Southern Pines
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.