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Compare 280 Vacation Homes in Southern Pines with updated reviews, rates, and availability.

NEW! Pinehurst Eight Sleeps 10!
Primary Bedroom with en suite

NEW! Pinehurst Eight Sleeps 10!

9.6 out of 10, Exceptional, (73)
"What a beautiful place!!! It’s just as gorgeous as the photos! I highly recommend this property! I made a booking blunder and the host went above and beyond to help me get it fixed. The communication was amazing throughout the stay. The house was stocked with everything you would need. The location is great! I would definitely book this property again. "
The price is AED 424
AED 1,683 total
includes taxes & fees
14 Jan - 15 January 2025
NEW! Pinehurst Eight Sleeps 10!
Beautiful 1920's Craftsman-Downtown Southern Pines
Kitchen area

Beautiful 1920's Craftsman-Downtown Southern Pines

10.0 out of 10, Exceptional, (55)
"Location of this traditional home in So Pines was great. Beds were very comfy and our host was attentive to our every need. Would definitely stay again. "
The price is AED 496
AED 1,151 total
includes taxes & fees
31 Dec - 1 January 2025
Beautiful 1920's Craftsman-Downtown Southern Pines
Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table
Spacious Living Room

Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table

10.0 out of 10, Exceptional, (40)
"The house was clean, well appointed and comfortable. It was the perfect spot for our girls weekend!"
Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table
Oasis: Walk to Village, Heated Pool, Putting Green,Fire Pit, Hot Tub, 3 houses,
Welcome to Enchanted Escape - a beautiful 1917 bungalow and 2 tiny homes.

Oasis: Walk to Village, Heated Pool, Putting Green,Fire Pit, Hot Tub, 3 houses,

10.0 out of 10, Exceptional, (104)
"Great"
Oasis: Walk to Village, Heated Pool, Putting Green,Fire Pit, Hot Tub, 3 houses,
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!

9.4 out of 10, Exceptional, (30)
"My family and I thoroughly enjoyed our stay here. Pristine, spacious and comfortable. "
Peaceful Southern Pines Home w/ Pool + Yard!
Putt in the Pines
Living area

Putt in the Pines

9.8 out of 10, Exceptional, (10)
"House was great for our stay during USKids tournament. Great location, central to all the courses. Quick response from manager. Comfy home and super clean."
The price is AED 400
AED 1,192 total
includes taxes & fees
24 Dec - 25 Dec
Putt in the Pines
North Carolina Home ~ 2 Mi to Pinehurst Resort
Pinehurst Vacation Rental | 4BR | 3.5BA | 2,700 Sq Ft | 5 Steps Required

North Carolina Home ~ 2 Mi to Pinehurst Resort

10.0 out of 10, Exceptional, (11)
"This beautiful home is well-appointed and just as described. Everything was clean and fresh and the decor is lovely. The layout accommodated our group of lady golfers perfectly. The neighborhood is very nice and quiet and conveniently located to the village. We would definitely return! "
North Carolina Home ~ 2 Mi to Pinehurst Resort
Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines
Exterior

Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines

Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines
Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village
Private kitchen

Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village

9.8 out of 10, Exceptional, (19)
"Hreat timevplenty of room Cool house"
Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village
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, (25)
"We absolutely loved this house!!! We were in town for a wedding and it was a perfect location to get to everything!! I just wish we could have been able to spend more time there, it is a perfect place to stay, hope we can get back sometime! Highly recommend!!!"
The price is AED 826
AED 1,842 total
includes taxes & fees
1 Jan - 2 January 2025
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays

10.0 out of 10, Exceptional, (21)
"Nice little place, not far from downtown Southern Pines "
Cottage on Ridge- Short & Extended Stays
#6 near Village w/ King * Pinehurst Brews and Snooze * EV Charger * 4 Beds
Open the doors to the decks to let the fresh scent of pine trees in!

#6 near Village w/ King * Pinehurst Brews and Snooze * EV Charger * 4 Beds

10.0 out of 10, Exceptional, (30)
"Everything we needed in the process and stay "
#6 near Village w/ King * Pinehurst Brews and Snooze * EV Charger * 4 Beds
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Living area

Beautiful 1 Bed Condo on Pinehurst Course No.5!

10.0 out of 10, Exceptional, (6)
"Cozy and comfortable. Great location. Will stay here again."
The price is AED 386
AED 901 total
includes taxes & fees
3 Jan - 4 January 2025
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Double Bronze. Fairway home with Golf Cart!
Living area

Double Bronze. Fairway home with Golf Cart!

9.4 out of 10, Exceptional, (34)
"We didn’t want to check out! Very homey and great neighborhood! The golf cart was a nice touch although this isn’t really what I would call a golf cart community so we really couldn’t drive it too far but took it for a spin and found a path to take it up to the resort without getting on main roads. "
The price is AED 369
AED 1,384 total
includes taxes & fees
7 Jan - 8 January 2025
Double Bronze. Fairway home with Golf Cart!
The Chatham House-Pinehurst.....
Welcome!

The Chatham House-Pinehurst.....

10.0 out of 10, Exceptional, (34)
"Beautiful location and very comfortable place to stay! We thoroughly enjoyed the week!"
The Chatham House-Pinehurst.....
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, (19)
"We came down for the US Kids golf tournament. This was perfect for our family. Simulator, games, hot tub, and spacious. We had some difficulty getting the simulator started and the communication with the owner was great! Quick response! We will definitely stay here again!"
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst
Pool

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst

2.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed here for a show at Carolina Horse Park. My only hesitation in leaving this review is we may not get to reserve it again. It was just perfect (they even left us sunscreen!). "
Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst
Newly updated home near Pinehurst resort & No. 2 clubhouse!
Exterior Elevation

Newly updated home near Pinehurst resort & No. 2 clubhouse!

10.0 out of 10, Exceptional, (27)
"Such a great property! We loved this house. Great location and very clean. We will definitely be back !"
Newly updated home near Pinehurst resort & No. 2 clubhouse!
Large House w/ Private pool - perfect for Golfing Groups (12) beds
Pool

Large House w/ Private pool - perfect for Golfing Groups (12) beds

10.0 out of 10, Exceptional, (69)
"We enjoyed staying at this house, lots of activities for children between pool and ping pong! We hope to stay here again!"
Large House w/ Private pool - perfect for Golfing Groups (12) beds
Luxurious, peaceful and cozy townhome in the heart of Pinehurst
Spacious Living Room

Luxurious, peaceful and cozy townhome in the heart of Pinehurst

10.0 out of 10, Exceptional, (47)
"The stay was great! Very clean property! Kitchen was well appointed and there were plenty of linens (extra bath towels and blankets). My daughter played Midpines and Pine Needles, location of property was only about 5 minutes from courses. "
Luxurious, peaceful and cozy townhome in the heart of Pinehurst
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

Beautiful 1920's Craftsman-Downtown Southern Pines
Kitchen area

Beautiful 1920's Craftsman-Downtown Southern Pines

10.0 out of 10, Exceptional, (55)
"Location of this traditional home in So Pines was great. Beds were very comfy and our host was attentive to our every need. Would definitely stay again. "
The price is AED 496
AED 1,151 total
includes taxes & fees
31 Dec - 1 January 2025
Beautiful 1920's Craftsman-Downtown 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!

9.4 out of 10, Exceptional, (30)
"My family and I thoroughly enjoyed our stay here. Pristine, spacious and comfortable. "
Peaceful Southern Pines Home w/ Pool + Yard!
Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines
Exterior

Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines

Charming 4-bedroom, Pet Friendly House in 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.