A dense forest of tall pine trees with a clear sky.

Southern Pines Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Southern Pines holiday rentals

A modern living room with a wooden floor, a leopard print rug, a white console table with a lamp, and a large plant.

1. Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays
Southern Pines
9.8 out of 10, Exceptional, (50 reviews)
"Convenient, clean...a really cute place to stay."
United States
Jeffrey S.
The price is HK$612
HK$1,330 total
includes taxes & fees
21 Oct - 22 Oct
Cottage on Ridge- Short & Extended Stays
A bedroom with a bed, a desk, a chair, a ceiling fan, and a view through a glass door.

2. Located in # 6 golf community, close to First Health Moore Regional Hospital.

Located in # 6 golf community, close to First Health Moore Regional Hospital.
Pinehurst
10.0 out of 10, Exceptional, (79 reviews)
"Nice cozy suite, just right for two people. Wife and I were in town for a nearby wedding and stayed here. Excellent place to stay."
United States
Thomas M.
The price is HK$534
HK$1,268 total
includes taxes & fees
31 Oct - 1 Nov
Located in # 6 golf community, close to First Health Moore Regional Hospital.
A single-story house with a gray exterior, white trim, and a front porch.

3. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is HK$728
HK$1,400 total
includes taxes & fees
7 Oct - 8 Oct
Walkable Cottage, Pet Friendly with Fenced Patio
A modern kitchen with a stainless steel refrigerator, white cabinetry, and a marble countertop.

4. 19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Pinehurst
8.8 out of 10, Excellent, (68 reviews)
"Great location and plenty of room for the two of us. Dog friendly neighborhood and very walkable. Nice work area off the dining room. Kitchen was stocked pretty well from a dishes/pans/glasses perspective. The only issues were: no hangers in any of the closets, no hair dryer, and the floors were really dirty (ruined a couple pairs of socks) so needed to wear shoes all the time."
United States
sheri m.
The price is HK$675
HK$1,622 total
includes taxes & fees
11 Oct - 12 Oct
19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
A modern bedroom with a bed, a desk, and a balcony with a chair.

5. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (65 reviews)
"Always a wonderful stay!"
United States
Whitney S.
The price is HK$706
HK$2,066 total
includes taxes & fees
2 Nov - 3 Nov
The Lucky Lie - Entire Condo in Pinehurst
A modern kitchen with a double sink, a coffee maker, and a variety of snacks on the counter.

6. Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (54 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
The price is HK$738
HK$1,711 total
includes taxes & fees
2 Nov - 3 Nov
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

7. Isle of the Pines, 1 mile from The Village of Pinehurst!

Isle of the Pines, 1 mile from The Village of Pinehurst!
Pinehurst
10.0 out of 10, Exceptional, (37 reviews)
"Amazing place!"
United States
Jeremy
The price is HK$778
HK$2,493 total
includes taxes & fees
12 Oct - 13 Oct
Isle of the Pines, 1 mile from The Village of Pinehurst!
A living room with a sofa, armchair, coffee table, and a view through a glass door to the outside.

8. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.6 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Lauren
The price is HK$381
HK$1,495 total
includes taxes & fees
7 Oct - 8 Oct
Studio Seven at Pine Valley
A modern kitchen with a white island, yellow bar stools, stainless steel appliances, and large windows with curtains.

9. The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
Pinehurst
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
The price is HK$785
HK$2,173 total
includes taxes & fees
2 Nov - 3 Nov
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

10. The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
10.0 out of 10, Exceptional, (22 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is HK$627
HK$2,065 total
includes taxes & fees
2 Nov - 3 Nov
The McCaskill Cottage in the Village of Pinehurst!
A two-story house with a white exterior, a brick chimney, and a covered porch.

11. Upstairs at the Estate - Across from SP Golf Club

Upstairs at the Estate - Across from SP Golf Club
Southern Pines
10.0 out of 10, Exceptional, (47 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is HK$644
HK$1,538 total
includes taxes & fees
7 Oct - 8 Oct
Upstairs at the Estate - Across from SP Golf Club
A dining area with a poker table, chairs, a hanging light fixture, and a view of the outside through large windows.

12. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Pinehurst
9.4 out of 10, Exceptional, (19 reviews)
"Great place for a short golf getaway "
United States
Jay G.
The price is HK$643
HK$2,597 total
includes taxes & fees
19 Oct - 20 Oct
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
A house with a front porch, steps leading to a green door, and a welcome mat.

13. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (19 reviews)
"This is a favorite place for us to stay when in Southern Pines. It is lovely, comfortable, the host is very helpful and the location is great. "
United States
Tracey W.
The Cottage at Knollwood Manor
A dining area with a wooden table and chairs, a hanging light fixture, and wall-mounted artwork.

14. The Mulligan Manor - 1BR/1BA Condo in Pinehurst

The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Chris F.
The Mulligan Manor - 1BR/1BA Condo in Pinehurst
A modern kitchen with a dining area, a flat-screen TV, and a coffee maker.

15. To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (93 reviews)
"I would highly recommend staying here when visiting Pinehurst and Southern Pines. It was one of the best VRBO experiences we have enjoyed."
United States
Jenny I.
The price is HK$824
HK$1,800 total
includes taxes & fees
26 Oct - 27 Oct
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

16. Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit

Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit
Pinehurst
10.0 out of 10, Exceptional, (13 reviews)
"Great stay!"
United States
Amanda B.
The price is HK$636
HK$2,084 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a large window with a view of the outside.

17. The Perfect Lie in Pinehurst! A golfer's paradise!

The Perfect Lie in Pinehurst! A golfer's paradise!
Pinehurst
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay and great experience with our host!"
United States
Matthew D.
The price is HK$911
HK$2,315 total
includes taxes & fees
13 Oct - 14 Oct
The Perfect Lie in Pinehurst! A golfer's paradise!
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

18. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (59 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
The price is HK$1,052
HK$2,360 total
includes taxes & fees
11 Oct - 12 Oct
Charming Downtown Cottage
A modern building with a sloped roof and a balcony.

19. Walking distance to The Pinehurst Clubhouse

Walking distance to The Pinehurst Clubhouse
Pinehurst
9.8 out of 10, Exceptional, (77 reviews)
"We enjoyed our little getaway. Great location and comfortable rooms! "
United States
Angela D.
The price is HK$957
HK$2,190 total
includes taxes & fees
19 Oct - 20 Oct
Walking distance to The Pinehurst Clubhouse
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

20. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (42 reviews)
"Great location to get to all of the golf courses we played. Plenty of room for the 6 of us. Host very attentive."
United States
James N.
The price is HK$1,110
HK$3,924 total
includes taxes & fees
12 Oct - 13 Oct
The Mulligan!
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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Top Southern Pines Hotel Reviews

Holiday Inn Express Hotel & Suites Southern Pines by IHG

Holiday Inn Express Hotel & Suites Southern Pines by IHG

10/10 Excellent
"the property is fairy old, but it is maintained in spite of it."
Mary 1-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites Southern Pines by IHG

Find out more about Southern Pines

Search for holiday rentals in Southern Pines on Expedia! You can easily find your home rentals, villas, holiday apartments in Southern Pines using one of the methods below:

  • View our selection of featured holiday rentals in Southern Pines
  • Use the map to find apartments and other holiday homes in the Southern Pines neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southern Pines while they last

Look no further and take a look at our great range of rental properties in Southern Pines!

Frequently asked questions

Are there holiday rentals in Southern Pines?

Yes, there are holiday rentals close to the most popular sights in Southern Pines, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Southern Pines. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Southern Pines has to offer?

Simulator & Unbeatable Golf Experience On 2 Acres!: This highly rated holiday home rental in Southern Pines offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Southern Pines is Beautiful 1920's Craftsman-Downtown Southern Pines.

How many holiday rentals are there in Southern Pines?

With 88 Expedia holiday rentals, you're guaranteed to find just the right place for your Southern Pines stay.

What can I see and do in Southern Pines?

Cultural attractions include Campbell House Galleries, whereas Reservoir Park is a spot to enjoy nature. Other places in town to visit include Mid Pines Golf Club and Pine Needles Golf Club.

What are holiday rentals like in Southern Pines?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southern Pines. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.