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

Southern Pines Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Southern Pines vacation rentals

Property grounds

1. Loft Cottage on Ridge<br>? Short & Extended Stays?

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
9.8 out of 10, Exceptional, (42 reviews)
"The loft cottage was perfect for my visit with children's families in the area. It provided an quiet off the street place to sleep and recover from full days with grandchildren. I especially enjoyed the small second floor deck in the trees for morning coffee. I hope to stay there again when in the area!"
United States
Ted D.
The price is ￥11,253
￥23,778 total
includes taxes & fees
Sep 13 - Sep 14
Loft Cottage on Ridge<br>? Short & Extended Stays?
Exterior

2. 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, (46 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is ￥13,907
￥32,122 total
includes taxes & fees
Sep 9 - Sep 10
Upstairs at the Estate - Across from SP Golf Club
Exterior

3. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is ￥12,440
￥25,373 total
includes taxes & fees
Sep 13 - Sep 14
Walkable Cottage, Pet Friendly with Fenced Patio
Exterior

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (96 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is ￥19,423
￥47,728 total
includes taxes & fees
Sep 22 - Sep 23
Beautiful 1920's Craftsman-Downtown Southern Pines
Room

5. 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 ￥10,020
￥23,516 total
includes taxes & fees
Sep 14 - Sep 15
Located in # 6 golf community, close to First Health Moore Regional Hospital.
Apartment (3 Bedrooms) | Interior

6. Downtown Townhome; Walk to Dine & Shop on Broad St

Downtown Townhome; Walk to Dine & Shop on Broad St
3.0 star property
Southern Pines
Downtown Townhome; Walk to Dine & Shop on Broad St
Exterior detail

7. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (18 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 price is ￥14,490
￥33,273 total
includes taxes & fees
Sep 10 - Sep 11
The Cottage at Knollwood Manor
Room

8. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (58 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
The price is ￥20,672
￥46,353 total
includes taxes & fees
Sep 9 - Sep 10
Charming Downtown Cottage
Room

9. 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 ￥13,874
￥40,412 total
includes taxes & fees
Sep 9 - Sep 10
The Lucky Lie - Entire Condo in Pinehurst
Living area

10. 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 ￥6,826
￥28,617 total
includes taxes & fees
Sep 9 - Sep 10
Studio Seven at Pine Valley
Interior

11. 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, (65 reviews)
"Great stay!"
United States
Anonymous traveler
The price is ￥13,411
￥32,048 total
includes taxes & fees
Sep 9 - Sep 10
19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Private kitchen

12. 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, (52 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
The price is ￥13,565
￥32,226 total
includes taxes & fees
Sep 28 - Sep 29
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Private kitchen

13. 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, (20 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is ￥10,655
￥37,995 total
includes taxes & fees
Sep 14 - Sep 15
The McCaskill Cottage in the Village of Pinehurst!
Interior

14. 11 E Pinehurst Manor

11 E Pinehurst Manor
Pinehurst
9.4 out of 10, Exceptional, (55 reviews)
"Nice place "
United States
john w.
The price is ￥14,798
￥34,045 total
includes taxes & fees
Sep 9 - Sep 10
11 E Pinehurst Manor
Private kitchen

15. 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, (33 reviews)
"Amazing place!"
United States
Jeremy
The price is ￥11,387
￥44,047 total
includes taxes & fees
Sep 14 - Sep 15
Isle of the Pines, 1 mile from The Village of Pinehurst!
Dining

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

The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (23 reviews)
"Great stay!"
United States
Chris F.
The price is ￥13,874
￥40,587 total
includes taxes & fees
Oct 5 - Oct 6
The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Dining

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, (76 reviews)
"Wonderful stay and great experience with our host!"
United States
Matthew D.
The price is ￥17,758
￥45,325 total
includes taxes & fees
Sep 14 - Sep 15
The Perfect Lie in Pinehurst! A golfer's paradise!
Exterior detail

18. 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, (91 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 ￥12,875
￥31,271 total
includes taxes & fees
Sep 10 - Sep 11
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Private kitchen

19. Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Southern Pines
9.6 out of 10, Exceptional, (10 reviews)
"The host was very accommodating and we had a wonderful stay!The home is lovely and the host thought of everything, we wanted for nothing while we were there.The neighborhood is a great place to walk as is the downtown area!We can’t wait to visit again!"
United States
Michelle B.
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Living area

20. Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Downtown Southern Pines
9.8 out of 10, Exceptional, (29 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
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

Residence Inn by Marriott Southern Pines/Pinehurst NC

Residence Inn by Marriott Southern Pines/Pinehurst NC

10/10 Excellent
"Great location close to Pinehurst and Southern Pines shopping and restaurants."
Karen 2-night trip
Posted 1 day ago
Residence Inn by Marriott Southern Pines/Pinehurst NC

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:

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

Frequently asked questions

Are there vacation rentals in Southern Pines?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Southern Pines, or you can select a secluded option if you want a relaxing place to 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 vacation home rentals in Southern Pines?

Beautiful 1920's Craftsman-Downtown Southern Pines: Visitors like this Southern Pines vacation home rental. It is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Southern Pines is Luxury Golf Retreat - Simulator & Short Game Setup.

How many vacation rentals are there in Southern Pines?

With 86 Expedia vacation rentals, you're sure 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 Southern Pines Golf Club and Mid Pines Golf Club.

What are vacation rentals like in Southern Pines?

Vacation rentals are private accommodations you can stay in for a couple days or more in Southern Pines. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.