Photo by Eric Mondres

Search Vacation Homes in Southern Pines

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 336 Vacation Homes in Southern Pines with updated reviews, rates, and availability.

Large House w/ Private pool - perfect for Golfing Groups (12) beds
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (73)
"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
Beautiful 1920's Craftsman-Downtown Southern Pines
Exterior

Beautiful 1920's Craftsman-Downtown Southern Pines

10.0 out of 10, Exceptional, (63)
"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 514
AED 1,164 total
includes taxes & fees
12 May - 13 May
Beautiful 1920's Craftsman-Downtown Southern Pines
Golf front home with 8 beds
Exterior

Golf front home with 8 beds

9.8 out of 10, Exceptional, (141)
"2nd time we've stayed at this property and once again it was perfect for us. Well furnished and comfortable with 2 separate living areas so the kids could enjoy themselves and the adults could relax. Situated on a beautiful golf course and convenient to Pinehurst and Southern Pines."
Golf front home with 8 beds
Pinehurst Vacation House w/ pool & (9) beds
Outdoor pool

Pinehurst Vacation House w/ pool & (9) beds

10.0 out of 10, Exceptional, (131)
"The house was just as advertised and was a wonderful place to stay for my family and friends this trip. Would 100% recommend and will always stay here when coming to Pinehurst. "
Pinehurst Vacation House w/ pool & (9) beds
New! Spacious 4 BD Golf Getaway with Game Room!
Fridge, microwave, oven, stovetop

New! Spacious 4 BD Golf Getaway with Game Room!

10.0 out of 10, Exceptional, (13)
"Nice location for a week of golfing in Pinehurst. "
New! Spacious 4 BD Golf Getaway with Game Room!
Oasis: Walk to Village, Heated Pool, Putting Green,Fire Pit, Hot Tub, 3 houses
Property grounds

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

10.0 out of 10, Exceptional, (118)
"The property is great for a couples trip which we did. Walkability to the Village is wonderful. Back yard space is enjoyable and the hot tub was great. We look forward to coming back. "
Oasis: Walk to Village, Heated Pool, Putting Green,Fire Pit, Hot Tub, 3 houses
Book GOLF with us! Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table
Fridge, microwave, oven, stovetop

Book GOLF with us! Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table

10.0 out of 10, Exceptional, (44)
"Great property clean and great location "
Book GOLF with us! Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table
Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8
Fridge, microwave, oven, stovetop

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

9.6 out of 10, Exceptional, (11)
"We had 5 adults visiting our family in Pinehurst. The house was well stocked and beds comfortable. Would stay here again."
Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8
Moonshine Cottage - Time to GOLF!
Fridge, microwave, oven, stovetop

Moonshine Cottage - Time to GOLF!

9.8 out of 10, Exceptional, (194)
"This was exactly what we needed and the owners had done a wonderful job welcoming us. We will be staying again."
Moonshine Cottage - Time to GOLF!
Ducks Landing Accommodations at Southern Pines Golf Course
Miscellaneous

Ducks Landing Accommodations at Southern Pines Golf Course

2.0 star property
10.0 out of 10, Exceptional, (3)
"Quiet, clean and relaxing! It was nice to sit out on the patio at night! Anything we needed they answered right away. Would definitely stay here again! "
Ducks Landing Accommodations at Southern Pines Golf Course
High Cotton! Completelyrenovated 3BR, 2.5BA home! 1.5 mi to the Village!
Smart TV, fireplace

High Cotton! Completelyrenovated 3BR, 2.5BA home! 1.5 mi to the Village!

10.0 out of 10, Exceptional, (31)
"This VRBO checked all the boxes for our family reunion: clean, convenient location, spacious and affordable. "
High Cotton! Completelyrenovated 3BR, 2.5BA home! 1.5 mi to the Village!
4 Bedroom Pinehurst Home with Pool and Hot Tub
Fridge, microwave, oven, stovetop

4 Bedroom Pinehurst Home with Pool and Hot Tub

9.6 out of 10, Exceptional, (44)
"Place was great, full of Pinehurst charm. We were two Dads and two teenage boys that went down for a junior golf tournament, was perfect setup & location is excellent."
4 Bedroom Pinehurst Home with Pool and Hot Tub
600 Linden: 8 BR, 5.5 BA House in Pinehurst, Sleeps 20
Pool

600 Linden: 8 BR, 5.5 BA House in Pinehurst, Sleeps 20

9.8 out of 10, Exceptional, (60)
"Had a company get together at the property. Great location and plenty of space."
600 Linden: 8 BR, 5.5 BA House in Pinehurst, Sleeps 20
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Outdoor dining

The 19th Hole: Sleeps 10. Pool Table, Fire Pit

10.0 out of 10, Exceptional, (32)
"House was perfect! We would definitely come back!"
The price is AED 826
AED 1,838 total
includes taxes & fees
18 May - 19 May
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Fridge, microwave, oven, stovetop

Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

10.0 out of 10, Exceptional, (39)
"The house is perfectly located for a Pine Needles, Mid Pines, Southern Pines golf trip. The town of Southern Pines has lots of good dining options just a walk or short drive away. "
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Upstairs at the Estate - Across from SP Golf Club
Aerial view

Upstairs at the Estate - Across from SP Golf Club

10.0 out of 10, Exceptional, (30)
"We loved our weekend stay! Would definitely recommend and return! "
The price is AED 331
AED 752 total
includes taxes & fees
11 May - 12 May
Upstairs at the Estate - Across from SP Golf Club
Charming Downtown Cottage
Terrace/patio

Charming Downtown Cottage

9.8 out of 10, Exceptional, (43)
"Extremely clean, convenient without losing original charm. Quiet neighborhood, beautiful street, easy walking to restaurants shops"
The price is AED 547
AED 1,139 total
includes taxes & fees
14 May - 15 May
Charming Downtown Cottage
Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed
Terrace/patio

Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed

9.8 out of 10, Exceptional, (39)
"We enjoyed a week long vacation with our pups. Our local contact was very responsive and helpful during arrival and check-out. Convenient location and comfortable furnishings with everything we needed for a great stay! "
Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed
Million Dollar View w/ 3 masters + Peloton on Pinehurst No. 9
Terrace/patio

Million Dollar View w/ 3 masters + Peloton on Pinehurst No. 9

10.0 out of 10, Exceptional, (24)
"excellent stay all around. great property and great location."
Million Dollar View w/ 3 masters + Peloton on Pinehurst No. 9
NEW! Pinehurst Eight Sleeps 10!
Interior

NEW! Pinehurst Eight Sleeps 10!

9.6 out of 10, Exceptional, (81)
"Great place to stay for our group!"
The price is AED 571
AED 1,832 total
includes taxes & fees
21 May - 22 May
NEW! Pinehurst Eight Sleeps 10!
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.
Don't see what you're looking for?
See all available properties in Southern Pines
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southern Pines

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8
Fridge, microwave, oven, stovetop

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

9.6 out of 10, Exceptional, (11)
"We had 5 adults visiting our family in Pinehurst. The house was well stocked and beds comfortable. Would stay here again."
Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8
Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf
Interior

Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf

10.0 out of 10, Exceptional, (11)
"This location and property served our needs very well thank you!"
The price is AED 4,408
AED 5,078 total
includes taxes & fees
9 May - 10 May
Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf
52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4
Fridge, microwave, oven, stovetop

52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4

9.4 out of 10, Exceptional, (46)
"Very comfortable and clean. Nice location."
52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4
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.