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Southern Pines Vacation Rentals

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Vacation Rentals in Southern Pines

Charming, newly updated Downtown Cottage
Outdoor dining
Charming, newly updated Downtown Cottage
9.8 out of 10, Exceptional, (26)
"Great location. Close walking distance to the local eateries and shops. We had a great time here."
The price is ￥23,363
￥48,813 total
includes taxes & fees
Jun 1 - Jun 2
Charming, newly updated Downtown Cottage
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
Property grounds
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
10.0 out of 10, Exceptional, (16)
"Super quiet, very comfy and cozy 😊! The only problem we had, was having to go back to our stressful lives 😂. Definitely will come back?"
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
Peaceful Southern Pines Home w/ Pool + Yard!
Pool
Peaceful Southern Pines Home w/ Pool + Yard!
9.6 out of 10, Exceptional, (21)
"To say this property meets all of the printed expectations is a simple response. ABOVE AND BEYOND what we expected! Plenty of comfort upgrades, little notes to help at each area we may have had issues and quick response from property helped us to settle in quickly and enjoy the lovely weather and quiet neighborhood!"
Peaceful Southern Pines Home w/ Pool + Yard!
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Downtown Townhome; Walk to Dine & Shop on Broad St
Fridge, microwave, stovetop, dishwasher
Downtown Townhome; Walk to Dine & Shop on Broad St
9.8 out of 10, Exceptional, (53)
"Close to downtown Southern Pines and convenient to area activities."
Downtown Townhome; Walk to Dine & Shop on Broad St
Loft Cottage on Ridge<br>? Short & Extended Stays?
Property grounds
Loft Cottage on Ridge<br>? Short & Extended Stays?
10.0 out of 10, Exceptional, (7)
"A delightful little loft apartment in a perfect location. It had everything required for a month long stay while working in the area. Megan was fantastic with her communication, including suggestions for places to eat, drink, and things to see and do in the area. Will definitely book again when I’m back in Southern Pines."
The price is ￥11,290
￥23,614 total
includes taxes & fees
Jun 3 - Jun 4
Loft Cottage on Ridge<br>? Short & Extended Stays?
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Fridge, microwave, oven, stovetop
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 ￥18,032
￥47,432 total
includes taxes & fees
Jun 2 - Jun 3
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Beautiful 1920's Craftsman-Downtown Southern Pines
Exterior
Beautiful 1920's Craftsman-Downtown Southern Pines
10.0 out of 10, Exceptional, (44)
"Would definitely stay here again"
The price is ￥21,952
￥50,019 total
includes taxes & fees
Jun 1 - Jun 2
Beautiful 1920's Craftsman-Downtown Southern Pines
52 Longleaf - Rented during 2024 Open
Fridge, microwave, oven, stovetop
52 Longleaf - Rented during 2024 Open
9.4 out of 10, Exceptional, (36)
"Very quiet and cozy townhouse no amenities such as pool or guest house but my stay didn't require that. Enjoyed the serenity and was a good place to enjoy the unique North Carolina countryside."
52 Longleaf - Rented during 2024 Open
Mystical Cottage in Southern Pines
Pool
Mystical Cottage in Southern Pines
9.8 out of 10, Exceptional, (37)
"If I needed to escape again in an adorable spot with great wi-fi, a couple of friendly dogs and a place to clear my mind near great golf - this is the lace to go. The pool was refreshing and the get away was a slice of heaven. Thank you Alan!"
The price is ￥24,931
￥40,188 total
includes taxes & fees
Jun 30 - Jul 1
Mystical Cottage in Southern Pines
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course
Interior
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course
10.0 out of 10, Exceptional, (29)
"The stay was wonderful. Tyler was such a great host. We will certainly stay here again!"
The price is ￥82,320
￥152,475 total
includes taxes & fees
Jun 2 - Jun 3
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course
Cottage on Ridge- Short & Extended Stays
1 bedroom, desk, travel crib, WiFi
Cottage on Ridge- Short & Extended Stays
10.0 out of 10, Exceptional, (15)
"Cute place and perfect for an overnight stay in the area. The cottage had everything we needed, except for soap in the shower. Would stay there again, if in the area."
The price is ￥14,426
￥28,789 total
includes taxes & fees
Jun 5 - Jun 6
Cottage on Ridge- Short & Extended Stays
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard
Property grounds
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard
9.8 out of 10, Exceptional, (38)
"My husband and I stayed at the castle for 4 days, and I could have stayed for another 4. It was so relaxing, the hot tub was great, the hanging bed was the perfect place to sit outside on and read a book, and the bathroom was incredible! The bed in the downstairs bedroom was really comfortable, and you really will want for nothing here. It’s walking distance to everything, shops, restaurants, sit by the train tracks and grab some ice cream was very nice. The house has a very relaxing vibe to it...
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard
Modern Luxury 5BR House in Downtown Southern Pines
Private kitchen | Fridge, microwave, oven, stovetop
Modern Luxury 5BR House in Downtown Southern Pines
10.0 out of 10, Exceptional, (6)
"Family and friends gathering for southern Pines wedding. Two blocks from our venue and everything was in order. Large spacious area/great room /kitchenfor the family to gather. Lots of bedroom space all very clean and tidy."
The price is ￥45,472
￥109,352 total
includes taxes & fees
Jun 2 - Jun 3
Modern Luxury 5BR House in Downtown Southern Pines
Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
Interior
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 ￥23,520
￥44,155 total
includes taxes & fees
Jun 4 - Jun 5
Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
A Cinderella Story -Downtown Southern Pines
Fridge, microwave, oven, stovetop
A Cinderella Story -Downtown Southern Pines
10.0 out of 10, Exceptional, (25)
"The cottage was even better than the pictures online! The entire process was extremely smooth and couldn't have asked for a better location. The food recommendations provided were all great and will definitely look to stay here again next time we're in the area"
A Cinderella Story -Downtown Southern Pines
The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!
Private kitchen
The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!
10.0 out of 10, Exceptional, (4)
"Very nicely remodeled and decorated. Water and snacks upon arrival. Even shower amenities in the bathroom. Super clean and comfortable. I don't know if it was just me, but the digital key pad was a little tricky to initially light up to see the numbers. The only feedback I have to give is to include information about the other rentals on the property and to mark designated areas for parking for each rental. When I pulled up there were two cars in the driveway, spread out, taking up most of the...
The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!
"Peace On Wheels" Sleeps 4 Comfortably w/Outside Entertainment
Private kitchen
"Peace On Wheels" Sleeps 4 Comfortably w/Outside Entertainment
"Peace On Wheels" Sleeps 4 Comfortably w/Outside Entertainment
The Pinecone Cottage - a Southern Pines escape
Interior
The Pinecone Cottage - a Southern Pines escape
The Pinecone Cottage - a Southern Pines escape
Cozy Southern Pines Retreat 1 Mi to Downtown!
Interior
Cozy Southern Pines Retreat 1 Mi to Downtown!
3.5 star property
Cozy Southern Pines Retreat 1 Mi to Downtown!
Fore Seasons – Unbeatable Golf Experience!
Smart TV, fireplace
Fore Seasons – Unbeatable Golf Experience!
9.8 out of 10, Exceptional, (20)
"It was the perfect stay for our golf party. 12 guys on a golf trip and everybody was happy - that’s hard to do! The golf simulator and chipping area in the back yard was a huge hit."
Fore Seasons – Unbeatable Golf Experience!
Don't see what you're looking for?
See all available properties in 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.

Other types of properties in Southern Pines you may be interested in

Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
Outdoor banquet area
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
2.0 star property
6.6 out of 10, (699)
"Being renovated but was ok for my needs"
The price is ￥11,062
￥12,169 total
includes taxes & fees
Jul 1 - Jul 2
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
In-room safe, desk, laptop workspace, iron/ironing board
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
2.5 star property
7.6 out of 10, Good, (823)
"Great value for the price. Only downfall was the AC didn't cool very well."
The price is ￥13,660
￥15,025 total
includes taxes & fees
Jun 7 - Jun 8
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
In-room safe, desk, laptop workspace, blackout drapes
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (698)
"The room was clean and the breakfast was good. Everyone on the staff was friendly and helpful. It is better than similar hotels in the area where we have stayed."
The price is ￥18,502
￥20,352 total
includes taxes & fees
Jul 1 - Jul 2
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
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.

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
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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?

Charming, newly updated Downtown Cottage: Visitors like this Southern Pines vacation home rental. It is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. Other favorite homes for rent in Southern Pines are ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK! and Loft Cottage on Ridge
? Short & Extended Stays?.

How many vacation rentals are there in Southern Pines?

With 111 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?

Explore the area and cultural attractions such as Seagrove Pottery of the Sandhills, or visit a family-friendly sight such as Carolina Horse Park. Other places in town to visit include Pine Needles Golf Club and Pinehurst No. 9.

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.

Recent reviews of Southern Pines properties
Expedia verified reviews

Mystical Cottage in Southern Pines

Mystical Cottage in Southern Pines

5/5 Excellent
Peaceful and Convenient
"If I needed to escape again in an adorable spot with great wi-fi, a couple of friendly dogs and a place to clear my mind near great golf - this is the lace to go. The pool was refreshing and the get away was a slice of heaven. Thank you Alan!"
A verified traveler stayed at Mystical Cottage in Southern Pines
Posted 2 days ago
Mystical Cottage in Southern Pines