Vacation Rentals By Owner In Southern Pines, NC

Come and relax at our condo in the pines! Conveniently located near Pinehurst and Southern Pines, this 2nd floor, 1350 square foot condo unit is equipped with everything to make your visit relaxing and enjoyable. The master bedroom has a magnificent king size bed, private bath, and an entrance out to the balcony. A second bedroom has a queen size bed and private bath. Lots of room, yet provides privacy as needed. brbrSome of the most famous golf courses in the U.S. are right down the road. Talamore, Mid South Club, Mid Pines, National Club, and Pine Needles are all located along Midland Road, which is within 5 minutes of our unit. Pinehurst is about 7 miles away, and is easily accessible from Midland Road. Even if you aren’t a golfer, the charming towns of Pinehurst and Southern Pines are nearby. Antiques, shopping, and fine area restaurants are all available year-round. brbrOur unit is approximately 45 minutes from Fayetteville, where Fort Bragg (Fort Liberty) is located. Several military families have stayed at the condo during visits with their family members who serve in the military. We offer a 10% discount for military families. brbrOther interesting local attractions include the pottery district which begins about 15 miles west of Pinehurst. The Sandhills Horticultural Gardens are about 10 minutes away, Cameron antique district about 20 minutes.brbrOur unit is located on the 8th hole at Hyland Hills Golf Course. We provide everything you need for a great vacation. All linens, appliances (washer and dryer in the unit), and dinnerware are available for your use. Free Wi-Fi is also available.brbrAffordable nightly rates are our specialty. Weekdays and weekend rates are the same. We offer a rate of $99 for both weekday and weekends. Weekly rates are $700 (includes $80 cleaning fee). br Monthly rates are available upon request. There is a $80 cleaning fee. No maid service is available. Feel free to call or text me (704-651-9866) with any questions.brWe look forward to having you stay in the area. Please feel free to ask questions and let us know how we can make your Pinehurst/Southern Pines visit a memorable experience!br brbrKeywords: Condominium

Condo

Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$203.4

Welcome to The Regal Roost, a thoughtfully designed loft style apartment with attached 3 stall shedrow barn. Enjoy timeless equestrian charm with modern comfort. Situated on over 11 acres with multiple oversize paddocks complete with riding arena and hacking access to Weymouth and Walthour Moss Foundation come and escape to an equestrian dream.br -15 mins drive to Carolina Horse Parkbr-5 mins drive downtown southern Pines br-10 mins drive Pinehurst for world class golf.

The Regal Roost Equestrian Escape- horse accommodations available

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(9)

$184.22

Location - Location - Location! In the heart of Downtown and nestled at the back of the main residence, Sienna Cottage at The Shire 255 is the perfect home away from home for your next trip to Southern Pines. Fully equipped kitchen, spacious living room and table for four, this property can sleep up to four guests. Enjoy easy access from the blue stone gravel drive, as well as dedicated parking for Airbnb guests conveniently located behind the main home - with plenty of auxiliary parking if you have more than one vehicle, and street parking available in case you need it.brbrSienna is the perfect retreat for couples or traveling professionals looking to be in a lively and walkable area. When we say walking distance from downtown, we mean it! Below are a few of our favorite local spots worth checking out. brbr- 400` to The Jefferson Inn (live music on the weekends)br- 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) br- 0.2 miles to Ashtens br- 0.2 miles to The Bell Tree Tavern br- 0.3 miles to Southern Pines Growler br- 0.3 miles to So Pines Pizza br- 0.4 miles to Southern Prime Steakhouse (fancy dinner) br- 0.7 miles to Betsy`s Crepes (the best breakfast spot around, in our humble opinion) br- 0.9 miles to Sly Fox (the butter chicken dish is to die for - don`t take my word for it)br- Carolina Horse Park Foundation (12.7 miles)br- The list goes on and on... brbrEV Charging is available just a short walk (0.2 miles) from the property at the Southern Pines Library. brbrThe Shire 255 is managed by Stay Well Vacation Rentals, a locally owned company offering a personalized experience and deep knowledge of the area. We live and work right here in Moore County and love interacting with our guests. As local Realtors, we`re happy to offer insights or recommendations about the area. Feel free to reach out anytime – we`re just a message away!brOut of respect for other guests and due to shared walls in The Shire 255, pets are not allowed. Any unauthorized pets will incur a $250 fee. Please check Unit D, a detached cottage, availability for all reservations with pets including service animals.

Sienna at The Shire 255 - Unit B - Downtown!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(8)

$169.99

Location, Location, Location! In the heart of Downtown, steps from the shops and restaurants, Sage at The Shire 255 is the perfect retreat for couples or traveling professionals looking to be in a lively and walkable area. When we say walking distance from downtown, we mean it! You will be a short distance from a number of wonderful dining options, breweries, wine shops and boutiques. Below are a few of our favorite local spots worth checking out. brbrLocated at the front of the main residence, this quaint unit makes for the perfect getaway. The Sage Cottage features a Queen Bed and Full Size Sleeper Sofa, to accommodate up to four guests. This unit has an efficiency kitchen with full size refridgerator, two-burner stove, microwave, and toaster oven, as well as an in-unit washer and dryer. Our property is pet-friendly with pet fee. We kindly ask that pets stay off furniture out of respect for future guests! brbrWe offer discounts for weekly and monthly stays. Reach out directly to inquire. brbrPlan ahead and book the entire Shire retreat, made up of three luxury spaces, this property can sleep up to 10 guests. Add privacy and comfort to any family vacation or work trip. brbr- 400` to The Jefferson Inn (live music on the weekends)br- 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) br- 0.2 miles to Ashtens br- 0.2 miles to The Bell Tree Tavern br- 0.3 miles to Southern Pines Growler br- 0.3 miles to So Pines Pizza br- 0.4 miles to Southern Prime Steakhouse (fancy dinner) br- 0.6 miles to Betsy`s Crepes (the best breakfast spot around, in our humble opinion) br- 0.8 miles to Sly Fox (the butter chicken dish is to die for - don`t take my word for it)br- Carolina Horse Park Foundation (12.6 miles)br- The list goes on and on... brbrEV Charging is available just a short walk (0.2 miles) from the property at the Southern Pines Library. brbrThe Shire 255 is managed by Stay Well Vacation Rentals, a locally owned company offering a personalized experience and deep knowledge of the area. We live and work right here in Moore County and love interacting with our guests. As local Realtors, we`re happy to offer insights or recommendations about the area. Feel free to reach out anytime – we`re just a message away!brOut of respect for other guests and due to shared walls in The Shire 255, pets are not allowed. Any unauthorized pets will incur a $250 fee. Please check Unit D, a detached cottage, availability for all reservations with pets including service animals.

Sage at The Shire 255 - Unit A - Downtown!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(61)

$165.5

This beautifully upgraded condo offers the perfect blend of privacy, luxury, and location, making it the best choice for your Pinehurst stay. Tucked away at the far end of the development, this end-unit condo provides peace and quiet while still being close to everything.brbrUpgrades include plantation shutters throughout, Brazilian cherry hardwood flooring, granite countertops, stainless steel appliances, and all-new windows. The open-concept kitchen and living room feature cathedral ceilings, a cozy fireplace, and abundant natural light.brbrThe spacious master suite includes a jacuzzi tub and shower, while the guest bedroom offers a private bathroom for added comfort. Step outside to the private brick patio and enjoy stunning golf-front views.brbrAdditional amenities include a washer and dryer and a K-Cup coffee machine in the kitchen. Please note that steps are required to access the front door, and there are two assigned parking spots in front of the unit. brbrBook your stay today and experience Pinehurst in style and comfort!brPrimary Bedroom - 1 King bedbrBedroom 2 - 2 Full bedsbrbrGrill at unit is not for guest use. brbrFor insurance and security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. brBy completing the reservation you understand that your check-in instructions might be withheld until you have successfully completed our verification portal.

Condo

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

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$69.55

The Knollwood Inn is an attached private entrance apartment located in the prestigious Knollwood Heights community. The apartment is located in the heart of Southern Pines, less than .5 miles to the sought-after Pine Needles Golf Course and less than 1 miles to Downtown Southern Pines. The Knollwood Inn is has a completely private entrance on the right side on the main house with its own parking space.

The Knollwood Inn located less than .5 miles from Pine Needles Golf Course!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(21)

$212.44

This downtown Southern Pines cottage is just 1 mile from SoPines shops, restaurants, bars & theatre. Relax & unwind in this stylish & cozy 3 bedroom cottage with a King bed in the master bedroom, Queen bed in the 2nd room and 2 twin beds in the 3rd. Each room comes with a 32inch smart TV, bedside lamps, alarm clocks & white noise machine with multiple USB chargers allowing you to get a worry-free, peaceful sleep. Kitchen is well stocked with a full Coffee bar, Washer & Dryer off the kitchen stocked with laundry essentials for your entire. The living room has a Smart TV, cabinet full of games and a peaceful view of the pines in the fully fenced front yard. Relax after a long day on the back deck while playing cornhole, putting games or sitting around the fire pit (firewood supplied) and cooking on the Blackstone grill ( grilling utensils supplied) keep robot & upright vacuum at the home at all times along with cleaning supplies and bathroom necessities for use during your entire stay. This home is perfect for whatever reason brings you to the pines. Whether it's golf, military, family or passing through. Just 3.5 miles to Longleaf Country Club home to US Kids Golf. 1/2 mile to Pine Needles golf club & Mid Pines golf club and 8 miles to Pinehurst Resort! 14 miles to Carolina Horse park, 30 Minutes to Ft Bragg & 1 hour to RDU Airport

Midland Pines Getaway! 3 bedroom stylish & cozy Cottage minutes to golf & dining

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(31)

$375.32

The perfect spot to relax & golf- MIDWAY to all Pinehurst/Southern Pines offer!brbrAfter spending a day on one of 25 courses within 5 miles (less than a mile to Mid Pines & Pine Needles), you will it a hole in one whether you hit the town (minutes from Pinehurst Village & downtown Southern Pines) or stay in to grill out, play cornhole & unwind with a drink by the fire pit & a game of pool.brbrAlso a fantastic place for a girls' weekend, or family retreat! 30 minutes to Fort Liberty.

Fire Pit- Pool Table- 8 Beds- Midway House

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(35)

$168.74

Welcome to the Oakmont Cottage! Located in the heart of Southern Pines. Just a short walk from the historic downtown, with shops, restaurants & nightlife. Only minutes away from the area's best courses: Southern Pines (5 min) , Mid Pines (5 min), Talamore (6 min), Mid-South (8 min), Pine Needles (8 min), and Pinehurst Resort (11 min). Utilize our exclusive Golf Booking Concierge for advance tee times at over 13 area courses. The perfect space for your next golf trip or southern getaway!brbrSleeps up to eight guests: Master bedroom (King Bed), second bedroom (Queen Bed), third bedroom (Two Full Beds) and a sleeper sofa. Large living room with two couches and a TV. Two full bathrooms for plenty of space to get ready for golf. Full kitchen, fully stocked and spacious dining area. Kick back and relax on the front porch or enjoy yourself well into the evening around the backyard fire pit!

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

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(7)

$199.12

Unbeatable Location! In the heart of downtown, The Shire 225 is the perfect retreat for families or traveling professionals looking to be in a lively and walkable area. Our multi-family property consists of four private units situated under the pines. Originally built in the 1900`s, the home has been lovingly renovated by its current owners. We welcome you to experience what life in Southern Pines is all about. brbrUnit C, nicknamed `Slate`, is a two-bedroom, one-bathroom apartment located on the back of the main residence and accessible by a flight of stairs. brbrThe two bedrooms, one with a queen bed and the other with a king, are thoughtfully designed for relaxation, complete with plush bedding, sound machines, ample hangers and luggage racks for ease of traveling. The desk in the second bedroom is perfectly set up for remote work, with a comfortable chair, ample lighting, and a quiet, focused atmosphere.brbrListing Access: We utilize an electronic keypad for access and the code will be sent to you prior to arrival. brbrListing Interaction: We live and work in the area and are always happy to provide tailored recommendations. Please feel free to reach out. We are just a message away. brbrNeighborhood Overview: brDowntown Southern Pines is full of many restaurants and boutiques for exploring. You are sure to love the convenience of being a few steps from it all. When we say close to it all, we mean it! brbrHere are a few of our favorite local spots within walking distance from the property: br- 400` to The Jefferson Inn and Bar (live music on the weekends)br- 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) br- 0.2 miles to Ashten`s br- 0.2 miles to The Bell Tree Tavern br- 0.3 miles to Southern Pines Growler br- 0.3 miles to So Pines Pizza br- 0.4 miles to Southern Prime Steakhouse (upscale dining) br- 0.6 miles to Betsy`s Crepes (the best breakfast spot around, in our humble opinion) br- 0.8 miles to Sly Fox (the butter chicken dish is to die for - but don`t take our word for it)br-Carolina Horse Park Foundation (12.6 miles)br- The list goes on and on... We live and work in Southern Pines so please reach out if you`re looking for tailored recommendations.brbrThe Shire 255 is managed by Stay Well Vacation Rentals, a locally owned company offering a personalized experience and deep knowledge of the area. We live and work right here in Moore County and love interacting with our guests. As local Realtors, we`re happy to offer insights or recommendations about the area. Feel free to reach out anytime – we`re just a message away!brOut of respect for other guests and due to shared walls in The Shire 255, pets are not allowed. Any unauthorized pets will incur a $250 fee. Please check Unit D, a detached cottage, availability for all reservations with pets including service animals.

Slate at The Shire 255 - Unit C - Downtown!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(26)

$617.74

Many have called Southern Pines Retreat home throughout its nearly 100 year history. Built in 1928, this Georgian-style home will offer you, your family, your friends, and your furry companions an opportunity to experience the historic charm of Southern Pines and the surrounding areas. The home is located conveniently on the west end of downtown Southern Pines, walkable to all of the dining, shopping, and recreation that Broad Street has to offer, including:brbrRed's Corner outdoor bar and food truck plaza - 1/4 milebrRec Room Arcade Bar - 1/4 milebrHatchet Brewing Company - 1/2 milebrNewly-Renovated Southern Pines Golf Club - 1/2 milebrHeart of Downtown Southern Pines - 3/4 milebrbrThe Southern Pines Retreat is a 4 Bedroom, 3.5 Bathroom home set in a quaint residential area of Southern Pines. Some of the oldest and largest longleaf pines and magnolia trees in the area are here in the yard for you to admire.brbrOur favorite aspects of The Southern Pines Retreat:brbr- The fully-fenced in backyard with covered dining, grill, and hot tubbrbr- The old style architecture of the home truly makes you feel like you're stepping back in time!brbr- The laundry room with built-in dog wash station is a perfect home away from home for your furry friends.brbr- Open concept kitchen and dining areas allow the conversation to flow freely between spacesbrbrHere are just some of the unique features of this stunning property:brbr- Backyard with room to play, cook, eat, and relaxbrbr- Large deck in the backyard overlooking a small grassy area and the hot tubbrbr- Updated master bathroombrbr- Spacious living room with vintage fireplace and mantlebrbr- Six (6) total beds:br2 King, 1 Queen, 1 full, 2 twinbrbr- Spectrum Internet with wi-fi throughout the home and Spectrum streaming on all TVsbrbr- Large 6-seat hot tubbrbr- Large driveway with room for several vehiclesbrbrWe offer laundry detergent, a fully stocked kitchen including cookware, spices and pantry items, hand soap, shampoo/conditioner, body wash and toilet paper and paper towels to get you started.brbrWe do not allow events or parties of any kind. We have a strict maximum of 10 guests. Please, under no circumstances, can there be more than 10 guests in the home at a time.brbrWe will consider your 4 legged canine family members on a case-by-case basis and a $200 pet fee. Please tell us about your pup. We will consider up to 2 dogs and kindly ask that no dogs be allowed in or on any of the furniture and kenneled/crated if left home alone. Please note - we can not accept your feline family members as guests at this time. No cats allowed in the home.brbrSleeping Accommodations:brbrMaster Bedroom (upstairs): 1 King Bed with large private full bath, including dual vanities, a walk in shower and soaking tubbrbrBedroom #2 (upstairs): 1 King Bed, shared full bath in hallwaybrbrBedroom #3 (upstairs): 2 Twin Beds (trundle) and 1 Full Bed, shared full bath in hallwaybrbrBedroom #4 (main level) - private suite with Queen bed and full bathbrbrbrEarly Check-in and/or late Check-Out may be arranged for additional $100 fees each (subject to availability).

Historic Home w/hot tub, steps from everything!

Southern Pines, North Carolina, United States

Bed

Sleeps

$417.99