Vacation Home Rentals By Owner In Southern Pines, NC

Steps from shopping and dining! This beautifully updated Downtown home stands out with its high end finishes and unique location. Located Downtown Southern Pines, this home offers a fantastic opportunity for those craving walkability. Quaint coffee shops, trendy breweries, and delectable dining options are at your fingertips. After you`ve explored downtown, come home and relax on the spacious back deck with a cold drink and enjoy the peaceful surroundings. Featuring high end finishes and stylish, modern décor, this house is the perfect place to enjoy your time in the land of the pines!brbrEarly check-in subjected to availability with an additional fee: brUp to 2 hours for $50brUp to 4 Hours for $80brbrUnauthorized pets will incur an additional pet fee.brbrNearby Attractions:brbr- Carolina Horse Park Foundation (13.8 miles)brbrAt Stay Well Vacation Rentals, we are experts in prioritizing the guest experience through unparalleled customer service. We are a locally owned management company and take your vacations seriously. We appreciate how expensive it can be to travel, not only financially but also in cost of vacation days. We want to ensure you have the best vacation possible and we are dedicated to delivering that experience to each guest.brEnjoy this space, we have curated the perfect space for a family getaway. brbrNo cats permitted on property, unauthorized pets will incur additional fees. EV charging available for $20/day.

The Flat Coat Cottage: Downtown Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$696.87

4.5 Acres | Private Pool | Game Room | Dog Friendly w/ FeebrbrYour next fun-filled North Carolina adventure awaits at this secluded Southern Pines vacation rental! With a private pool, fenced-in yard, and prime location surrounded by serene nature trails, world-class golfing, and more, this 4-bedroom, 4.5-bath house makes the perfect destination for a memorable retreat with family or friends. Be sure to check out downtown shops and eateries before returning home to unwind by the fire pit.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3: 2 twin bedsbr- Bedroom 4: 1 queen bedbrbrINDOOR LIVINGbr- Smart TVs w/ cablebr- Theater room w/ projector screenbr- Luxury massage chairbr- Pool table, dartboardbr- Fireplace, dining table br- En-suite bathrooms, walk-in closetbr- Walk-in shower, freestanding bathtubbrbrOUTDOOR LIVINGbr- Private pool w/ waterslide, hot tubbr- Wood-burning fire pitbr- Putting greenbr- Furnished patio & pergolabr- Fenced-in yard w/ hammockbrbrKITCHENbr- Refrigerator, stove/oven, microwave, dishwasherbr- Drip coffee maker, toasterbr- Island w/ bar seating, dishware & flatware, cooking basicsbrbrGENERALbr- Self check-in, free WiFibr- Washer & dryer, laundry detergentbr- Iron/board, trash bags/paper towelsbr- Towels/linens, complimentary toiletries, hair dryerbr- Central heating & A/C, ceiling fansbrbrFAQbr- 1 exterior security camera (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-level house, 2 steps required to enterbr- All bedrooms & full bathrooms on main floorbrbrPARKINGbr- Driveway (8 vehicles)brbr-- THE LOCATION --brbr- Near golf courses & hikingbr- 1 mile to Weymouth Woods Sandhills Nature Preservebr- 3 miles to Downtown Southern Pines: restaurants & cafes, shopsbr- 3 miles to Southern Pines Golf Clubbr- 6 miles to Mid Pines Inn & Golf Clubbr- 6 miles to Pine Needles Resortbr- 7 miles to Reservoir Park: fishing, trails, disc golfbr- 8 miles to Pinehurst Resortbr- 72 miles to Raleigh-Durham Int’l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $300 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-level house requires using 2 steps to enter. Upon entry, all of the bedrooms and full bathrooms are accessible on the main floorbr- Your safety matters. This property features 1 exterior security camera located on the back patio facing the outdoor entry. It does not look into any interior spaces. The camera records video and sound when activated by motion

Fire Pit + Patio: Spacious Southern Pines Retreat

Southern Pines, North Carolina, United States

Bed

Bath

8

Sleeps

$805.75

The Lodge at Twin Fields Farm | Luxury Historic Barn StaybrbrExperience an unforgettable stay at The Lodge at Twin Fields Farm, a beautifully renovated historic barn listed on the National Register of Historic Places. Blending refined luxury with authentic countryside charm, this one-of-a-kind lodge is ideal for golf getaways, bachelor weekends, hunting trips, and group retreats.brbrThe lodge features three distinct luxury suites:brbrThe Foxhound Suite – Four single beds, kitchenette, and private en-suite bathroombrbrThe Thoroughbred Suite – Four single beds, kitchenette, and private en-suite bathroombrbrThe Albatross Suite – An exclusive king suite with a private en-suite bathroombrbrDesigned for comfort and flexibility, the property offers two state-of-the-art, fully equipped kitchens, perfect for group meals or entertaining. Original barn stalls have been thoughtfully preserved, adding character and delivering an authentic farm-stay atmosphere without sacrificing modern amenities.brbrWhen you book The Lodge at Twin Fields Farm, you’ll enjoy exclusive access to the entire building—both floors of this spacious historic barn. Guests have access to five bedrooms, multiple living spaces, and two full kitchens, ensuring privacy, convenience, and room to relax.brbrEquestrian-Friendly StaybrTwin Fields Farm welcomes guests traveling with horses. Advance inquiry is required, as availability is limited. The property is within walking distance of the Walthour-Moss Foundation, making it an ideal location for equestrian enthusiasts.brbrWhether you’re planning a weekend escape or a memorable group stay, The Lodge at Twin Fields Farm offers a rare combination of history, luxury, and countryside charm.

Golf & Hunting Retreat - Luxury Historic Barn Near Pinehurst

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$421.07

Welcome to The Cowboy, hosted by Isle of the Pines Property Group – a striking home seamlessly blending modern-western decor in a prime location near downtown Southern Pines. This thoughtfully designed home offers a unique atmosphere, embodying a luxury cowboy vibe!brbrWe pride ourselves on the inviting space we provide through offering luxury amenities such as a fully equipped kitchen, abundantly stocked coffee bar, toiletries upon arrival, several family oriented games, and so much more!

The Cowboy

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$179.65

This SMOKE-FREE property is an excellent 3BR 2BA base camp for anyone golfing, working, or traveling in the Southern Pines or Pinehurst area. The master suite is immaculate as are the two full bathrooms, with modern fixtures and a clean, bright ambiance. Enjoy a dining room illuminated by evening sunlight. Walk across the original pine floors and find a well-appointed kitchen. Take a pause in the sunny breakfast room surrounded by walls of windows: the perfect place to work, gather, or just reset. brbrDid we mention golf Take a look at our proximity to these great courses:br· 4 minutes (1.3 miles) to Pine Needles Golf Clubbr· 4 minutes (2.0 miles) to Mid Pines Inn & Golf Clubbr· 5 minutes (2.3 miles) to Talamore Golf Resortbr· 5 minutes (2.8 miles) to Longleaf Golf & Family Clubbr· 7 minutes (4.4 miles) to Hyland Golf Clubbr· 8 minutes (4.1 miles) to Pinehurst No. 9br· 9 minutes (4.0 miles) to Forest Creek Golf Clubbr· 9 minutes (4.7 miles) to Southern Pines Golf Clubbr· 10 minutes (5.0 miles) to The Country Club of N.C.br· 11 minutes (5.4 miles) to Pinehurst No. 2

Convenient Cottage in the Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$461.04

House is located on Pine Needles golf course hole #16. Enjoy coffee & cocktails on the enclosed porch or deck while watching golfers play the par 3. brThis 4 King Bedroom (each with TVs) 2 Bath is perfect for golf foursomes, equestrian or visiting families. Enjoy a game of pool or poker and evenings around the gas fire pit. brPlay golf at over 40 courses in the Sandhills. br7 minutes to the charming downtown of Southern Pines and 10 minutes to Pinehurst for boutique shopping and a buzzing dining district. The reservoir for hiking and water activities is 2 minutes away.

Golf Front home on Pine Needles. 4 King Beds : 5 miles from villages

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$259.16

Elevate your next visit to North Carolina by staying in this newly constructed 3-bedroom, 2.5-bathroom Southern Pines townhouse. Boasting 1,600 square feet of luxurious living space, this vacation rental home is just steps away from boutique shops and fine dining restaurants along Broad Street. Spend your days strolling around the quaint town, enjoying some tee time, or unwinding on the private deck in the backyard and enjoying a relaxing day outdoors.brbr-- THE PROPERTY --brbr200 Mbps Fiber-Optic WiFi | 2 Smart TVs w/ Roku | Remote Work FriendlybrbrThis well-appointed home offers a stress-free getaway for families and friends. Enjoy 200 Mbps fiber internet and Rokus in the living room and bedroom suite for an easy transition from work to play. It's the perfect spot to stream your favorite apps and relax in a convenient location!brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Additional Sleeping: Queen-Sized Beauty rest Air MattressbrbrINDOOR LIVING: Open-concept living area, modern decor & furnishings, 2 flat-screen TVs, PlayStation 4, en-suite bathroomsbrOUTDOORS: Spacious deck w/ outdoor dining table, forest viewsbrKITCHEN: Fully equipped, stainless steel appliances, granite countertops, wood table w/ seating for 6, kitchen island, Keurig coffee maker, blender, knife set, 2 Smart TVs w/ Roku (upstairs bedroom suite & living room)brGENERAL: Linens/towels, washer/dryer, complimentary toiletries, suitable for children & elderly, ceiling fans, central heat, hair dryer, doorbell camera (facing out), 200 Mbps fiber-optic WiFibrPARKING: Garage (2 vehicles), driveway (1 vehicle)brbr-- THE LOCATION --brbrTHINGS TO SEE & DO: Sunrise Theater (1.1 miles), Reservoir Park (4.8 miles), Sandhill Horticultural Gardens (5.8 miles), The Splash Pad (6.7 miles), Black Rock Winery (11.2 miles), Rockingham Speedway (20.0 miles), Aloha Safari Zoo (26.2 miles), Uwharrie National Forest (32.6 miles), Morrow Mountain State Park (55.4 miles)brGOLF COURSES: Southern Pines Golf Club (1.1 miles), Pine Needles Golf Course (2.9 miles), Talamore Golf Course (2.9 miles), Hyland Golf Club (4.7 miles), Pinehurst Resort Golf Course (5.6 miles)brBREWERIES: Hatchet Brewing Company (0.3 miles), Southern Pines Brewing Company (2.3 miles), Railhouse Brewery (3.9 miles), Pinehurst Brewing Company (6.3 miles)brAIRPORTS: Fayetteville Regional Airport (39.5 miles), Raleigh-Durham International Airport (69.9 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Must be at least 21 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed

Downtown Townhome; Walk to Dine & Shop on Broad St

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$474.04

Walkable to Downtown! Stay comfortably in Southern Pines at this 4-bedroom house on Illinois Street. Each bedroom features a queen bed for a good night's sleep. Enjoy the beautiful living room with 2 sofa beds for extra guests. With 3 bathrooms equipped with a bathtub and shower, getting ready is a breeze. This gorgeous property also offers amenities like AC, WiFi, and a fitness room. Make your holiday one for the books with a stay at our place.

Blue Beauty

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$445.28

The 19th Hole is a 4 bed, 3.5 bath home located near the heart of downtown Southern Pines. Enjoy the convenience of being within walking distance to restaurants, pubs, & shops, while also being steps away from a beautiful park featuring a playground & pickleball courts!brbrThe property features tastefully sourced furnishings and decor that is designed to create a relaxing contemporary aesthetic that can be enjoyed by guests of all ages.brbrThis home is designed to bring people together in the large open common spaces, while giving each guest privacy when needed. The house can comfortably sleep 12.brbrEven the most discerning of chefs will fall in love with the large kitchen, with high-end stainless steel appliances, where any meal can be prepared for the entire group.brbrThe property offers a fenced in backyard, including Adirondack chairs with a propane firepit, dining table and grill for cooking where you can kick back and relax after a long day.brbrRight next to our property, you’ll find a fantastic public park that’s completely free for our guests to enjoy. The park features a variety of amenities, including: Modern playground equipment for kids, Pickleball courts, Volleyball court, Basketball court, Tennis courts and much more.brbrEven better — we provide sports equipment for your use, so you can jump right into the fun without bringing your own gear! It’s the perfect spot for outdoor fun and a bit of friendly competition—just steps from your stay.brbr-----------------------------------------------------------------brbrMore about the bedrooms:brbrBedroom #1 (Queen Room) - Sleeps 4br2nd floor. Includes 2 Queen beds (Nectar Premier Hybrid 13 Mattress), 3 nightstands, bedside lamps with USB ports, closet, black-out cellular shades and a private office. Shared hallway bathroom.brbrBedroom #2 - Sleeps 2br2nd floor. Includes King bed (Nectar Premier Hybrid 13 Mattress), 2x nightstands, bedside lamps with USB ports, smart TV, closet, black-out cellular shades and a private office. Shared hallway bathroom.brbrBedroom #3 (Master Suite) - Sleeps 2 br1st floor. Includes King bed (Nectar Premier Hybrid 13 Mattress), 2x nightstands, bedside lamps with USB ports, smart TV, attached private master-suite with shower, duel vanities, walk-in closet, and black-out cellular shades.brbrBedroom #4 (Master Suite) - Sleeps 4 br2nd floor. Includes King bed (Nectar Premier Hybrid 13 Mattress), 2x nightstands, bedside lamps with USB ports, smart TV, dresser, and bunk beds (children preferred; top bunk max weight 200lbs). Includes attached private master-suite, with shower/tub, and black-out cellular shades.brbrGuests will have full access to all 4 bedrooms, 3.5 bathrooms, the open concept kitchen/living room, loft area and outdoor patio space.brbrWe also provide the following items for your stay:brbr- Wifi internet access is provided (via Spectrum speeds up to 1 Gig)br- 5x smart TVsbr- Bluetooth Record Playerbr- Pack 'n' Play, high chair & baby monitorbr- Hair dryers br- Sound machines in each bedroombr- Shampoo, conditioner, and body wash in each bathroombr- Other common toiletries in case you forgot somethingbr- Multiple smoke/carbon monoxide detectorsbr- Fire extinguishersbr- First-aid kitsbr- Each bed includes cotton sheets, pillows, a comforter, foldable luggage storage racks plus extra blankets and pillowsbr- Ceiling fans in each bedroom, plus portable desk fans for usebr- Crock pot, blender, Insta Pot, popcorn maker, hand mixerbr- Electric tea kettle - teas and honey sticks to get you startedbr- Toasterbr- 12 cup coffee maker - coffee & creamers to get you startedbr- Iron / iron board & portable steamerbr- Ample plates, bowls, glasses, coffee mugs, and silverware for all guestsbr- Various Baking Sheets, serving platters, and bowlsbr- Plastic dinnerware & drinkware for kidsbr- Cooking spices, foil and Tupperware for cookingbr- Wine bottle openerbr- Heating pad & touchless thermometer br- Plenty of towels for all guests br- Various board gamesbr- Washer/Dryer for clothesbr- Sports equipment to use for amenities at Memorial Parkbrbrbr-----------------------------------------------------------------brbrWhy you should consider staying with us:brbr1. We love our home - We are not just home-owners trying to offset our mortgage costs with the occasional short-term guest. We personally use our home often and treat our guests as if we were staying there. We strive to create an exceptional and memorable experience with each and every stay.brbr2. We believe communication is key -- From your initial booking request, through the day you check-out, we are available to answer any and all questions or concerns. We also provide detailed documentation needed to access the property, including driving directions, access codes, and an on-site welcome guide.brbr3. We Self and Co-Host -- This means you wont be speaking with some property management company staffer who has never stayed at the home, and who may not be familiar with the Southern Pines area.brbr4. Amenities -- We go above and beyond to provide many extra kitchen and bath accessories as we want to make sure that you have what you need to enjoy your stay. brbr5. Beds -- We believe that a poor night's sleep can really undercut one's vacation. That is why we invest in high-quality mattresses, pillows, and sheets for each and every room. All of our mattresses are brand new as of 2024.brbr6. Furnishings and Decor -- Our property has been carefully designed to create a feel that is functional, inviting, and enjoyable for guests of all ages.brbrDepending on traffic, our home is 1hr 10min drive from Raleigh-Durham International Airport.brbrAs stated our house is directly next to Memorial Park.brFree admission to:brBallfield - LightedbrBaseball / SoftballbrBasketball Court - Outdoor, LightedbrBocce Ball CourtbrFootball FieldbrGreenspace / Open Play AreabrHorseshoesbrPickleball Court - Outdoor, LightedbrPicnic TablesbrPicnic Tables with Grills - OutdoorbrPlayground EquipmentbrRacquetball Courts - Outdoor, LightedbrRestroomsbrShuffleboard CourtsbrTennis Courts - Outdoor, LightedbrVolleyball Court - Outdoor, Sandbr brRestaurants/pubs within walking distance:brBeefeaters 0.3mbrSpice Cafe 0.3mbr715 Bar & Grill 0.4mbrThe Sly Fox Pub 0.4mbrHatchet Brewing Company 0.4mbrRec Room Bar and Arcade 0.4mbrJava Bean Roasting Company 0.4mbrRed's Corner 0.5mbrPony Espresso 0.5mbrTaqueria La Mexicana 0.5mbrVito's Ristorante & Pizzeria 0.5mbrScott's Table 0.5mbrSouthern Pines Growler 0.5mbrSouthern Prime Steakhouse 0.6mbrbrWalkable Spas:brRevive Spa & Lash Lounge 0.3mbrVenus Skincare Spa 0.5mbrBody Harmony Southern Pines 0.6mbrbrDrive to these local golf courses:brSouthern Pines Golf Club 1.1mbrMid Pines Inn and Golf Club 2.4mbrPine Needles Lodge & Golf Club 2.5mbrKnollwood Fairways & Driving 2.4mbrTalamore Golf Course 2.9mbrLongleaf Golf & Family Club 3.4mbrPinehurst Golf Courses between 4-8mbrbrGrocery stores:brNature's Own Market 0.7mbrLowes Foods of Southern Pines 1.3mbrFood Lion 1.8mbrWalmart Supercenter 2.3mbrbrNOTE: if you are shipping items to the house, only UPS and FedEx will be able to complete the delivery. Do not ship items via USPS to the house.

19th Hole - Pickelball, Park, Walk to Downtown

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$367.25

Welcome to The Velvet Pine: our Cozy 3 Bedroom Rancher [with additional Queen pullout sleeper], and 2 Full Baths. We are snuggled in a quiet neighborhood adjacent to downtown southern pines. Restaurants, shops, ice cream, breweries, and more are a 3-minute drive or 15-minute walk away! (cross Indiana Ave and turn left). Our home is stocked with amenities to help make your stay convenient and memorable. Such as a fully stocked kitchen, coffee station, comfortable beds, basic soaps and shampoos, hair dryer, toilet paper and fresh towels in the bathrooms, fresh linens on beds. (extras in the hall closet) We also have a pull-down ironing board & iron next to the washer and dryer, wireless internet, Roku TV, central heating and air, a fitness room, and a furnished back deck with a private woodsy view. We hope you have a wonderful time as our guest and get to fully enjoy everything our beautiful town has to offer!

The Velvet Pine_ Cozy Rancher_Entire Home_3 minutes from Downtown Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$226.13

Experience the perfect blend of historic charm and modern comfort in our restored 1920s Serenity Pines cottage, nestled in the heart of Southern Pines. This charming home combines its original character with tasteful modern touches, including plush linens, towels, and extra amenities. Enjoy the convenience of being just 3 blocks from downtown's restaurants, shops, and breweries. Unwind on our spacious deck or stroll through the picturesque neighborhood. Whether you're in town for golfing, riding, or simply soaking up the southern charm, Serenity Pines cottage has everything you need for a dream stay. Come and indulge in its warmth for yourself!

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

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$302.14

Location! Steps from Downtown Southern Pines! This charming property is situated in the heart of Downtown Southern Pines, allowing you the convenience of being steps away from many coffee shops, vibrant restaurants, and a variety of unique shops. Whether you`re coming to town for work, to visit family or friends, you will feel right at home at Maine Avenue. brbrStay Well Vacation Rentals is proudly locally owned, offering a personalized experience and a 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!brbr★ LIVING ROOM ★brEnjoy a peaceful evening at home, nestled in a cozy, comforting space.brbr- Comfortable Sofa with Pillows & Blankets br- Additional Seating for Extra Comfort br- Smart TV With Netflix, Hulu, Amazon Downloaded!br- Large Windowsbr- Stylish Decor brbr★ KITCHEN ★brFully equipped kitchen for an easy choice between dining in or eating out!br br- Refridgerator br- Microwave br- Stovebr- Ovenbr- Drip Coffee Machinebr- Coffee Groundsbr- To-go Coffee Cupsbr- Wine Glasses br- Dishes & Silverwarebr- Large Sinkbrbr★ DINING AREA ★brEnjoy being together, sit over the table for a board game or a nice meal as you laugh and compare your favorite memories from your stay. brbr- Quaint Circular Dining Table br- Seating For 4 Guestsbr- Table Mats brbrbr★ BEDROOMS ★brEach bedroom has been curated to ensure that your stay is filled with comfort. brbr- Luggage Racks br- Pristine Linen and Blanketsbr- Throw Blankets and Pillowsbr- Additional Storage br- Stylish Decorbr- Night Stands With Lampsbrbr☆ SLEEPING ARRANGEMENTS - 3 BEDROOMS ☆brMaster Bedroom: Queen BedbrBedroom 2: Queen BedbrBedroom 3: Queen BedbrbrEnjoy the convenience of seamlessly blending work and play, with a dedicated desk and chair in Guest Bedroom #1.brbr★ BATHROOM ★brStocked with all of your essential needs, you will be able to pack light for your upcoming stay!brbr- Showerbr- Bathtub br- Vanitybr- Mirrorbr- Toiletbr- Towelsbr- Hair Dryerbr- Essential Toiletriesbr- Soaps & Suds Provided brbr★ OUTDOOR AREA ★brEnjoy the seclusion of your own private oasis right outside of the living roombr- Fenced Yard br- Seating For 4 On The Patiobrbr★ LOCAL FEATURES ★br- Walkable Local Favorites: br ⋆ Ashtens - A fine dining experiencebr ⋆ Swank Coffee Shoppe - Known for their coffee, baked goods and local treasures!br- The Ice Cream Parlor: 0.4 Miles br- Rec Room Bar & Arcade: 1.3 Milsbr-Carolina Horse Park Foundation (13.8 miles)brbrWe are here to ensure you have a comfortable and enjoyable stay! Feel free to reach out to me anytime if you need assistance, recommendations, or have any questions during your visit. We respect your privacy, but we`ll be happy to help in any way I can to make your stay memorable. Safe travels, and we look forward to hosting you! Book your stay today and immerse yourself in the charm of Southern Pines with Stay Well!brbrAt Stay Well Vacation Rentals, we are experts in prioritizing the guest experience through unparalleled customer service. We are a locally owned management company and take your vacations seriously. We appreciate how expensive it can be to travel, not only financially but also in cost of vacation days. We want to ensure you have the best vacation possible and we are dedicated to delivering that experience to each guest.brEnjoy this space, we have curated the perfect space for a family getaway. brbrNo cats permitted on property, unauthorized pets will incur additional fees. EV charging available for $20/day.

Entire Home - Walkable to Downtown Southern Pines - Local Gem

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$521.49

Welcome to Lazy Afternoon in the Pines! We are nestled in a family friendly neighborhood in Moore County. Our location can't be beat. We are just a 5 minute drive from Downtown Southern Pines, 15 minutes from Pinehurst, and 25 minutes from Ft. Bragg. Access the Home of American Golf from this spacious 5 bedroom 2.5 bath home. For the non-golfer, the home is equipped with every amenity you would expect from your own home plus Ping-Pong, darts, swimming pool, and local hiking trails. brbrSEASON UPDATESbrbrSpring is coming. One of our favorite times of year! With spring comes the pollen. Please note we try our best to maintain the outdoor space put the pollen is a force of nature.brbrTHE SPACE brbrPreviously our family home, we spent the better part of 3 years updating this house before being moved (again) by the military. We have the space for everyone to have privacy but you are all going to want to spend your time together in the new kitchen, game room, or in the pool. We hope this feels like home to you too! brbrLIVING SPACES brbrAs you pull up to Lazy Afternoon you will notice the long driveway that can accommodate up to 4 vehicles. The front door opens to a large dining room and large living room with all new furnishings. The open concept kitchen and living room allows for you to host several people without feeling to confined. Kick back with your drink of choice and watch your favorite sporting event or movie on the large Smart TV or just cozy up to the gas fireplace on the couch. The garage is just off the kitchen and is home to our Ping-Pong table. brbrCOOKING AND DINING brbrThe kitchen is the hub and central to everything on the main level. The big bay window looks out to the back deck and private pool. Prepare snacks for the kids after pool time or get dinner ready in this fully equipped kitchen. All stainless appliances and InstaPot make meal prep and planning a breeze. brbrBEDROOMS AND BATHROOMS brbrThe primary bedroom suite is the only bedroom on the main level. Just off the kitchen, this master bedroom is going to be the one you want! King bed, dual nightstands, large walk-in closet, and master bathroom with heated floors and a giant shower. brbrThe remaining 4 guests bedrooms are just upstairs. 2 rooms have queen beds and 2 rooms have king beds. All king bedrooms have wall mounted Smart TVs. All Bedrooms have nightstands with USB and power plugins. The upstairs has 1 full bath with tub/shower, and dual vanity. brbrOUTDOOR AMENITIES brbrIf you are here in the warmer months, the pool and the expansive backyard are going to be the star of the show. Be the judge of the kids cannon ball contest from our pool house bar or watch the game on the Smart TV at the pool house deck. During halftime play some darts in the pool house! Our July guests can check to see if the fruit is ripe on our 2 backyard peach trees. There is comfortable outdoor seating for all on the deck with outdoor BBQ.brbrCHECK-IN / CHECK-OUT brbr• Check-in Time: 4:00 PM br• Check-Out Time: 10:00 AM brbrNote: We don't pre-approve early check-in or late check-out. If the property is ready prior to 4 PM on your check-in date, we'll notify you of the early access. Due to our very tight cleaning schedule, we don't offer late check-outs. If you need additional time, please consider adding an additional night to your reservation. brbrNo Check-in or Check-out on the following holidays: brbr⌀ Easter Sunday br⌀ July 4th br⌀ Thanksgiving Day br⌀ Christmas Day br⌀ New Year's Day brbrCANCELLATION POLICY & TRIP INSURANCE brbrWe encourage all guests to purchase travel insurance to cover any unforeseen circumstances that will affect their trip. No refunds will be given due to weather, natural disasters, travel delays, or cancellations. No exceptions will be made to the cancellation policy in place at the time of booking. brbrWe have partnered with RentalGuardian to give our guests easy access to travel insurance choices when they book with us. We do not sell travel insurance nor receive a commission; this is fully for the benefit of our guests.

This is it! | Pool | Golf | Convenient to Town

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$249.54

Perfectly located to enjoy all that Southern Pines and Pinehurst have to offer⛳️ Sleeps up to 8 with 4 Queen Sealy Posturpedic beds with luxury linens. All the bedrooms have 43 smart TVs and charging ports for your electronics. A 65 smart TV in the living room is just the place to watch your favorite movies and sports. Fully stocked kitchen. Outdoor seating on the front porch and back deck. Seasonal community pool. Garage game room including 10ft putting green, foosball and darts.

UnForegettable Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$521.39

Treat your family to an unforgettable vacation at this 4-bedroom, 3.5-bath home in Southern Pines. The vacation rental's gourmet kitchen is the perfect place to whip up breakfast for the day ahead. Come afternoon, relax poolside while the kids enjoy the backyard. Tee off at Southern Pines Golf Club, admire the beauty of the Sandhill Horticultural Gardens, and catch a flick at the Sunrise Theater. In the evening, head downtown for local fare and a drink at Hatchet Brewing Company.brbr-- THE PROPERTY --brbrPet Friendly w/ Fee | ~ 3 Mi to Downtown | High-Speed Internet Access brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bunk Bed | Additional Sleeping: Twin Air Mattress, Toddler MattressbrbrINDOOR LIVING: High chair, Smart TV, office w/ monitor, board games, fireplace, dining tablebrOUTDOOR LIVING: Furnished patio, heated pool (depth 4.0’-8.0’, open May 1st - September 30th), gas grill, private yardbrKITCHEN: Dishwasher, gas stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, spices, blender, coffee grinder, coffee maker, toaster, KitchenAid stand mixer, trash bags & paper towelsbrGENERAL: Free WiFi (230 Mbps), central A/C & heating, in-unit laundry, complimentary toiletries, linens & towels, keyless entry, hair dryer, hangers, iron & boardbrFAQ: 3 stairs for entry, 2-story home, 1st-floor bedroom & bathroom, pet fee (paid pre-trip)brPARKING: Driveway (6 vehicles), free street parking (first-come, first-served), RV/trailer parking allowed on-sitebrbr-- THE LOCATION --brbrTHINGS TO SEE & DO: Reservoir Park (1.7 miles), Sandhill Horticultural Gardens (2.6 miles), Sunrise Theater (2.8 miles), Downtown Southern Pines (2.9 miles), The Splash Pad (5.7 miles), Weymouth Woods - Sandhills Nature Preserve (5.9 miles), Rockingham Speedway (22.5 miles), Aloha Safari Zoo (26.0 miles), Uwharrie National Forest (32.3 miles), Morrow Mountain State Park (56.3 miles)brHIT THE LINKS: Pine Needles Golf Club (1.4 miles), Talamore Golf Course (2.1 miles), Southern Pines Golf Club (4.0 miles), Hyland Golf Club (4.2 miles), Pinehurst Golf Course (6.2 miles)brWINE + BREWS: Southern Pines Brewing Company (2.3 miles), Hatchet Brewing Company (3.3 miles), Pinehurst Brewing Company (6.0 miles), Railhouse Brewery (6.4 miles), Black Rock Winery (8.2 miles) brAIRPORTS: Fayetteville Regional Airport (42.6 miles), Raleigh-Durham International Airport (68.8 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires 3 exterior stairs for entry. While there is 1 bedroom and 1 full bathroom on the 1st floor, additional stairs are required to access the 2nd-floor bedroomsbr- NOTE: The seasonal pool is only open from May 1st to September 30thbr- NOTE: The pool is not kept above 80°br- NOTE: The pool is professionally serviced weekly; guests are prohibited from adjusting equipment, settings, valves, timers, or adding chemicals to the poolbr- NOTE: Guests may use the hose to add water to the pool if neededbr- NOTE: Any damages or service calls resulting from tampering with pool equipment will incur additional charges

Peaceful Southern Pines Home w/ Pool + Yard!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$1803.45

Welcome to The Albatross – A signature golf trip experience located in the heart of the Pines! Comfortably sleeping 16+ at 4,000 square feet of living space with a custom designed private backyard brbr*Golf Simulator Lounge Experiencebr*Custom Pool & Patiobr*2,500 Sq ft Short Game Complexbr*Massage Chairs to Recoverbr*Outdoor Fire Pit, Wood is Providedbr*Pool Table, NFL Blitz, Arcade Gamesbr*8 Person - Felt Poker Tablebr*Two Refrigeratorsbr*55”+ TV’s in most roomsbrbrWelcome to The Albatross! A signature golf trip experience located in the heart of the Pines! Custom built by golfers, for golfers. Centrally located in the heart of the golfing paradise only minutes away from the top courses in the area. brbrThis house comes designed from the ground up with golf focused amenities to craft your perfect group trip on and off the course. There are several amenity highlights in this vacation rental such as the indoor simulator and training facility. Whether you want to improve your swing, play games like closest to the pin and compete with friends through the night, or simply enjoy playing some of the world`s most famous courses, the simulator is the perfect way to do it in the comfort of your own home. brbrStepping out back into the private outdoor area is a 2,000 sq ft patio & pool that is overlooking a 2,500sq ft short game complex with three tiers of synthetic professional turf to shape shots from, or select from two tee boxes.brbrThe outdoor pool is open year round but not heated. Usually warmer temps from April to October or take the plunge throughout the fall and early spring. And for those who want a little more privacy, the private fenced-in yard provides a secluded oasis perfect for grilling or just hanging out.brbrFor the crisp and cool nights, there is a wood burning fire-pit out back with wood provided at no additional cost. brbrBack Inside, the large open concept kitchen allows you to entertain and even dine at home if you want a break from the hustle and bustle, with double ovens and a fully stocked kitchen. Granite countertops wrap the fully equipped appliances and breakfast bar providing a welcome opportunity for informal dining.brbrThe kitchen is completely stocked with all cooking and dining essentials that you’ll need to create up your favorite family recipes. There is ample seating for everyone in your group to enjoy meals together. There is a formal dining table (seats 10) and bar top seating (seats three) in the kitchen and dining area. Just outside of the kitchen is two outdoor patio dining table (seats 12 total, 6 each), which is perfect for enjoying a morning coffee while overlooking the outdoor estate as your friends warm up on the putting greens.brbrSleeping Accommodations – 16 individual beds.brbr*Bedroom 1 – 4 Queens via Adult Heavy Duty Bunks. En Suite Bathroom. br*Bedroom 2 – 1 Queen br*Bedroom 3 – 1 Queenbr*Bedroom 4 – 2 Fullbr*Bedroom 5 – 2 Twin XLbr*Bedroom 6 - 4 Queenbr*Converted Living Room – 2 Queen Pullout Couches if needed.brbrOverall there are 14 total individual regular beds in the house and 3 Couches. 2 of those couches pullout to convert to queen sleeper sofas bringing the total to 16 total beds if utilizing the pullout couches. brbrAll Bathrooms are equipped with linens, toiletries, and refillable shampoo, body wash & conditioners which are mounted in the showers for your use.brbrEntire Home minus one locked linen / owners closet is available for use. Check in information and codes will be emailed 48 hours prior to check in.brbr**Damage Deposit & Waiver**brWe partner with `Truvi` for our guest screening process and rental agreement waiver. The `Truvi` application will be received digitally just after booking and must be completed by the primary guest listed on the reservation. Please note, your booking is NOT covered until these requirements are fulfilled. brbrIn this quick process, guests are required to sign a Rental Agreement that outlines the terms of the stay, which includes agreeing to the following:brbr-Abide by our rental terms and conditions.br-Provide a valid government-issued ID and matching credit card before check-in.br-Pay a non-refundable $35 damage waiver through `Truvi`.br-Host is able to extend and add to this to provide total coverage of all property and contents once activated.brbrTogether, this damage waiver covers accidental damage during your stay. Please note, any damage incurred must be reported during your stay to ensure coverage by the waiver. brbrPlease reach out if any questions or you do not feel comfortable with this process.br- Keep Garage Doors & Windows Shut At All times.br- County Quiet hours from 10pm to 8 am outdoors.br- No Unapproved parties or events. br- No Smoking Indoors. $250 cleaning service applied to resolve odor.

Luxury Golf Retreat - Simulator & Short Game Setup

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$1975.75

Summary:brbrWelcome to the original Birdie House in the home of American golf—our flagship Pinehurst property and the ultimate golf trip headquarters. Designed for players who live for the game, this one-of-a-kind retreat features an elite short-game facility, indoor simulator lounge, curated golf décor and amenities galore. Nestled near the legendary courses of the North Carolina Sandhills, it’s the ultimate destination for those chasing a perfect golf trip.brbrbrbrThe Space:brbrOur 6,000-square-foot short-game complex delivers a tour-caliber practice experience. Built by Celebrity Greens—the team behind backyard greens for Jon Rahm and Max Homa—it features five pin locations, seven tee boxes, and realistic bunkering. The green reacts like a championship surface, and with Callaway wedges and Odyssey putters on hand, you can dial in every shot.brbrbrbrOur simulator lounge pairs the Foresight Falcon launch monitor with PuttView’s augmented reality putting system, creating the most complete indoor golf experience. Finish every hole on a sloped green that mirrors the on-screen shot. With tour-level tracking, real-time putting feedback, and no auto-putts, this setup keeps the competition going long after your round is over.brbrbrbrWith 6 Queen beds and 2 King beds across 5 bedrooms, there is plenty of room for everyone to get a good night's rest.brbrbrbrGuest Access:brbrThe entire property is available for your use. There are 3 locked supply closets throughout the house will will not be accessible during your stay.brbrbrbrThe Neighborhood:brbr3 min:Pine Needlesbrbr5 min:Mid Pinesbrbr6 min:Talamorebrbr7 min:Mid Southbrbr9 min:Forest Creekbrbr22 min:Tobacco RoadbrbrbrbrInteraction with Guests:brbrRyan is your go-to guy on the ground in Pinehurst and is available to ensure your trip is perfect.

Birdie House - Pinehurst

Southern Pines, North Carolina, United States

Bath

12

Sleeps

$437.73

Welcome to Horses & Courses — a veteran-owned home in Southern Pines created to bring people together, slow things down, and make your stay feel effortless from the moment you arrive.brbrWhether you’re here for a golf trip, family vacation, military TDY, or a quiet weekend away, we wanted this home to feel less like a rental and more like the kind of place you instantly settle into. The home features 4 bedrooms, 3 bathrooms, and enough space for families, golf groups, and friends to comfortably gather while still having room to relax and recharge.brbrMornings here are peaceful — coffee in hand before an early tee time at nearby Pinehurst Resort, walks through the quiet neighborhood, or slow starts before exploring everything Southern Pines has to offer. After a long day, come back to comfortable living spaces, cozy bedrooms, and a home designed for good conversations, shared meals, and unwinding together.brbrAs a veteran-owned and operated property, hospitality matters deeply to us. We’ve tried to create the kind of experience we would want for our own family and friends — clean, comfortable, welcoming, and genuine.brbrWe’re proud to share this home and this community with our guests, and we hope Horses & Courses becomes part of the memories you make while visiting the Sandhills.

Horses & Courses - Spacious 4-bedroom house in beautiful Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$243.01

Only two minutes from downtown, you’ll be right by local restaurants, shops, and cultural spots. Spend the day on one of the area’s top golf courses or head out for a scenic walk at Weymouth Woods-Sandhills Nature Preserve. Back at the house, there’s plenty of space to relax and recharge. Whether you’re here for the outdoors, good food, or simply some peace and quiet, our home offers a welcoming retreat where you can make lasting memories with family and friends.brbrWelcome to our charming Southern Pines retreat! This single-level home offers comfort and convenience just a stone`s throw away from downtown. With 4 bedrooms and 2 bathrooms, it`s ideal for families or groups looking to explore the beauty of North Carolina`s Sandhills region!brbrStep inside to discover a cozy living space perfect for relaxing after a day of adventures. The kitchen is fully equipped for whipping up delicious meals, complete with modern appliances and ample counter space. Enjoy your meals in the dining area or sitting around the island. .brbrEach bedroom is designed with your comfort in mind, featuring plush bedding and a closet with ample hangers fro your belongings. The two bathrooms ensure that everyone has their own space to freshen up, whether preparing for a day of golf at nearby Pinehurst or winding down after shopping in downtown Southern Pines.brbrYou will have complete access to the home. We utilize an electronic keypad for access and a code will be sent to you prior to your arrival.brbrNearby Attractions:brbr- Carolina Horse Park Foundation (14.7 miles)brbrWe love interacting with our guests. Looking for area recommendations We`re just a message away.brbrAt Stay Well Vacation Rentals, we are experts in prioritizing the guest experience through unparalleled customer service. We are a locally owned management company and take your vacations seriously. We appreciate how expensive it can be to travel, not only financially but also in cost of vacation days. We want to ensure you have the best vacation possible and we are dedicated to delivering that experience to each guest.

Serene South Henley: Short Drive to Downtown

Southern Pines, North Carolina, United States