358,603 properties available

Located in Southern Pines, Florida, United States. Sienna at The Shire 255 D - Unit B - Downtown! Downtown Living! 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 Downtown 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.Sienna 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. - 400' to The Jefferson Inn (live music on the weekends)- 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) - 0.2 miles to Ashtens - 0.2 miles to The Bel

Located in Southern Pines, Florida, United States. The Gallery - 2 bd Boutique Southern Pines Cottage Enjoy a uniquely designed experience at this centrally-located place - whether in town for golfing, riding, or simply enjoying our quaint southern town. Just a block from Broad street's restaurants, shops, breweries and theatre, this two bedroom, two story cottage (and art studio!) has everything you need to enjoy Moore County. Relax in any of our carefully curated rooms, or take it outside to our backyard/vineyard for a summertime BBQ or a cozy fireside chat.

Located in Southern Pines, Florida, United States. Charming Downtown Cottage Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoor patio, walk around and take in the beautiful sights of this charming Southern town. Just minutes from world-renowned Pinehurst and Pinehurst Village.

Located in Southern Pines, Florida, United States. Cozy cottage close to it all - pet friendly! Enjoy a premium stay at this centrally located place! Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines!

Located in Southern Pines, Florida, United States. Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses. The Downtown Lodge promises a central location in downtown Southern Pines and near Pinehurst. The heart of this residence lies in the kitchen and living area – a central hub where the home boasts its appeal. The kitchen has everything one may need to cook a singular meal or prepare food during extended stays. The living room is equipped with ample seating, a small library, a smart TV, and a record player/Bluetooth speaker to facilitate the experience. In the rooms, you'll find everything needed for a comfortable stay - soft mattresses, and comfortable pillows and sheets.From the convenience of exploring local attractions to the thrill of being close to top-notch golf courses, our lodge offers a unique blend of comfort and accessibility. Whether you're a traveler seeking a beautiful 'Main Street' experience, a golf enthusiast eager to tee off, or someone looking to embrace the charm of small-town America, t

Located in Southern Pines, Florida, United States. Suite Cypress Golf Hideaway. Minutes from Downtown Cozy corner townhome nestled up against Southern Pines golf course hole 5. Spacious for family and friends to join. Suit Cypress is situated in a very quiet neighborhood with plenty of privacy. You will be 5 min from downtown Southern Pines and 12 min from dt Pinehurst. Enjoy all that the pines has to offer, including 40+ golf courses, the renown Pinehurst No. 2 and spa, several breweries for the craft beer connoisseur and cuisine for every foodie. The southern hospitality never disappoints. Pool temp CLOSED.

Located in Pinehurst, Idaho, United States. Million Dollar View w/ 3 masters + Peloton on Pinehurst No. 9 This all-ensuite 3 bed/3.5 bath cottage offers beautiful views overlooking the 8th Hole of Pinehurst National, the prestigious course designed by Jack Nicklaus. Located at the center of the action for Pinehurst and Southern Pines play, Legacy Cottage is one of few stays in this elite, gated community. This gorgeous property is well-equipped and furnished for comfort and convenience. You've found your place to stay... now get ready to relax and unwind!One dog is welcome to stay for a nightly fee of $25 (fee collected after booking with pet agreement). Weight limit is 50 lb. *Note- dog must always remain on a leash when outdoors. The property is not fenced! SERVICE ANIMALS ALWAYS WELCOMEParking is available for 1-2 vehicles at the house; additional parking just down the hill near the clubhouse.Some of this home's amazing features:- 2650 sq ft of space with amazing views of Pinehurst No. 9- Light-and-bright open concept

Located in Southern Pines, Florida, United States. Two blocks from downtown! Charming, cozy home close to everything! Consider this your home-away-from-home! Enjoy your visit to the "land of the pines" by staying in the Timeless Tudor. Capable of comfortably hosting groups of up to 10, this beautifully updated 100 year old home is located just two blocks from downtown Southern Pines and boasts—among its many favorable features—4 comfortable bedrooms, 2 and a half bathrooms, and a private backyard oasis.Plenty of space for larger groups! This home features 4 bedrooms and 2 and a half bathrooms, including a first-floor bedroom (queen) and en suite bathroom. The additional 3 bedrooms (1 king + futon, 1 double, and 1 queen + double) are located on the second floor and share hallway access to the second full bathroom.The well-appointed kitchen and adjoining dining room are perfect for home cooked meals when not enjoying the nearby restaurants. The large but cozy living room offers plenty of seating for everyone to watch a movie or big gam

Located in Southern Pines, Florida, United States. Southern Pines Getaway w/Theater, Fire Pit & Pool Large 4 bedroom and 3 bathroom secluded home in Southern Pines with a swimming pool and very spacious backyard with a fire pit and games. The home also features a theater room with a 70 inch smart TV.Welcome to our spacious 4 bedroom, 3 bathroom home located in the beautiful town of Southern Pines! Our home is perfect for families or groups looking for a comfortable and convenient place to stay while exploring all that the area has to offer.The main floor of our home features a fully equipped kitchen, dining room, two bedrooms, and living room. The kitchen is stocked with all the necessary cookware and appliances to make your stay feel like home. The dining room table seats 6 (but can add more chairs) and the living room has plenty of comfortable seating for everyone to relax. The main bedroom features a king bed and en suite bathroom. The second bedroom has a queen bed and a desk.Upstairs, you will find 2 bedrooms (one with 2 twin XL b

Located in Southern Pines, Florida, United States. Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course One-of-a-kind historical estate overlooking the 15th fairway of the Donald Ross designed Mid Pines Golf Course in Southern Pines. Often described as having one of the ''best'' golf course views in The Sandhills, The Knollwood Manor was built in 1926 and lovingly cared for through the years. The elegance of this English Country Manor exists in concert with 2.06 acres of natural beauty. The sweeping back lawn overlooking the golf course is the perfect setting for entertaining or simply kicking back to enjoy life in The Sandhills. Residence features 5 spacious bedrooms on the second floor, all with private bath. Bedrooms facing the golf course have sleeping porches with additonal twin beds. Gourmet Kitchen, 2 fireplaces, hand-molded plaster ceilings & walls and the dramatic Formal Dining Room for large gatherings. Numerous historical architectural elements include original oak hardwood flooring, original slate

Located in Southern Pines, Florida, United States. New! The Mulligan in Downtown Southern Pines Located just quick walk from downtown Southern Pines, our spacious modern home is the ideal home base for a golf retreat or a family holiday. The house is newly built and outfitted with everything your group will need to have a comfortable, fun, memorable stay!*10 mins to Pinehurst Resort*5 mins to Southern Pines, Mid Pines, & Pine Needles Golf Clubs*2 min drive or 15 min walk to restaurants, bars, & shops of downtown Southern PinesThe property features:AMPLE PRIVATE PARKINGThe house sits on a corner lot and the driveway wraps from the front of the house to the back, providing plenty of room for your vehicles.TWO LIVING AREASThe light-filled downstairs living area is open to the kitchen and dining spaces. It features a super comfy leather sectional, a huge smart TV, and a gas fireplace.The upstairs living area is a cozy hangout space by day and three additional sleeping spaces by night. Two daybeds, setup as a sectional sofa, convert into tw

Located in Southern Pines, Florida, United States. New! Insane Golf Retreat & Simulator - Bogey Bunks This house was built from the ground up to create the perfect golf trip to accomodate several foursomes with everything that is important for your visit to the Pines from golf games, table games, or lounging. Maximize every minute of your next vacation on and off the course. Included is a fully heated/cooled space with a Simulator, Gameroom & Loft. Enjoy a closest to the pin challenge or add some rain insurance in case you need to wait out some weather and still want to get a round in!The Bogey Bunks sits on 1.9 private acres with no HOA, is equipped with 2 Game rooms, 5 Bedrooms hosting 14 Beds, 3 Full Bathrooms, a Kitchen stocked for 20, and indoor and outdoor dining opportunities.Amenities Included:+Indoor Golf Simulator+Outdoor Putting Green+Outdoor Fire Pit & Patio+Pool Table+8 Person Poker Table+Ping Pong +Coffee Bar+Outdoor Dining & Grill+String-lights & Patio Lighting+Privately Tucked 1.9 AcresThe Simulator is a fully heated

Located in Southern Pines, Florida, United States. 11-Standard Guest Room - 2 Queens · The Jefferson Inn Rm. 11 Welcome to The Jefferson Inn, Room 11! A Standard guest room featuring two queen beds newly refreshed as of March 2023.From the cottage style furniture, to the luxurious linens to the rain shower head, you will feel pampered by the amenities and comfort features of our beautifully appointed accommodations. Within walking distance to all of the charm Southern Pines, NC has to offer! We can't wait to welcome you.The Jefferson Inn is a digital entry hotel, so guests will have swift and easy access to the building and their unit!There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Pinehurst, Idaho, United States. Stunning Golf Views on Pinehurst National No. 9. A Luxurious Retreat Awaits. Welcome to your luxurious retreat at Pinehurst National No. 9! Nestled alongside the picturesque 9th hole, this exquisite home offers unparalleled views of the lush greenery and serene water features of the golf course.Step inside to discover a haven of relaxation and entertainment. With four spacious bedrooms, each boasting two large beds and its own connecting bathroom, this home comfortably accommodates large groups with ease. Sink into the plush comfort of your bed after a day of golfing or exploring the charming surroundings.The heart of this home lies in its expansive living spaces designed for ultimate enjoyment. Gather with friends and family in the stylishly furnished living room, complete with ample seating and a flat-screen TV for movie nights or catching up on your favorite shows.For those who love to entertain, the fully equipped kitchen beckons with its modern appliances and generous counter spa

Located in Southern Pines, Florida, United States. Standard Guest Room- 2 Queens · The Jefferson Inn Rm. 13 Welcome to the historic Jefferson Inn & 1901 Lounge in beautiful Southern Pines, NCRoom 13 is one of our lovely standard guest rooms featuring two queen beds, cottage style furniture, a smart TV, luxurious linens, premium coffee and an oversized bathroom with walk-in shower and rain shower head. You will certainly feel pampered by the amenities and comfort features of our accommodations for the duration of your stay.Make sure to visit 1901 Lounge in the lobby for a delicious speakeasy-style experience, craft cocktail and local bite! Open Tuesday - Saturday.The Jefferson Inn is a digital entry property, allowing guests ease of check-in and check-out.Book today and experience all the historic charm a trip to Southern Pines, NC has to offer - we can't wait to welcome you.There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Southern Pines, Florida, United States. Standard Guestroom - 1 King · The Jefferson Inn Rm. 6 Welcome to The Jefferson Inn & 1901 Lounge in beautiful Southern Pines, NC.Room 6 is a spacious standard guest room featuring a King bed. From the cottage style furniture, to the luxurious linens, to the spacious bathroom, you will feel pampered by the amenities and comfort features of our accommodations for the duration of your stay.Our standard guest rooms are furnished with a walk-in shower with both regular and rain shower head.The Jefferson Inn is a digital entry property, allowing guests ease of arrival and departure.Book your stay today and experience all the historic charm Southern Pines has to offer.The Jefferson Inn is a digital entry property, allowing guests ease of arrival and departure.There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Southern Pines, Florida, United States. Standard King Guestroom · The Jefferson Inn Rm. 10 Welcome to The Jefferson Inn & 1901 Lounge!Room 10 is a standard guest room featuring a king bed. This guestroom features a walk-in shower with both a regular and rain shower head.From the cottage style furniture, to the luxurious bed and linens, you will feel pampered by the amenities and comfort features of our accommodations for the duration of your stay.Make sure to visit 1901 Lounge, entrance located in the lobby, for a speakeasy-style craft cocktail and local bite during your stay.Come experience all the charm Southern Pines, NC has to offer with a trip to The Jefferson Inn - we can't wait to welcome you.The Jefferson Inn is a digital access property, allowing guests ease of entry. There is an onsite concierge who will take lovely care of your during your stay!There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Southern Pines, Florida, United States. Standard Guestroom (ADA) - 1 King · The Jefferson Inn Rm. 8 Welcome to The Jefferson Inn & 1901 Lounge in beautiful Southern Pines, NC!Room 8 is an ADA accessible standard guestroom featuring a King bed.From the cottage style furniture, to the luxurious linens, to the spacious bathroom, you’ll feel pampered by the amenities and comfort features of our accommodations. The Jefferson Inn is a digital entry property, allowing guests ease of both arrival and departure.Make sure to visit 1901 Lounge, located in the lobby, to enjoy a speakeasy-style craft cocktail and local bite during your stay.Book your stay today and don't miss the historic charm of Southern Pines, NC right out your front door! We can't wait to welcome you.There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Southern Pines, Florida, United States. The Cottage at Knollwood Manor Relax at The Cottage, a private getaway situated on the Knollwood Manor estate next to the 15th Fairway of Mid Pines Golf Course. This quaint and cozy cottage is stocked with all of the necessities and conveniences to relax in The Pines and is situated at the ideal location for easy access to all local attractions.King bedroom and on-suite full bathroom, full kitchen, living room and small dining area, washer, dryer, separate half bathroom, and various other unique features and amenities. Also included is a futon and chaise couch to sleep 4 people if needed.Security and Safety measures are in place, to include deadbolt locks, CO and smoke alarms, outdoor lighting, fire extinguisher, first aid kit, and outdoor security cameras to monitor entrance, driveway and parking areas.

Located in Southern Pines, Florida, United States. Charming Southern Home - close to Pinehurst Golf and Downtown Southern Pines Escape to this charming 4-bedroom, 3-bathroom home that comfortably sleeps 10, nestled in a peaceful neighborhood just 5 miles from Pinehurst #2 and 1.5 miles from downtown Southern Pines (walkable). Outdoor LivingOur large screened-in porch with a 7-person hot tub is a highlight, offering a perfect spot for morning coffee or evening gatherings. Outdoor furniture and a gas grill invite you to unwind, soak up the sun, and savor al fresco meals. A part of our backyard is fully fenced-in.Don't worry about overpacking; our vacation home comes equipped with a washer and dryer for your convenience. The fully stocked kitchen has everything you need to prepare meals, whether you're whipping up a quick breakfast or preparing a gourmet dinner for your group.- 4 bedrooms, 3 full bathrooms- Sleeps 10- Huge screened-in porch with hot tub and ceiling fan- Fully fenced-in outdoor area- Hot tub and infrared sauna- Quiet neigh

Located in Southern Pines, Florida, United States. Deluxe Guestroom - 2 Queens · The Jefferson Inn Rm. 4 Welcome to The Jefferson Inn & 1901 Lounge, in beautiful Southern Pines, NC.Room 4 is a deluxe guest room that features two queen beds and all of the luxurious comfort you can come to expect from a stay at The Jefferson, including an oversized bathroom, luxurious linens and rain head shower.The Jefferson Inn is a fully digital access property, allowing guests ease of entry.Make sure to visit 1901 Lounge, located in the lobby, to enjoy a speakeasy-style craft cocktail and local bite during your stay!Book today and come experience the history and culture of The Jefferson Inn in Southern Pines, NC - we can't wait to welcome you.There will be a $300 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Located in Southern Pines, Florida, United States. Historic 1890 Cottage in the Heart of Downtown Southern Pines, NC! This historic 1890 renovated cottage in downtown Southern Pines with hot tub & private fenced outdoor living space has every thing you need for an amazing travel experience. You’ll be just 1 to 3 block walking distance from breweries, restaurants, bars, and shopping while being within a few miles drive from world renowned golf courses in Pinehurst. Acorn Cottage is the perfect location to enjoy all that Moore County has to offer!!

Located in Southern Pines, Florida, United States. Elegant golf get-away 4 minutes to Pinehurst. Surrounded by Golf Opportunities! Play the links or visit (4 miles) historic Pinehurst or Southern Pines. Relax in elegant, spacious home. Enjoy the outdoor park setting featuring gardens, comfortable spaces, dining pavilion, fireplaces, decks and swings.

Located in Southern Pines, Florida, United States. 2024 US Open at "The Pines" "US Open Golf Retreat: Minutes from Pinehurst!Immerse yourself in the excitement of the US Open at our spacious and centrally located rental property, located just minutes from the tournament grounds. This space offers the perfect blend of comfort and convenience, with modern amenities to ensure a memorable stay. Whether you're cheering on your favorite golfers or exploring the vibrant surrounding area, our rental provides the ideal home base for your US Open experience!