Holiday rentals in Pinehurst

4.95 out of 5 average rating, 240 reviews

Guest Favorite Condo w/ Golf Views! Clean + Comfy

Welcome to your cozy Pinehurst retreat! Whether you're here for a golf tournament, a quick getaway or a longer stay, this clean, comfy ground-floor condo is a great home base. Enjoy a well-stocked kitchen, inviting furnishings + a screened porch with fairway views - perfect for morning coffee or evening wine! It's very close to the historic Village with shops + dining, plus the fair barn, harness track + Pinehurst resort/clubhouse. With its peaceful, well-located setting, it's a guest favorite!

4.89 out of 5 average rating, 100 reviews

Swing Inn the Pines - 2BR/2BA on Pinehurst No. 5

Convenient location within a few minute walk to Pinehurst Resort Clubhouse and Cradle short course. Cozy and updated Pinehurst golf condo w/ modern decor and new furnishings. A spacious 2 bedroom / 2 bathroom (4 beds) in quiet surroundings awaits to enjoy the tranquil beauty of Pinehurst. - Keyless Entry - On-site Parking - First Floor Unit - New Furnishings - Poker Table - Fully Equipped Kitchen - 2 Covered Patios - Golf Putting Mat - Hi-speed WiFi, 3 Smart TVs - Kid-friendly w/ pack n’ play

4.98 out of 5 average rating, 115 reviews

Villa in Pinehurst

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

4.97 out of 5 average rating, 100 reviews

Cottage in Pinehurst

Historic cottage in the heart of Pinehurst Village

Historic, newly-restored cottage in the heart of the Village of Pinehurst. The Pink House was built by the Tufts family in 1930, and has lovingly been restored to its original beauty with the addition of many modern amenities. Walking distance to some of the country's most desirable and world famous golf courses, The Pink House is a golfer's dream location. After a long day of golf relax outside by the fire pit, or walk to some of the Village's best restaurants, bars and shops.

Guest house in Southern Pines

4.98 out of 5 average rating, 242 reviews

Historic Southern Pines Carriage House

Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

4.99 out of 5 average rating, 115 reviews

Flat in Pinehurst

Upscale 1 BR condo on Pinehurst #3 & #5

Well appointed 2nd floor 1 BR condo nestled within Pinehurst #3 and Pinehurst #5 courses! A short 15 min walk to Pinehurst Village. Main Pinehurst Resort Clubhouse (Pinehurst #2) is a short walk across the fairway and Beulah Hill Rd. Equipped with a full kitchen. Bedroom has a comfortable queen bed and a flat screen TV. Spacious living room with sofa that folds out to a queen bed. 4K Smart TV with easy access to Netflix, Amazon, YouTube & VUDU. Wi-Fi included.

4.98 out of 5 average rating, 786 reviews

Home in Pinehurst

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

4.92 out of 5 average rating, 296 reviews

Cottage in Pinehurst

Water Oaks Cottage - Near Pinehurst Country Club

Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.

Guest suite in Southern Pines

4.96 out of 5 average rating, 245 reviews

Golf Resort, Private Entrance, Bath & Kitchenette

This Condo is located on Talamore Golf Resort and is minutes away from many world class golf courses, to include Pinehurst Resort. Approximately 40 minutes to Fort Bragg for Military/DOD civilians who are TDY or house hunting; 4 miles to First Health Moore Regional Hospital for travel nurses; 2.5 miles to Sandhill community college; Reservoir Park is a 250 yard walk from the front door and includes a 95 acre lake, and more than 12 miles of Greenway Trails.

4.99 out of 5 average rating, 149 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

4.99 out of 5 average rating, 109 reviews

The Lucky Lie - Entire Condo in Pinehurst

Come relax at the luxurious Lucky Lie! This beautifully renovated studio condo is located just off the beaten path on Pinehurst No. 3, but still perfectly situated for an easy approach into downtown Pinehurst and the surrounding Sandhills. Unwind after your rounds on the porch over looking No. 3, 16th fairway, relax in front of the electric fireplace, or knock out some work in the dedicated workspace, the Lucky Lie has what you're looking for!