Condo holiday rentals in Pinehurst

4.83 out of 5 average rating, 304 reviews

The Perfect Lie in Pinehurst!

This is the perfect getaway spot for enjoying all that Pinehurst has to offer. Situated on fairway 2 of #5, this is a sweet golfer's retreat, walkable to Pinehurst Country Club and the Cradle! Walk across the street for breakfast at the Harness Track or take a short stroll to the Village. This 2bedroom unit is completely private with 2 double beds in each room plus a sleeper sofa. Laundry facilities are just outside the unit in a building across the parking lot. Dogs welcome. No cats please.

5 out of 5 average rating, 115 reviews

Newly renovated farmhouse style open concept.

Completely renovated, stylish 3-bedroom condo is perfect for group trips & Junior golf families. Newly renoved with wide open floor plan in main living area. Gourmet kitchen, 3 incredibly comfortable bedrooms and 2 brand new stunning bathrooms. Includes private laundry room in condo, coffee bar, big screen TV’s in every room, built in bench area in kitchen, very spacious living and dining area off open concept kitchen, and screened in porch out back. Condo is walking distance to The Cradle.

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

4.99 out of 5 average rating, 119 reviews

Long Drive On No. 5 - 1BR Condo, GREAT Golf Views

Renovated, centrally located condo in Pinehurst - only a 10 minute walk to the Pinehurst Golf Clubhouse! "Long Drive On No. 5" is a newly renovated, second-story one-bedroom condo perfectly located on hole #16 of Pinehurst No. 5 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy & luxurious finishes combined with an excellent location make this condo perfect for a weekend golf getaway or an extended stay!

Superhost

4.95 out of 5 average rating, 112 reviews

"Perched in Pinehurst"

Should you decide to visit the picturesque town of Pinehurst, then look no further? Perched in Pinehurst, is less than a half mile from The Pinehurst Resort, and is nestled between Golf Course #5 and The Harness Track. If you are attending a function at The Fair Barn, driving will be optional, because you can easily walk across the street. In addition, you will find plenty of wonderful shopping and dining opportunities nearby. Check out my social media page "Perched in Pinehurst"

4.93 out of 5 average rating, 181 reviews

Condo in Southern Pines

Relaxing in the Pines

Located 5 min from downtown Southern Pines (Broad St). A great place to stay for golfers, horse lovers, and others visiting to explore Pinehurst, Southern Pines and other surrounding areas. The large screened in porch off of the living room and dinning room which provides peaceful beauty and elegance. Two bedrooms and two full baths, this condo provides you with a wonderful opportunity for anyone wanting to relax and especially for golfers, horse lovers and others..5 PM Check in

4.95 out of 5 average rating, 149 reviews

Fairway Condo

This updated condo is located on the 17th hole fairway of the Pinehurst No. 5 Golf Course. It is perfect for golfers as well as travelers visiting Pinehurst area. It is minutes away by car to the Pinehurst Clubhouse and local restaurants. It features a 55 inch smart television in the living room, and a television and two double beds in each bedroom. It also features a custom built golf bag rack to keep your equipment safe and secure during the night.

4.99 out of 5 average rating, 116 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!

5 out of 5 average rating, 121 reviews

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

Enjoy your stay at a fully renovated 2BR/2BA condo right across from Pinehurst's historic Fair Barn and Harness Track. Situated on No. 5, a short approach shot from the Pinehurst Clubhouse, the Duffer's Drop has everything you need for your golf getaway. Relax on the porch overlooking No. 5, work on your culinary skills in the beautiful kitchen, or just catch some rest between rounds. The Duffer's Drop is the exactly what you're looking for!

4.94 out of 5 average rating, 263 reviews

Fairway to Heaven - 2BD 2BA Golf Front Condo

Welcome to Fairway to Heaven, located within walking distance of the Pinehurst clubhouse and Village of Pinehurst! With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 minute drive to the Fair Barn and Harness Track and a 10 minute drive to charming downtown Southern Pines.

4.95 out of 5 average rating, 244 reviews

Guest Favorite Pinehurst Golf Condo! Clean + Comfy

Welcome to your cozy Pinehurst retreat! This clean, comfy ground-floor condo is perfect for a golf trip, weekend getaway, or extended stay. Enjoy a well-stocked kitchen, comfy furnishings, and a screened porch with fairway views—great for coffee or wine. Just minutes to the Village, shops, dining, the Fair Barn, harness track, and Pinehurst Resort. Peaceful, walkable, and a guest favorite!