Holiday rentals with a pool in Pinehurst

Walk to Village: Heated Pool Hot Tub Putting Green

Experience the magic of Pinehurst at The Enchanted Escape, a meticulously restored historic estate nestled on a private 1 acre lot, just a short stroll from the charming Village. This exceptional property offers a unique blend of vintage elegance and modern luxury, providing an unforgettable getaway for discerning travelers seeking space, privacy, and unparalleled hospitality. Perfect for groups, our property comfortably accommodates up to 10 adults across three beautifully appointed structures.

GolfThePalmerOasis*Private* SaltwaterPool*HotTub

Welcome to The Palmer, a peaceful Southern Pines retreat with serene golf course views, a sparkling saltwater pool(for a Polar Plunge)outdoor spaces perfect for relaxing or spending time with family. We warmly welcome military families and offer a comfortable setting for small gatherings, such as work or family events, while maintaining a no-large-party policy. Just minutes from Pinehurst, shops, and restaurants, The Palmer combines comfort, convenience, and a welcoming atmosphere for all guests

Cheerful Pinehurst home tucked away with a pool.

"Whitty Fox" is a large, updated home away from home, perfectly suited for a group golf trip or family get away. This beautifully appointed home, set in a peaceful part of Pinehurst, is just 1.3 miles from Pinehurst Village, and has both fine dining and a breakfast/ lunch restaurant close by. 8 people can have their own beds in this home that can sleep upto 14, and each of the 4 bedrooms has an en suite bathroom. + 2 twin beds in a bonus room. it’s perfect for reunions, & multi-family stays.

Lakeside Escape - 5 Miles from Pinehurst Resort

5 miles from the Pinehurst Resort - Escape to a Lakeside Retreat - where comfort and adventure collide! This 4-bedroom gem sleeps 10 and boasts a cozy gas fireplace, big-screen TV, and free weight gym for staying active. Relax by the pool, paddle across the lake, or fish from the private beach. End your day by one of 3 outdoor fireplaces. With kayaks, a paddle boat and comfortable accommodations, fun and rest are endless. Perfect for unwinding or making memories—your retreat awaits!

Lakefront Pinehurst Condo 2BD/2BA - 114

Beautiful Lake Pinehurst property only 1-2 miles from the clubhouse at Pinehurst Resort, the "Cradle" par 3, & the Pinehurst Spa. The community of Southern Pines is only a few miles away which offers additional fine dining & shopping. 1st floor condo Swimming Pool in Complex for guests open May-August. Smart TV in living room & primary room Wifi Keurig Coffee Maker Microwave Stack Washer & Dryer Unit Due to owners allergies, no pets including service animals are allowed.

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool CLOSED for the season** Welcome to Lakeview Landing, located in the heart of Pinehurst golf! With a second story view of Lake Pinehurst, guests can relax on the balcony or enjoy the community pool! This quiet neighborhood shares close proximity to several great golf courses and has easy access to the BEST parts of Pinehurst: historic downtown, Fair Barn + Harness Track, Pinehurst Resort + Clubhouse, etc. Plus, it's a quick drive to nearby Southern Pines + Aberdeen!

Pinehurst Golf Retreat | Near Cradle & Resort

Breathe in the calm of Pinehurst at this updated 3BD/2BA condo beside Course No. 5 — just minutes from the Pinehurst Village, Pinehurst Fair Barn and world-class golf. Perfect for families and golf groups alike! Enjoy a fully stocked kitchen, cozy living space with a basket of games, and thoughtful family touches like a high chair and pack ’n play. Spend your days exploring the greens, shopping in the Village and watch the sunset through the pines from your private patio.

The Pinehurst Paradise Pool Home

Your family will be close to everything when you stay at this centrally-located home. Only minutes from the Pinehurst Resort & C.C. and village! I have been told my home is happy, fun, cozy, homey yet very clean and accommodating. Enjoy swimming in the pool, chipping golf balls on to the floating green, playing corn hole, and watching the outdoor TV while grilling out or lounging in a pool float! There is a covered gazebo with curtains and a gas fire pit.

Stunning Lakefront in Pinehurst with pool!

Enjoy the amazing views of Lake Pinehurst in this spacious newly renovated first floor 3 bed, 2 bath condo. This home has everything you need for a short or long term stay. Living room, master and second bedrooms have stunning lake front views! Condo complex features a pool and is only 2 miles away from the village and golf club. Perfect for a golf foursome or family looking for extra space. Kayak and paddleboard also available for guest use.

Country living 10 mins to Horse Park, Golf & Town.

Quiet, country living only 10 mins from shopping, restaurants, The Carolina Horse Park & golf! Enjoy the quiet neighborhood, the serene atmosphere & within 10 mins, you can be walking into 1 of many great restaurants or shopping centers. Enjoy grilling on the back deck, lounging in the pool or taking nice walk on the private road. House was completely remodeled 2 years ago & offers an open floor plan with 2 living rooms.

The Suite Spot

This centrally located suite is the perfect spot for your next visit to Pinehurst. Come and enjoy the views from the back covered porch, book a tee time at one of Pinehurst’s world renowned golf courses, soak up some North Carolinian vitamin D and then take a dip in the pool, or simply stay indoors and let The Suite Spot be your sweet respite from the world.

Pinehurst - Lakeview 2BR w/pool

Peaceful 2BR condo in Pinehurst with lake views and brand-new furnishings and access to the community pool. Come enjoy local golf as a player or a spectator in this beautifully appointed unit. Enjoy sunsets on the back deck with views of Lake Pinehurst. This unit is also close to downtown Pinehurst and the Fair Barn where many local events take place.