Holiday rentals with a pool in Southern Pines

5.0 out of 5 average rating, 12 reviews

Le Pin Tordu: Near Pinehurst, Hot Tub, Fenced Yard

End of summer special! French country three bedroom with hot tub and two fire pits. Located just 3 mins to downtown Southern Pines and 10 mins to Pinehurst golf: you cannot beat the location! Le Pin Tordu is a perfect retreat for those visiting Pinehurst/Southern Pines for golf, travel nursing, equestrian, military and much more. Relax in the hot tub or in the serene back yard with the beautiful twisted pines above you. Enjoy the setting and delight in your retreat. We can’t wait to host you!

Townhouse in Southern Pines

Mulligan Fair-Way, a golf retreat -Southern Pines.

Welcome to Mulligan Fair-Way, a golf-inspired retreat in the heart of Southern Pines, where every stay feels like a second shot at unforgettable memories. ⛳ Just like golf, the best experiences deserve a mulligan—and this is a place guests love coming back to, round after round. Perfectly located near some of the most iconic golf courses in the Sandhills, this home is designed for golfers, friends, and families who appreciate great company, relaxed vibes, and the joy of replaying a great trip.

4.83 out of 5 average rating, 12 reviews

4.99 out of 5 average rating, 87 reviews

Peaceful Place sleeps 16 , Pool, Hot tub, Sauna

The ultimate getaway! 3 mi. from Pinehurst Country Club & close to So. Pines. Enjoy a relaxing & fun stay in a newly built home. This spacious home has 4 bd rooms, 3 baths, sofa sleeper,Kit./dinning/living rm, laundry. The sun rm has a Sauna & foosball table. Outside you can swim in the large pool, grill & relax in the lounge area with sofa, dinette and unwind in the Spa. The yard is fully fenced in by a 6 ft. Privacy fence. There is also a grill,swing set,trampoline, fire pit and chairs.

A spacious outdoor area features a large swimming pool surrounded by sun loungers with blue and white stripes. A covered cabana offers shaded seating, with a patio featuring a dining table and chairs. Lush greenery and a white fence enhance the private setting.

4.97 out of 5 average rating, 33 reviews

Pool*Sleeps 20*Stylish*Games*Close to Everything!

Our stylish ranch is perfect for large groups & retreats. Sleeps up to 20 with 10 beds. 5 bedrooms, 4 bathrooms on a 1 acre lot with a swimming pool, game room, firepit, and putting green! Our 1 acre lot feels secluded, but is close to everything! -5 mins to restaurants, nightlife and shops in Downtown Southern Pines -5 mins to Southern Pines Golf Club & Weymouth Center Venue -15 mins to Pinehurst Resort -10 mins to Pine Needles Lodge and Golf Club -10 mins to Mid Pines Inn & Golf Club

Townhouse in Southern Pines

UnForegettable Stay in Southern Pines

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.

5.0 out of 5 average rating, 44 reviews

Guesthouse in Southern Pines

A spacious bedroom showcases a contemporary design with a large bed adorned in a black and white patterned duvet. A cozy seating area with bright pillows is positioned beside the bed. A wall of shelves displays decorative items, with lamps providing warmth and a pleasant ambiance.

Charming Getaway Carriage House with pool

Welcome to our peaceful guesthouse in Southern Pines, NC! This contemporary retreat offers a serene escape with a pool, charming gazebo, and stunning views of the championship golf course, Pine Needles. The spacious unit is decorated in a modern style, providing a comfortable and inviting ambiance. Relax poolside or take a stroll through the well-manicured grounds. Golf enthusiasts will delight in the proximity to the renowned course. Discover tranquility and luxury in this hidden gem.

4.98 out of 5 average rating, 65 reviews

4.87 out of 5 average rating, 54 reviews

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!

A private backyard is shown, featuring a swimming pool with clear blue water surrounded by a concrete deck. Lush green grass extends across the yard, with trees providing a natural backdrop. The house is visible in the background, enhancing the serene outdoor setting.

4.95 out of 5 average rating, 56 reviews

Convenient Golf & Private Pool Getaway

Welcome to your getaway in Aberdeen, NC! This spacious home is perfect for families or groups, featuring 3 bedrooms (1 queen bed, 1 full bed, 1 twin bed, plus an air mattress) and 2 bathrooms. Enjoy a private backyard and grill. Conveniently located just 15 minutes from Pinehurst's golf courses and 20 minutes from the Carolina Horse Park. Amenities include a fully equipped kitchen, laundry facilities, remote check-in/out, WiFi, and a private driveway. Book now for a relaxing stay!

A spacious community pool is surrounded by lounge chairs, with a pergola providing shade in the background. Lush trees line the area, and the clear blue water reflects the sunny sky, creating a serene outdoor setting for relaxation.

4.91 out of 5 average rating, 181 reviews

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool OPEN 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!

5.0 out of 5 average rating, 60 reviews

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.

A rectangular pool with clear blue water is surrounded by a concrete patio. A pool ladder is visible on one end. In the background, a structure with stairs and a mobile home can be seen, along with several tall pine trees providing shade.

4.92 out of 5 average rating, 135 reviews

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.

A cozy living area is presented with a blend of soft gray sofas and armchairs arranged around a wooden coffee table. A decorative rug lies beneath, complemented by a wall clock and tasteful wall art. Natural light enhances the welcoming atmosphere.

5.0 out of 5 average rating, 142 reviews

Beautiful renovated 2BD,2BA Pinehurst condo, Pool

Our beautifully renovated, exceptionally clean 2BR/2BA condo is perfect for relaxing and unwinding. A special feature of The Magnolia Hideaway is our flexible bed setup: • 2 King beds • 4 Twin beds • 1 King + 2 Twin beds Standard setup: 1 King in the primary bedroom + 2 Twins in the second bedroom. For a different bed configuration, please request it at booking so we can have everything ready for your arrival.

Popular amenities for Southern Pines rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The entrance features a stone pathway leading to a welcoming front door adorned with a wreath. Potted plants flank either side of the entrance, and the surrounding greenery adds to the home's inviting exterior.

5.0 out of 5 average rating, 30 reviews

Spacious property w/Pool & walkable to downtown

An outdoor pool area features a crystal-clear swimming pool with a fun slide, surrounded by lounge chairs and shaded tables. A black fence encircles the area, offering privacy. Umbrellas provide shade over the seating, complemented by green landscaping in the background.

5.0 out of 5 average rating, 54 reviews

Family Fun, Pool, Hot Tub, Sauna, ZipLine, 3King B

An open-plan living area features a spacious dining table surrounded by six upholstered chairs. A modern kitchen with an island is visible, showcasing new appliances and sleek countertops. Natural light streams in through windows, highlighting the warm wood flooring and neutral wall colors.

4.92 out of 5 average rating, 26 reviews

25 McQueen - 4 Bedroom House with Pool

Branch & Pine | Private Pool + Near Pinehurst Golf

Pinehurst Area Oasis with Hot Tub and Pool

The exterior of the home is framed by tall pine trees, with a long driveway allowing ample parking space. The two-story house features a light-colored siding and large front windows. Neatly trimmed shrubs and flower pots enhance the inviting curb appeal.

4.98 out of 5 average rating, 111 reviews

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

5.0 out of 5 average rating, 6 reviews

40 Caddell

5.0 out of 5 average rating, 3 reviews

Pinehurst Retreat | Near The Cradle & Village

Condo rentals with a pool

The living area features a dining table surrounded by four chairs and a comfortable sectional sofa. Two armchairs are positioned by large glass doors that offer views of Lake Pinehurst. Soft natural light illuminates the space, complemented by neutral-toned décor.

4.93 out of 5 average rating, 90 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

A spacious living area is presented with a large, dark sectional couch complemented by assorted cushions. A circular wooden coffee table is positioned in front, and natural light enters through expansive glass doors that offer views of the outdoor space. A small area rug and bookshelf enhance the comfort.

5.0 out of 5 average rating, 49 reviews

Pinehurst Playground on the Lake POOL OPEN!

A comfortable living area features a sectional sofa and two armchairs. A coffee table and round dining table are arranged with chairs, providing ample seating. Large sliding doors open to a balcony with views of Lake Pinehurst, framed by light-filtering curtains.

4.84 out of 5 average rating, 69 reviews

Pinehurst 2Bedroom 2Bathroom Condo with Lakeview

A serene view of Lake Pinehurst is presented, with calm waters reflecting the surrounding trees and blue sky. The image captures several well-maintained buildings along the water's edge, creating a peaceful lakeside atmosphere.

4.95 out of 5 average rating, 92 reviews

Stunning Lakefront in Pinehurst with pool!

A game room is presented with a slate pool table positioned centrally, flanked by two framed vintage sport posters on the walls. Soft beige carpeting covers the floor, and natural light enters through large window treatments, contributing to the welcoming ambiance.

4.96 out of 5 average rating, 52 reviews

Perfect for families! Pool & year round lake views

A modern living area features a spacious sectional sofa and a leather ottoman, with a view overlooking Lake Pinehurst through large sliding glass doors. Natural light floods the room, complemented by artwork on the wall and minimalistic furnishings.

4.61 out of 5 average rating, 33 reviews

Pinehurst Lakefront Condo: Ground Floor Condo

The living area features hardwood floors with natural light flowing through large windows. A spacious gray sectional sofa is arranged around a coffee table, complemented by a dining table with light-colored chairs. Decorative plants add a touch of greenery to the space.

4.98 out of 5 average rating, 102 reviews

Renovated, Ground Level 2BR2BA, WiFi, Cable, Pool

5.0 out of 5 average rating, 3 reviews

250 Sugar Gum Lane #208

Other holiday rentals with a pool

Apartment in Southern Pines

Quiet and cozy! *Perfect studio you’ll love*

5.0 out of 5 average rating, 4 reviews

The guest house features a bright exterior with a welcoming porch adorned with black and white chairs. A flag is displayed, and lush greenery surrounds the area. The pool reflects sunlight, complementing the serene atmosphere of the jungle-like backyard.

Guesthouse in Southern Pines

Mystical Cottage

4.9 out of 5 average rating, 218 reviews

5.0 out of 5 average rating, 68 reviews

A spacious outdoor pool is surrounded by a chain-link fence, with several lounge chairs arranged along its perimeter. Lush green grass and trees frame the area, while multiple buildings can be seen in the background, contributing to a serene environment.

Apartment in Carthage

Golf Getaway, 5 miles to Pinehurst

5.0 out of 5 average rating, 30 reviews

A charming cottage exterior is presented, featuring a vibrant green front door framed by large windows. Two rocking chairs are positioned on the porch, and potted plants add greenery. A brick pathway leads up to the entrance, complemented by neatly arranged landscaping.

Cottage in Pinehurst

Great for Families of Jr. Golfers!

A serene view of a fenced seasonal pool area is seen, surrounded by lush greenery. A sunset casts a warm glow above, enhancing the tranquility of the scene. A sign indicating the pool's private status stands to the right, framed by neatly maintained shrubs.

5.0 out of 5 average rating, 6 reviews

Lakefront 3BR/2B near Pinehurst Resort

A bright living area is filled with natural light, featuring a comfortable seating arrangement with a sofa and decorative pillows. A glass coffee table sits on a colorful area rug, while a dining table is positioned nearby, framed by large windows showcasing views of the lake.

4.5 out of 5 average rating, 40 reviews

Lakeview Condo w/ Resort Pool: 2 Miles to Golf!

A spacious living area features a gray sofa, accent chairs, and a glass coffee table. Large sliding doors provide natural light and scenic views of the outdoors. A dining table is set with blue placemats and white napkins, enhancing the inviting atmosphere.

Apartment in Pinehurst

The Pinehurst Perch

4.86 out of 5 average rating, 14 reviews