Vacation rentals with a pool in Pinehurst

4.79 out of 5 average rating, 38 reviews

An outdoor area features a stone patio surrounding a sparkling inground pool. Comfortable seating is provided by several lounge chairs and a patio table shaded by an umbrella. A fire pit is positioned centrally, with brick walls enhancing the space and landscaped greenery in the background.

Home in Carthage

Welcome to the Castle, Private Pool spacious

Must be at least 25 to book. Rental Agreement and security deposit required. Additional guest fee over 14 guests No 3rd party bookings. Disclosed pet fee with approval, $500 undisclosed pet fee, $50/hr late check out fee. No one night reservations less, 5 min for holidays. Cancellation Policy 100% (less $100.00 cancellation fee) if cancellation occurs at least 60 days before arrival; No refunds within 60 days of arrival. $500 refundable security deposit required. POOL HEAT AVAILABE NO CHARGE

A spacious living area features a combination of comfortable seating, including a sleek sofa and armchairs. A modern coffee table sits atop a patterned area rug, with natural light filtering in through large windows. The open layout connects seamlessly to the kitchen area.

4.9 out of 5 average rating, 84 reviews

Pinehurst Retreat for Golf Trips | Pool + Space

"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.

5.0 out of 5 average rating, 78 reviews

An aerial view of a serene backyard features a bright blue saltwater pool surrounded by comfortable seating and umbrellas. A hot tub is positioned nearby, and a firepit sits within a gravel area. Lush trees provide a natural backdrop with gentle lighting accentuating the space.

Home in Southern Pines

ThePalmerOnTheGreen*Pool*HotTub*FirePit*CentralDr

The Palmer is a private luxury retreat overlooking the golf course. Unwind in the saltwater pool or hot tub, relax on the front porch, back deck, or covered patio, enjoy the beautifully lit backyard with ambient string lighting perfect for evening gatherings. Complimentary coffee, tea, hot chocolate, a variety of snacks, and wine. We have ample parking, a wide selection of indoor & outdoor games for guests of all ages. Minutes to DTSP, Pinehurst, local dining, shopping, and world-class golf

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, 48 reviews

Pinehurst Playground on the Lake POOL OPEN!

Make Pinehurst your playground both on the links and at the lake! Bring your fishing pole and bathing suits for both our lake and pool access (May-Sept). We are located 1 mile from the famed Pinehurst Resort which is home to the 2024 US Open. Numerous other courses are within a 30 minute drive. There is no shortage of quality golf around here! Our place is perfect for a group golfing weekend, a family trip, US Kids golf tournaments, or a weekend spent shopping and enjoying the spa.

4.87 out of 5 average rating, 52 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 fire pit surrounded by rustic Adirondack chairs is positioned on a stone patio. Soft glowing lights hang from a nearby tree, illuminating the tranquil atmosphere. In the background, a heated pool is visible, reflecting the serene night sky.

5.0 out of 5 average rating, 30 reviews

Walk to Village: Heated Pool Hot Tub Putting Green

The Enchanted Escape feels a little like discovering a place someone forgot to tell everyone else about located just steps from the Village of Pinehurst. Three distinct residences surround a backyard designed around reconnecting. Mornings with coffee in rocking chairs. Pool afternoons that somehow stretch longer than expected. A putting green that quietly turns competitive. Reclaimed treasures, collected details, and spaces that keep making people say, "Wait...come look at this."

4.87 out of 5 average rating, 23 reviews

A private pool is surrounded by a brick terrace, framed by lush green foliage. Two decorative stone planters add character at the entrance, while sun loungers are positioned nearby for relaxation.

Cottage in Pinehurst

Tremont Cottage | Private Pool | 2blk DT Pinehurst

Welcome to Tremont Cottage, a historic gem in downtown Pinehurst. - Four bedrooms, including two master suites and three full baths - Furnished with period antiques and hand-knotted rugs - Private pool with a fenced backyard and cozy fire pit - Large game room with pool table and board games - Beautiful brick terrace with lush landscaping - Fully equipped kitchen with granite countertops and stainless appliances - Complimentary drip-brewed and Keurig coffee makers

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, 177 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, 40 reviews

Home in Foxfire

The Ultimate Golf Trip House - Pool & Pickleball

Escape to Foxfire in the Pinehurst area enjoy a luxury lakefront estate for large groups and unforgettable stays. With a pool (May to Mid-Sept), hot tub, sauna, cold plunge, golf simulator, game room, pickleball/basketball court, and 2 full kitchens, there’s something for everyone. Sleeping up to 24 guests across 12 beds, this retreat features putting greens, fire pit, outdoor pizza oven, and multiple decks overlooking the lake--perfect for relaxing and making memories.

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 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

POOL OPEN! Enjoy newly renovated 2BD,2BA condo

Welcome to the Magnolia Hideaway in Pinehurst! It is our hope that our beautiful, renovated & very clean , condo is a place you can rest, unplug, and enjoy time together. VERY IMPORTANT ! PLEASE READ!! Beds can be converted into either 2 KINGS, 4 TWINS, or 1 KING and 2 TWINS. BED CONFIGURATIONS NEEDS TO BE REQUESTED AT TIME OF BOOKING! The STANDARD SET UP is as following: 1 KING BED in Primary BDR and 2 TWIN BEDS in second Bedroom.

4.96 out of 5 average rating, 186 reviews

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.

Popular amenities for Pinehurst rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 85 reviews

Peaceful Place sleeps 16 , Pool, Hot tub, Sauna

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, 25 reviews

25 McQueen - 4 Bedroom House with Pool

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, 53 reviews

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

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.

4.94 out of 5 average rating, 53 reviews

Convenient Golf & Private Pool Getaway

5.0 out of 5 average rating, 8 reviews

Home in Southern Pines

Le Pin Tordu: A Pinehurst Retreat

Home in Southern Pines

Branch & Pine | Private Pool + Near Pinehurst Golf

New place to stay

Pinehurst Area Oasis with Hot Tub and Pool

5.0 out of 5 average rating, 5 reviews

40 Caddell

Condo rentals with a 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

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, 89 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

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, 91 reviews

Stunning Lakefront in Pinehurst with pool!

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 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.

4.66 out of 5 average rating, 32 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

4.8 out of 5 average rating, 10 reviews

2BD 2BA Condo Minutes from Pinehurst Resort

5.0 out of 5 average rating, 3 reviews

250 Sugar Gum Lane #208

Other vacation rentals with a pool

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

4.98 out of 5 average rating, 63 reviews

Townhouse in Southern Pines

UnForegettable Stay in Southern Pines

5.0 out of 5 average rating, 44 reviews

Apartment in Southern Pines

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

5.0 out of 5 average rating, 4 reviews

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!

5.0 out of 5 average rating, 67 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

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