Holiday rentals with a pool in Pinehurst

4.99 out of 5 average rating, 218 reviews

Guest house in Carthage

Charming 1 bedroom guesthouse on 4 acres, hot tub

Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee for dogs. sorry, no cats.

4.92 out of 5 average rating, 137 reviews

THE NEST, 2BDR 2BA, 2nd Floor, WiFi, Cable, Pool

Our condo is centrally located and hugs the majestic shores of Lake Pinehurst! It’s tucked away at the top of the statuesque Lakeview Condominiums! So peaceful and quiet and yet only minutes away from Pinehurst Resort and CC, the charming Village of Pinehurst, and a plethora of great pubs and restaurants! Located on the second floor, this 2BR/2BA unit offers our guests gorgeous sunsets, quiet strolls, and the simple pleasure of green living! Come and be our guest! 🐾🌳

Guest house in Southern Pines

4.98 out of 5 average rating, 46 reviews

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.

Superhost

4.56 out of 5 average rating, 34 reviews

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

Retreat to Pinehurst for a relaxing golf getaway when you book this 2-bedroom, 2-bath vacation rental! Conveniently located near Pinehurst Resort - scheduled to host the 2024 US Open - this home base allows easy access for practicing your swing and catching up with friends on the green. Stroll through the Village's shops, eateries, parks, and museums, or lounge on the private balcony while enjoying lake views. Whether you’re out and about or laying low, you’re sure to love this condo!

4.93 out of 5 average rating, 74 reviews

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.

5 out of 5 average rating, 26 reviews

ThePalmer*HotTub*SaltwaterPool*Golf*Games*FirePit

The PALMER is a Breathtaking 3-bedroom, 2.5-bath RETREAT. Relax in our brand-new PRIVATE HOT TUB or take a refreshing dip in the SALTWATER POOL! Have fun with friends and family roasting marshmallows on the firepit, playing croquet, horseshoes, disc golf, cornhole or by relaxing in the backyard hammock or on the front porch swing. Whether you’re here for a romantic getaway, family vacation, or a special celebration, The Palmer is designed to create unforgettable memories.

4.94 out of 5 average rating, 119 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!

Guest house in Southern Pines

4.94 out of 5 average rating, 208 reviews

Mystical Cottage

A warm cozy guest house with an open floor plan, high ceilings, and a wall of glass doors overlooking the pool and jungle like backyard of 3 acres. It has a large separate bath and complete kitchen. It was a perfect place for a completely secluded getaway ... less than 2.5 miles from the center of both Southern Pines and the Village of Pinehurst... 8 minutes from nearly every restaurant in the area. We are pet friendly, but charge a seperate $35 pet cleaning pet.

5 out of 5 average rating, 41 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.

5 out of 5 average rating, 40 reviews

3BD Condo with pool surrounded by Pinehurst Golf

Welcome to "The Walter Hagen on Pinehurst No. 5", just off Pinehurst Lake, located in the very heart Pinehurst golf, and just 3 minutes from the world-famous Pinehurst Resort & Country Club, in the heart of Pinehurst, NC. This brand new renovated and rare 3BD, 2BA condo is in the perfect location just off Pinehurst No. 5, and only steps to Pinehurst Lake. Enjoy a truly relaxing location just minutes to everything the Village of Pinehurst has to offer!

5 out of 5 average rating, 131 reviews

Newly renovated 2BD,2BA condo,Free Pool, Cable etc

Welcome to the Magnolia Hideaway! 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 Main BDR and 2 TWIN BEDS in second Bedroom.

4.92 out of 5 average rating, 118 reviews

Home in Aberdeen

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.

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Popular amenities for Pinehurst rentals with a pool

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House rentals with a pool

4.95 out of 5 average rating, 65 reviews

Cheerful Pinehurst home tucked away with a pool.

PatrickRating, 5 stars3 days ago

We loved staying here. Plenty of sleeping arrangements, close to Pinehurst and Southern Pines and all there is to do in the area. We played golf during the day and hung and grilled by the pool in the evenings. Would definitely stay again

5 out of 5 average rating, 81 reviews

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

AndrewRating, 5 stars1 week ago

This was our second stay at Nate and Stacy’s. Our family felt so comfortable and the pool was an even bigger hit this year!

Superhost

Home in Foxfire

4.71 out of 5 average rating, 14 reviews

Luxurious Pine Manor: Golf Front Estate with Pool!

StephenRating, 5 stars1 month ago

Wonderful large home with a private feel. Easily can accommodate a large group with plenty of bathrooms and bedrooms. The backyard was great with plenty of seating, large deck and nice pool. Felt very private with the golf course directly behind the property. House was very clean throughout and had all the essentials one needed to cook large meals. Grocery stores all within a 20min drive which was very nice. Overall gladly would stay again, host was very responsive with any questions.

Superhost

4.88 out of 5 average rating, 16 reviews

25 McQueen - 4 Bedroom House with Pool

LucretiaRating, 5 stars1 week ago

This place was everything that it stated pictures did not lie the was location was nice and secluded , the pool was the best part for me and family the house was just enough space inside and out and kitchen was amazing I personally loved it

5 out of 5 average rating, 66 reviews

Southern Pines Getaway - Pool, Hot Tub & Fire Pit

PaulRating, 5 stars1 month ago

6 guys visiting their childhood buddy who moved to the area a few years ago. The house was a perfect home base for us. Just perfect. Open layout, pool after a long day of playing golf, plenty of rooms for privacy, perfect location to all the golf clubs and breweries, bars, restaurants. Daniel and Ruth were super responsive to our needs. Highly recommended to large groups or for families. 🙏🤝

4.93 out of 5 average rating, 30 reviews

Gorgeous Home | Private Pool | Close to Pinehurst

AlexanderRating, 5 stars2 weeks ago

Excellent place! Service was outstanding. House is better than pictures or descriptions. Would definitely stay here again.

4.84 out of 5 average rating, 38 reviews

Dive Into The Pines-walk DT, new pool, fenced yard

AmandaRating, 5 stars2 weeks ago

We loved our weekend getaway here! The house is adorable and the pool was perfect for a hot afternoon!

5 out of 5 average rating, 19 reviews

Spacious property w/Pool & walkable to downtown

JohnRating, 5 stars2 weeks ago

We stayed here for a golf trip with a group of 8 and the place worked out great. The house was clean, spacious, and had plenty of room for everyone to spread out and relax after long days on the course. The outdoor space with the pool was a nice bonus, and the kitchen had everything we needed for meals and drinks at home. Location was quiet and convenient for getting to the local courses. Communication with the host was easy, and check-in was smooth. Would definitely consider booking again for a future trip.

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Apartment rentals with a pool

Apartment in Jackson Springs

5 out of 5 average rating, 13 reviews

Par In The Pines

JeffryRating, 5 stars4 weeks ago

Andrea's place fit all of our needs! we are familiar with the area and needed a place to stay while visiting family. Andrea's place checked all the boxes! we will definitely be back if she'll have us! Thank you! Jeff and Linda Jorinscay

4.81 out of 5 average rating, 54 reviews

Pinehurst 2Bedroom 2Bathroom Condo with Lakeview

DanielleRating, 5 stars3 weeks ago

Jeremy is a fantastic host, quick to respond and very helpful. I would absolutely recommend staying here. I loved being on lake and loved having that view was everything.

4.7 out of 5 average rating, 54 reviews

Renovated 2-bedroom/2 bath condo with pool access

DonnaRating, 5 stars8 months ago

End unit , very private. everything needed provide. highly recommend! partial view of lake that was very nice. close to everything! loved the well stocked kitchem

4.98 out of 5 average rating, 45 reviews

Perfect for families! Pool & year round lake views

JesusRating, 5 stars1 month ago

Great place to stay. Definitely will be coming back

5 out of 5 average rating, 93 reviews

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

LindseyRating, 5 stars3 weeks ago

We were in town for a wedding with our kids. The pool was great. It was a quiet and beautiful neighborhood, and about a 7 minute drive to Pinehurst Country Club. Would definitely stay here again.

5 out of 5 average rating, 16 reviews

Pinehurst Playground on the Lake POOL OPEN

MichaelRating, 5 stars3 weeks ago

Great place to stay if you are in the area. Close to lots of things to see and do. I highly recommend.

4.96 out of 5 average rating, 79 reviews

Stunning Lakefront in Pinehurst with pool!

KristinRating, 5 stars9 months ago

Our family all gathered for my son’s wedding - we had more than enough room! Enjoyed our morning coffee on the back porch overlooking the lake. It was extremely peaceful! The pool was terrific, as well as being so close to the club house and the fair barn!