Vacation rentals with a pool in Southern Pines

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Southern Pines

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in Pinehurst

5 out of 5 average rating, 13 reviews

Miley's Place at Pinehurst

Welcome to Miley's Place at Pinehurst! This recently updated 2 bedroom 2 bath condo features incredible views with sunsets over the lake and is literally across the street from world-class golf. Refresh yourself in the community pool (open seasonally) after a day on the greens, or simply take a hot shower in one of the well-appointed bathrooms. Miley's Place has a well-stocked kitchen, comfortable furniture, and is convenient to both Pinehurst and Southern Pines. Enjoy Miley's Place. Cheers!

Superhost

Home in Carthage

4.58 out of 5 average rating, 12 reviews

Welcome to the Castle, Private Pool spacious

Must be at least 25 to book. Rental Agreement and security deposit required. Additional guest fee over 6 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 ADDITIONAL CHARGE

Guest favorite

Townhouse in Southern Pines

5 out of 5 average rating, 24 reviews

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.

Guest favorite

Condo in Pinehurst

4.92 out of 5 average rating, 123 reviews

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

Our condo is centrally located in the quiet and scenic Lakeview Condominium Community - only minutes away from Pinehurst Resort and CC and the charming Village of Pinehurst. Located on the second floor, this 2BR/2BA unit offers a very comfortable and restful stay. Whether you're taking in the gorgeous sunset from the balcony, a winding stroll through the community, or some down time at the private pool, our hope is that you find pleasure in every moment that you're here!

Guest favorite

Cottage in Pinehurst

5 out of 5 average rating, 10 reviews

Tremont Cottage | Private Pool | 2blk DT Pinehurst

Perfectly located in the heart of downtown Village of Pinehurst and walking distance of Pinehurst Course #2. The exquisite Tremont Cottage is rich in history and tradition and is only a one minute walk from a unique combination of cultural, recreational, dining, and shopping experiences. The Tremont has a private pool with a fenced in backyard, gas fire pit, outside dining table, and a pool table inside. This Cottage provides memorable experiences and comforts of home.

Guest favorite

Home in Pinehurst

5 out of 5 average rating, 37 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.

Guest favorite

Condo in Pinehurst

4.96 out of 5 average rating, 79 reviews

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.

Guest favorite

Home in Aberdeen

4.92 out of 5 average rating, 111 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.

Guest favorite

Home in Southern Pines

4.84 out of 5 average rating, 25 reviews

Carolina Comfort-Walk DT,2 BR,Fireplace,huge yard

Relax and unwind at this charming home located in Southern Pines! Enjoy your stay within walking distance to locally owned boutiques, restaurants, breweries, and more! Avail yourself to the Sandhill's most renowned golf courses followed by an escape to The Spa At Pinehurst just 10 minutes away. After a day of exploring "The Pines", catch some rays by the crystal clear pool in the spacious backyard!

Guest favorite

Home in Southern Pines

4.96 out of 5 average rating, 120 reviews

Highland Hideaway/Pool & Fire Pit/$0 Cleaning Fee

Nestled in a peaceful neighborhood just a few miles from downtown Southern Pines and multiple world-renowned golf courses ⛳️ . A 3-bedroom / 2.5-bathroom home with a bonus room. Spacious open porches overlook an inground pool, perfect for those hot summer days, and a fire pit, perfect for relaxing during the evenings. This home is also a short drive to Fort Liberty and surrounding hospitals.

Guest favorite

Condo in Pinehurst

4.88 out of 5 average rating, 49 reviews

Pinehurst 2Bedroom 2Bathroom Condo with Lakeview

Relax with the whole family or with your foursome at this Golfer's dream location! Located right on Lake Pinehurst, 5 minutes from PCC main clubhouse. Enjoy the view from the balcony or hit the community pool! - Lakeview is the only condominium community with a private pool (open Memorial Day thru Labor Day). - Washer/Dryer in unit available. - Full kitchen. - 2nd floor unit.

Guest favorite

Rental unit in Pinehurst

5 out of 5 average rating, 9 reviews

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.