Vacation rentals with a pool in Hillsborough

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Hillsborough

Nightly prices starting at
Hillsborough vacation rentals start at $110 per night before taxes and fees
Verified guest reviews
Over 350 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hillsborough rentals
4.9 Average rating
Hillsborough stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Hillsborough

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

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Top guest favorite

A serene outdoor area showcases a rectangular swimming pool surrounded by smooth stone decking. Comfortable lounge chairs are positioned for relaxation, while lush greenery and trees provide a natural backdrop. The exterior of the multi-level house features large balconies and a welcoming red door.

Guest suite in Hillsborough

4.96 out of 5 average rating, 194 reviews

Luxe Guest Suite w Pool (Historic, Downtown)

Southern charm is in abundance in this c. 1799 home! This sun-filled, artfully restored space is a private, "in-law" suite adjacent to a sprawling southern Estate. You'll enjoy a private entrance, huge living area / queen bed, large dressing room with "his and hers" vanities, modern bathroom with walk-in shower and oversized tub, access to gorgeous pool, and sprawling verandas. The space is mere blocks from all that quintessential historic Hillsborough has to offer, and is a rare treasure!

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Top guest favorite

A single-story cabin is nestled among tall trees, featuring a wooden facade with a steep roof. A welcoming front porch is adorned with a hanging plant, and colorful flowers are arranged along the pathway leading to the entrance. Natural surroundings enhance the setting.

Guesthouse in Hillsborough

5.0 out of 5 average rating, 116 reviews

Charming Cabin with Private Wooded Pond

The Cabin is situated near our home on 67 woodland acres, 15 min. from Hillsborough and 25 min. from Duke University and UNC-Chapel Hill. The Cabin is a converted horse barn with lofted ceilings, kitchenette, living area, dining table, bathroom, outdoor patio, and bedroom area separated by a partial wall. The pool and swimming pond are a few steps away. You are welcome to canoe, fish, walk our trails, play disc golf, or just enjoy the peaceful views. Ideal for couples and business travelers.

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Top guest favorite

Guesthouse in Raleigh

4.99 out of 5 average rating, 203 reviews

Relaxing Saltwater Pool Oasis and Modern Retreat

Come relax in our centrally located modern escape. This garage top apartment is drenched in natural light & includes all the extras. The open floor plan living, dining, and kitchen is perfect for couples, friends, and business travelers looking for upscale accommodations. Our salt water lounge pool is open to guests June-Oct. NEW traditional sauna is open year-round. Walk to the beautiful Five Points Neighborhood. 10 mins by car to downtown or NC State campus, and 20 mins to RDU airport

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Top guest favorite

Three horses of varying colors are seen standing near a wooden fence in a spacious pasture. A covered shelter is located in the background, while a clear blue sky with scattered clouds accentuates the serene landscape.

Farm stay in Hillsborough

4.91 out of 5 average rating, 144 reviews

Horse farm, serene, secluded, creekside suite

Welcome to Strouds Creek Farm. Charming 2BR 1 bathroom suite w/cozy farmhouse decor. Located on 20 picturesque acres nestled in the woods. Enjoy peaceful mornings filled with bird songs. Stroll around the farm to meet & greet our "fur family". Relax in a hammock, explore the creek or sit on the swing & enjoy the farm fresh air. Just 5 minutes from downtown Hillsborough, an artist's paradise, dotted with art galleries, boutiques, a bookstore & restaurants. 15 min. to Duke & downtown Durham.

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Guest favorite

A modern living area features two stylish green sofas facing a contemporary electric fireplace, with a large flat-screen TV mounted above. Natural light floods the space through two windows, while a sleek coffee table holds a decorative bowl and chess set.

Home in Durham

5.0 out of 5 average rating, 134 reviews

LUXE Home 4 Mins Duke/DPAC | King Beds, BBQ, Pool

Make unforgettable memories in this spacious, beautifully designed home for you + 9 guests! Perfect for family gatherings, sporting events, & special occasions. Located in heart of Downtown Durham, just 4 mins from Duke, Bulls stadium, DPAC, & Tobacco Trail. Cozy up around the fire pit, enjoy a BBQ, or relax w/fresh popcorn & vinyl records. Retire in luxurious beds + sheets & head to the gourmet coffee bar in the AM. Free access to nearby gym w/pool. 4 air mattresses and EV charger avail.

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Top guest favorite

A tranquil salt-water pool is surrounded by lounge chairs and vibrant red umbrellas. A pergola with seating is visible in the background, along with well-maintained landscaping and an inviting patio area. The clear blue sky enhances the serene environment.

Farm stay in Hurdle Mills

4.98 out of 5 average rating, 228 reviews

Luxury Retreat on Farm with Pool, Hot Tub, Fishing

LUXlife Best Luxury Country B&B Retreat in NC! 120 acres of peaceful farmland with an in-ground salt-water pool, hot tub, pergola, pastures, farm animals, fresh eggs, streams, woodlands, fishing, and hiking. Private hot tub at rental. The heated, salt-water pool and hot tub are located behind the owner's home. You’ll have total privacy. Wholesale pasture-raised Wagyu beef and lamb available at the farm as well as fishing in the stocked pond. Propane grill and pizza oven on your patio.

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Guest favorite

The front of the home features a charming exterior with blue shutters and a welcoming entrance. Lush purple flowers bloom vibrantly in the landscaped yard, complemented by green shrubs and a small tree. A driveway is visible, leading to the side of the house.

Home in Durham

4.79 out of 5 average rating, 129 reviews

Spacious 3bd Lake & pool near Duke UNC Southpoint

Our home is a very comfortable and spacious 3 bedroom -2.5 bath perfect for families. The bedroom are spacious each with own TV. It has a full kitchen , laundry closet with washer and dryer. Outdoor deck area with outside sitting & bbq facilities upon request .Living room for the family gather .Our location: steps from wonderful walk around the lake.and community pool for the summer travelers Conviniently located near Duke urgent care- Southpoint , Duke , UNC & Tabacco trail.

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Top guest favorite

A serene view of a wooded area with a gently winding pond, bordered by lush greenery. The landscape features a glimpse of recreational amenities, including a swimming pool nestled among trees, offering a peaceful retreat in the countryside.

Dome in Snow Camp

4.99 out of 5 average rating, 151 reviews

Countryside Getaway UniqueDomeA/serenefarm retreat

Welcome to our serene countryside farm glamping dome, nestled in the heart of nature on a sprawling 28-acre property. Perfect for a peaceful getaway, our dome offers a unique blend of comfort and adventure.Escape the hustle and bustle of city life and relax under the stars. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, our property offers the perfect setting for a memorable experience. Discover the beauty and tranquility of countryside living.

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Top guest favorite

Guesthouse in Raleigh

4.95 out of 5 average rating, 457 reviews

Raleigh Oasis Close to it All

The pool is OPEN and ready for the 2026 season! Don't forget to pack a swimsuit. An owner-occupied private residence with a large private saltwater pool and guesthouse above the detached garage. Enjoy the sights and sounds of a stocked koi pond or observe nature from the private balcony. Minutes from Rex Hospital, Crabtree Mall, Art Museum and PNC arena. The location cannot be beat! Feel far from the city while close to all the things Raleigh/Durham have to offer.

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Superhost

The charming exterior of the cottage is shown, featuring a well-maintained lawn and landscaped flower beds. A concrete walkway leads to the front door, framed by lush greenery and trees in the background.

Home in Chapel Hill

4.79 out of 5 average rating, 157 reviews

UNC Cottage- near Univ/Hospital, YMCA, Franklin St

This beautifully decorated 2 bed/1 bath home is a treasure. Our kitchen is fully stocked and ready for gourmet cooking. The cottage sleeps 4 people. Each bedroom has high speed wifi and a desk. The living room is perfect for reading books or watching movies on our Smart TV. The renovated bathroom has stunning tile floors and a tile shower/tub. Enjoy our large deck. See if you can spot our family of 6 deer who call our woods home.

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Top guest favorite

A serene backyard is framed by lush greenery and features a pristine saline pool with bench seating. Several deck chairs are arranged under large umbrellas, and the nearby wooden fencing adds a sense of privacy.

Guesthouse in Durham

5.0 out of 5 average rating, 204 reviews

Chic Poolside Hideaway Near Duke & UNC

Tucked away in the back of our 1927 property sits The Sidekick, a thoughtfully restored carriage house surrounded by peaceful woods & grand homes. Part cowboy clubhouse, part restful retreat, The Sidekick is a conveniently-located getaway for couples, solo travelers, or small groups. Take a dip in the saline pool, lounge in the mature garden, or just rest your sleepy head on luxurious linens in your sweet lil' loft bedroom.

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Guest favorite

A spacious bedroom is showcased with a comfortable bed dressed in crisp white linens. A plush blue throw adds a touch of color, complementing the vibrant blue wall. Nightstands with soft glowing lamps flank the bed, enhancing the space's relaxing ambiance.

Apartment in Downtown Durham

4.82 out of 5 average rating, 113 reviews

100 Year Old Historic Brick 2BR Loft High Ceiling3

Party Policy: To ensure a great experience for everyone, parties are not allowed. Violations of house rules such as excessive noise, smoking, or additional unapproved guests will result in a $300 fee, reservation cancellation, and removal from the property. If that works for you, please send an inquiry or instant book — we’d love to host you! Booking Requirement: Guests must have at least 3 reviews on their profile.

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