Holiday rentals with a pool in Orange County

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Top-rated rentals with a pool in Orange County

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

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Top guest favourite

Farm stay in Hillsborough

5 out of 5 average rating, 53 reviews

Eye of the Rooster Farm

Steve and Angel welcome you to a cozy apartment at our farm surrounded by nature. Less than 5 miles from historic Hillsborough, UNC Hospital Hillsborough campus, and less than 15 miles from Duke/UNC university campuses. Enjoy fresh eggs for breakfast from our chickens and fresh vegetables grown on the property (seasonal). Relax at the pool area. This is a common space shared with the hosts, which are professional, friendly, and mature individuals respectful of others, especially our guests.

Top guest favourite

Guest suite in Hillsborough

4.96 out of 5 average rating, 152 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!

Superhost

Farm stay in Hillsborough

5 out of 5 average rating, 8 reviews

Serenity Cottage

Experience the magical beauty and tranquility of Firefly Farm, a 26-acre flower farm nestled in the lush countryside near the historic town of Hillsborough, North Carolina. Immerse yourself in farm life. Stroll our paths and visit our farm animals. Take part in our seasonal delights: flowers bloom April to September, fireflies glitter at dusk during Summer while birds and butterflies delight during the day and Fall brings crisp air as the leaves change (as well as Witch Hazel's haunted barn)!

Guest favourite

Farm stay in Hillsborough

4.91 out of 5 average rating, 107 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.

Guest favourite

Home in Durham

5 out of 5 average rating, 28 reviews

Lg Pool House w/ Hot Tub Central to RTP*Pool Open*

Discover luxury in this AAA five-bedroom Durham home near Duke Hospital and Duke University. Perfect for family reunions, corporate stays, or small weddings, it features spacious living areas with tasteful decor, a fully-equipped kitchen, and a dining room for memorable meals. Outside, enjoy a private pool (open for the season) and hot tub (open year round) for relaxation. Explore nearby attractions like Duke Gardens and the vibrant Durham arts scene. Ideal for creating lasting memories!

Top guest favourite

Apartment in Chapel Hill

5 out of 5 average rating, 45 reviews

Willow-Updated Chapel Hill Condo w/ Community Pool

**Pool CLOSED 2025 for refurbishing** Your family will be close to everything when you stay at this centrally-located 2 bedroom condo. Enjoy this quiet diverse community with just a walk across the street to Harris Teeter, restaurants, movie theater, and the local farmers market at University Place, & Free transit. 5 minute drive to UNC campus, Dean Dome, Keenan Stadium, and UNC hospitals. With I-40 less than 2 miles away, you will have quick & easy access to Duke University and RTP.

Top guest favourite

Farm stay in Hurdle Mills

4.98 out of 5 average rating, 201 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.

Superhost

Home in Chapel Hill

4.9 out of 5 average rating, 21 reviews

North Carolina Charm

Perfect location, spacious, one story with all the amenities to make your stay comfortable. Less than 15 min away from UNC Chapel Hill with close and easy access to free Chapel Hill buses! Groceries, dining & shopping less than 10 min away. RDU airport 20 min away. Whether you’re looking for a game weekend with 6 other friends, a short walk to visit loved ones at Carol Woods or a place to call home for an extended work trip, North Carolina Charm is what you’re looking for. STR-23-56

Superhost

Guest suite in Chapel Hill

4.76 out of 5 average rating, 152 reviews

Forest Garden Suite - Private studio in the trees!

Lovely townhouse studio in the woods convenient to UNC-Chapel Hill (bus stop is across the street) as well as Durham and RTP (by car). You will be surrounded by greenery in this established neighborhood minutes from Umstead Park and Bolin Creek. Feel free to contact us during your stay for anything you may need including info on our town's numerous top-rated restaurants and fun outdoor activities. We hope you enjoy your stay with us! Chapel Hill Zoning Compliance Permit STR-23-9

Guest favourite

Townhouse in Chapel Hill

4.94 out of 5 average rating, 32 reviews

Charming Modern Townhouse

Discover our 2BR townhome, 8 mins from Chapel Hill. Ideal for families or work stays, it accommodates 5 guests. Enjoy amenities smoke-free environment, free parking, trail access, and a seasonal pool. In the vibrant Winmore neighborhood, offers easy access to the Chapel Hill bus line. Additional features: Smart TV, fast WiFi, standing desk, master bedroom with ensuite, guest room, sleeper couch, and laundry closet. Book your stay for a modern yet tranquil experience.

Top guest favourite

Cabin in Hillsborough

5 out of 5 average rating, 163 reviews

Spacious Poolside Guesthouse on Private Pond

Our 67-acre property, Split Rock, is located 25 min. from Duke University and UNC-Chapel Hill. We are also 15 min. from Carrboro & Hillsborough, a historic, walkable community. Our guesthouse is a large pool cabana with kitchenette & queen bed overlooking a 4.5-acre pond surrounded by uninterrupted woodland. You are welcome to canoe, fish, walk our trails, play disc golf, or just enjoy the peaceful view. Split Rock is ideal for couples and solo travelers.

Guest favourite

Home in Mebane

5 out of 5 average rating, 5 reviews

Quiet home near Lake & Outlets

Quiet 4 bedroom home in Mebane, NC. Whether you're visiting on business or pleasure this home is a great escape. This home boosts walking trails to nearby Lake Michael. Cozy indoor fireplace to unwind after a long day. 5 minute drive to Tanger Outlets, quick commute to UNC, Duke, Elon, UNC Greensboro only 35 minute drive to RDU. Seasonal Pool and Gym access. Complete with everything you need to make your stay worry free.