Holiday rentals with a pool in Orange County

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!

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)!

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.

Amazing Retreat: 55 Acres of Nature + Pool + Pond

4100sf GUEST SPACE ON 55 ACRE COUNTRY ESTATE FARM Come enjoy the self-contained 4100sf 6BR very private guest area in our 7000sf Country Estate Home located only 20 to 25 minutes to Duke & UNC. Ultra luxurious Custom Home with beautiful views of nature.. Pool, fire pit, trail & acres of pastures to roam. High end furnishings with contemporary flair. Designer's personal home & no expense spared to create a one-of-a-kind oasis for folks to come & enjoy. NO PARTIES OR EVENTS ALLOWED.

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

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 (closed 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!

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.

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.

Gorgeous Mid-Century Home with Pool

This newly styled mid-century gem in Chapel Hill will wow you! Our spacious 4-bedroom home boasts a private pool, vaulted ceilings, and lush wooded views. With multiple living areas and luxurious amenities like a steam shower, it's the perfect private retreat for families and groups. Experience architectural beauty and modern comfort just minutes from UNC and local trails, comfortably accommodating your entire group. **Please Note: You must be 25+ years old to book this property.**

Spacious 2BDR Condo + Wifi + UNC Vacation Rental

My space is a charming rental in Chapel Hill, tastefully furnished and conveniently located for travelers visiting Chapel Hill or other nearby areas for leisure and work. The 2 bedroom, 2 bathroom, single-story rental has all the guest amenities and space you'll need to enjoy your stay in Chapel Hill! You'll love our guest amenities. In addition to free parking, you can enjoy guest essentials and Netflix. Our home is on people’s minds. Save us to a wishlist!

The Durham III • Vibe 8726

Step into The Durham III, a cozy 1-bedroom, 1-bathroom walk-up on the first floor in Durham, NC. This residence includes a kitchen, Wi-Fi, air conditioning, and access to a gym and pool, providing a comfortable stay for two guests. Step into The Durham III, a cozy 1-bedroom, 1-bathroom walk-up on the first floor in Durham, NC. This residence includes a kitchen, Wi-Fi, air conditioning, and access to a gym and pool, providing a comfortable stay for two guests.

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.

Cozy 2-bed, 2.5 bath near UNC

The townhome is nestled in a cul-de-sac neighborhood and is part of a larger townhome complex that has access to a clubhouse, pool, tennis court, basketball hoop, and doggy play area. The property provides direct access to the Bolin Creek trail for walking, running, and biking. The townhome is a short, 0.3 mile walk to the town/university bus stop and a 10-minute drive to UNC Hospital.