Holiday rentals with a pool in Oak Island

Modern Oceanfront OKI getaway with Pool

BookSmart Properties presents: A New Tide! This stunning 4‑bed/3‑bath oceanfront retreat offers the best of both worlds: unobstructed ocean views on three sides and added serene views of the Davis Canal. Enjoy the private fenced in-ground pool, private walkway to the beach, and spacious decks perfect for sunrise and sunset views. Inside, the home is designed to maximize coastal views and ambiance, with a layout that offers plenty of space for families and groups to relax and unwind. Book your st

New Beach Home with Pool + Ocean Views, Sleeps 17!

Welcome to the Carolina Brightside on Oak Island! This brand new coastal retreat is located only one row back from the beach and blends charm with modern comfort! With an open floor plan, beautiful natural light, incredible views and your own private pool, this home is designed for effortless group getaways! You will enjoy beach access, local shops and dining and can unwind in a home that brings together relaxation, style, and the perfect touch of island living! Beach access across the street.

Rise and Shine! Beach, pool, & amazing views!

Welcome to RISE AND SHINE at Oak Island Beach Villas! Fabulous location on tranquil Caswell Beach. Close to amazing food, the iconic Oak Island Lighthouse, and top rated golf yet you feel the peaceful vibe of being on the east end of the island. Steps from the beach with breathtaking views, this beautifully decorated condo features 2 bedrooms, 1 bath and sleeps 5-6. Choose a short walk to the pool (seasonal) or simply relax on the private balcony listening to the soothing sounds of the ocean.

OIB~Oceanfront Condo 3 BD/2BA, Linens Included!

3 bd, 2BA Oceanfront Condo in the sought after less crowded West End of Ocean Isle Beach! Only steps to the beach via our private walkway pass our complex pool. This tastefully decorated, freshly painted, keyless entry unit boosts amazing full panoramic views of the ocean, fully equipped kitchen with large island and comes with many new furnishings, all new Egyptian cotton bed and bath linens, new comforters, blankets and pillows. Sorry but pets, golf carts, RV’s and trailers are prohibited.

Oceanfront Duplex~ linens included!

2 bdrm, 2 1/2 bth oceanfront duplex with 3 pools and tennis courts! Bed and Bath linens included! Private driveway for Golf cart rental permitted. Sorry, strict no pet policy. Sat -Sat weekly rentals in summer season. PLEASE NOTE: All three pools are for our guests to use and are maintained thru the HOA and we do not have any control over exactly when they open (Usually April 1st ) or if any of them closes for any reason. No refunds will be given if any of the pools are closed temporarily.

5 o’clock Always

This stunning 3-bedroom is an oasis of luxury and relaxation. This retreat boasts a blend of modern comfort and coastal charm. Nestled in a central location, it offers the perfect balance between convenience and tranquility. Immerse yourself in the serenity of the saltwater pool. After a leisurely swim, you'll find the allure of the nearby beach irresistible, just a 2.5 block stroll away. The interior unfolds in tasteful decor, creating an atmosphere you’ll never want to leave.

Private Heated Pool | 4 Min to Beach | King Beds

Happy Hour at OKI by Mountain to Waves – Just a 4-min verified walk to the beach! ✔ 4-minute walk to beach access ✔ Private heated pool ✔ Fully fenced backyard (perfect for pets) ✔ outdoor dining under a pergola, and a fire pit (wood provided). ✔ Arcade + air hockey for family fun ✔ Fully stocked kitchen for home-cooked meals ✔ Relax in 2 king bedrooms, including a spa-style primary bath with rain shower. ✔ Beach chairs, wagon & essentials included ✔ Quiet family neighborho

Luxury Beach House w/ Pool & Hot Tub - Sleeps 12

Welcome to this stunning beach getaway! This brand-new, modern home combines comfort, fun, and convenience for the ultimate coastal retreat. Designed with families and groups in mind, the house comfortably sleeps up to 12 guests across spacious bedrooms with plenty of room to relax after a day in the sun. Step inside, and you’ll find a bright, open layout with stylish finishes and all the modern touches you’d expect in a luxury beach house. Brand new hot tub as well!

The Coastal Coconut: Beautiful Ocean View Condo

This spectacular ocean view condo with top notch renovations is just steps from the beach. Be swept away by the view of the rolling waves, whitecaps, and the OKI Pier as you relax and enjoy a beverage on the balcony. You will also be treated to a breathtaking sunset as the colors change each minute across the sky. Retire to the living room and rest your tired feet on a comfy sectional sofa as you interact with others in an aesthetically pleasing open floorplan setting.

Luxury Family Retreat | Arcade | Pets Welcome

NEW POOL HEATER AND CHILLER! Step into your brand-new coastal getaway! This expansive 7-bedroom home with 10 beds and 6.5 bathrooms is ideal for large families and group stays. Enjoy quick beach access, a private pool with heater and chiller for all-season comfort, and an outdoor shower after sunny beach days. Inside, unwind with ping pong, foosball, and arcade games. Thoughtfully designed for babies, kids, and dogs—perfect for making lasting beachside memories.

OIB Oceanfront 3 Bd, 2 Bth with linens!

Beautifully decorated beach themed OSW1 complex top floor keyless entry 3 bdrm, 2 bath oceanfront condo with panoramic views of the sea. This unit boosts a fully stocked kitchen, ready made beds with all linens and two baths with a set of towels per guest. New furniture, two large wall mounted TV’s, beach chairs, umbrella and beach towels are available for your convenience. Sat-Sat weekly rentals in season. No golf carts or trailers allowed. No pets allowed.

3 Little Birds • Beach + Pool

Unwind at 3 Little Birds—a coastal retreat just 5 mins from the beach and near the Intracoastal! This 3BR home features a private pool, tiki bar, fenced yard, screened patio, ping pong, grill, and an outdoor shower. Sleep easy with a king bed and walk-in shower in the master, plus 2 guest rooms. Includes washer/dryer, beach gear, and a half bath by the pool. Book your stay today—because every little thing is gonna be alright!