Holiday rentals with a pool in Oak Island

Coastal Retreat w/ Private Pool | Golf Cart

Inside, the home features a bright, coastal-inspired design with inviting living spaces that make it easy to gather and unwind. The layout offers flexibility for a variety of group types, including a unique downstairs suite complete with a queen Murphy bed, private fridge, mini dishwasher, and microwave—creating the perfect semi-private space for guests who want their own retreat, whether it's extended family, teens, or another couple. Step outside and you’ll find where Bryd's Nest truly shines. The backyard has been transformed into a private oasis, complete with a sparkling pool, lush palm trees, and low-maintenance turf that keeps everything looking pristine year-round. The outdoor living area is built for entertaining, featuring comfortable seating, a firepit, and a large outdoor TV—ideal for game days, movie nights, or simply relaxing after a day at the beach. To make getting around effortless, the home includes a 4-seater golf cart, so you can cruise to the beach, local shops, or grab a bite without ever needing to move your car. Guests will also appreciate the included beach gear—chairs, and more—making beach days easy and enjoyable from the moment you arrive. Whether you’re lounging by the pool, enjoying evenings under the lights, or exploring everything Oak Island has to offer, Bryd's Nest delivers a fun, comfortable, and memorable coastal experience you’ll want to return to again and again. ***PLEASE NOTE THERE IS AN EXTERNAL CAMERA UNDER THE DECK VIEWING DRIVEWAY ONLY. USED DURING VACANCY AND EMERGENCY ⭐ Highlights - 4 Bedrooms | 3 Bathrooms - Private backyard oasis with pool, palm trees & turf - Outdoor living area with seating, firepit & large TV - 4-seater golf cart included - Unique downstairs suite with queen Murphy bed + kitchenette (fridge, mini dishwasher, microwave) - Beach gear included, drip coffee pot - Bright, stylish coastal interior design - Ideal for families, couples, and group getaways - Easy access to beach, dining, and local attractions .6 miles from beach 14 min walk or 3 minute drive

"Pearl on a Strand" 6Bd/4Ba w/ Pool, Opt Golf Cart

Just a brief stroll or golf cart ride to the beach, this spectacular home includes a heated pool and spa, and a Peloton! Accommodating 12 guests, the open floor plan features a stocked kitchen, dining room, living room, and eating space. The main floor includes 2 bedrooms, a 3/4 bath, and covered porches. Upstairs showcases 4 bedrooms, 3 baths, a laundry area, and 2 additional porches. **6-seat golf cart available for $85/day via property manager.** DUE TO SEVERE ALLERGIES, WE DO NOT ALLOW PETS.

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.

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.

The Black Pearl

Rooftop Deck, Ocean Views, & Backyard Oasis in OKI This modern OKI gem is only steps from the beach & boasts incredible amenities. Enjoy the best views from the rooftop deck, a unique and luxurious place to relax with a drink & the sounds of the sea. The contemporary interior offers stylish furnishings and decor, making the kitchen & living area as sleek as they are functional. You will sleep soundly in the comfortable bedrooms after a day at the beach or in the backyard pool. Book asap!

Oceanview House w/ Heated Pool — Walk to Pier

Indulge in the luxury of beachside living at Casa Allora, a stunning Oak Island Beach House. This exquisite newly built 5-bedroom, 3.5-bathroom retreat comfortably accommodates 11 guests. Revel in modern comforts with amenities like a private pool, BBQ grill, 3 king beds, 2 queen beds, 1 twin bunk and 2 oversized front porches. Whether you love watching the sunrise from the top porch or enjoy a glass of wine at sunset on the beach with the breeze in your hair, Casa Allora has it all!

Mermaid You Look! Pool, spa, Ocean & Sunset Views

**Must be 25 to book** New construction!! Wake up to the sounds of the waves crashing at this beautiful brand new 2nd row home. Direct beach access, beautiful ocean views from the double decker front porches & all the amenities you could ever imagine. Mermaid You Look has everything you need for the ultimate beach getaway. Our home is fully stocked with all the beach gear, paddle board, family games, baby gear, etc. After a long day at the beach relax in the private pool or hot tub.

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.

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

Gratitude is your perfect island escape, offering a private in-ground pool, golf cart access (available for an additional daily fee), and an easy, convenient location. Just 0.7 miles to the beach, with quick access to West End beaches and simple on/off island travel. This 3-bedroom, 2-bath home features two queen beds and one king bed, making it ideal for a relaxed, effortless beach stay—whether you’re soaking up the sun poolside or cruising to the shore.

The Villas at Oak Island #6, Pool & Ocean Views

This ocean view beach condo, part of The Villas at Oak Island, features 2 bedrooms, 1 full bathroom, and a fully equipped kitchen, along with a cozy combined living and dining area. Situated on the second row, it’s just a short walk to the beach, making it perfect for a family getaway. The Villas at Oak Island boasts a garden-style setting with an outdoor pool for your enjoyment. Linen, bath towels, and basic toiletries are provided for your convenience.

Pool, Spa, Fire Pit, & More at this OKI Escape!

BookSmart Properties presents: Coastal Cheers! This beautiful 3 bed/4 bath modern home is an easy walk from the beach. Enjoy incredible amenities, including a private pool, bbq grill, hot tub and deck seating. Inside, you’ll find a fully equipped kitchen, a cozy living area, and the convenience of an elevator. Discover nearby dining, shopping, and local attractions for a truly unforgettable coastal escape. Let's Coastal Cheers to your perfect vacation!

Sand Surf & Sunset Ocean View Condo - 2 Bed 2 Baths

Welcome to your perfect beachside retreat! This beautiful 2-Bedroom ocean-view condo in Caswell Beach, NC, offers breathtaking sunsets and panoramic ocean views right from your private covered decks - perfect for outdoor dining or unwinding to the sound of the waves. Just steps from the sand, this peaceful getaway is ideal for families or two couples looking to relax, recharge, and soak up the coastal charm. Walkable to restaurants, pier and golf.