Vacation 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

Family · Pool · Beach

Private Heated Pool | 4 Min to Beach | King Beds

Happy Hour at OKI by Hearth and Horizon Family Getaways – 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 neighborhood

Family · Location · Wifi

The Villas at Oak Island #3, 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. This unit is one of our pet free units.

Location · Family · Beach

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.

Location · Value · Nearby

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.

Value · Location · Cleanliness

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!

Family · Location · Check-in

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.

Location · Value · Checkout

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.

Value · Family · Laundry

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!

Family · Backyard · Cleanliness

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.

Value · Family · Cleanliness

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!

Location · Family · Bathroom

Brand New w/ Pickleball Court & Heated Pool

This brand new, modern retreat is perfect for families seeking the ultimate escape. Enjoy ocean views from the 3rd row balcony and an expansive backyard with a private pickleball court, basketball goal, and stunning putting green. Relax by the refreshing pool surrounded by a beautifully turfed yard. The ultimate personal oasis you'll never want to leave! You won't find another backyard like it in Oak Island!

Location · Family · Getting around