Vacation rentals with a pool in Oak Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Oak Island

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

%{current} / %{total}1 / 1
Guest favourite
Home in Oak Island
5 out of 5 average rating, 5 reviews

Family Tides~Steps to Sand~Pool! Fun for All!

"Family Tides" features modern furniture as the home was completely renovated in 2025. This home also has a private pool! You can visit "The Point", located on the island which is the perfect way to end your day by watching the sun fade over the glistening water! This home has ample living space both inside and out for a long day of fun in the sun! The public beach access is conveniently located across the street. The front porch offers a wide-open view of the ocean-it's like being on the ocean!

Guest favourite
A close-up of a large seashell resting on a railing, with a backdrop of colorful beach houses and a clear blue sky extending over the ocean in the distance.
Condo in Caswell Beach
5 out of 5 average rating, 22 reviews

Beach Bunker

Welcome to “Beach Bunker” a conveniently located 2nd floor ocean side condo on Caswell Beach. You will feel right at home the minute you walk in with its beachy & comfy vibe. Featuring 2 bedrooms, each with a closet, 2 full baths, fully equipped kitchen, open dining room living room combination plus plenty of outdoor space on the covered porch which boasts fabulous views. This condo is part of Oak Island Beach Villas which gives you private beach access, pool, grilling/picnic area & parking.

Guest favourite
Home in Oak Island
4.88 out of 5 average rating, 113 reviews

Private Heated Pool, 4 mins 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

Top guest favourite
A bright living area features a blue sofa and armchair, complemented by decorative pillows. A natural woven coffee table is placed on a soft blue and white area rug. Large glass doors open to a private balcony, allowing natural light and ocean views to fill the space.
Condo in Oak Island
4.99 out of 5 average rating, 194 reviews

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.

Top guest favourite
An aerial view captures the oceanfront duplex amidst nearby residences. The beach stretches along the horizon with golden sand and gentle waves, while a pool is visible on the property. The location is marked for clarity, emphasizing proximity to the shoreline.
Condo in Ocean Isle Beach
5 out of 5 average rating, 201 reviews

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.

Top guest favourite
A newly constructed two-story home is positioned on a level lot, featuring an expansive driveway and ground-level parking space. A wide staircase leads to the covered porch at the front of the house, while numerous windows allow for natural light. Lush landscaping surrounds the property.
Home in Oak Island
5 out of 5 average rating, 14 reviews

Pool Home in Oak Island

Forget your worries when you escape to this beautiful 3 bedroom Oak Island vacation home. Conveniently located within walking distance to the picturesque Oak Island beaches. Spend your days by the ocean or in the spacious backyard with private swimming pool. Located on a quiet street. Screened-in porch, smart tv's with streaming capabilities with your apps, wifi, keyless entry, fully stocked kitchen, outdoor shower, washer and dryer, games, puzzles and books for those rainy days.

Top guest favourite
A spacious living area features a comfortable sectional sofa facing a large window that offers ocean views. A ceiling fan adds to the airy atmosphere, while a wooden sideboard and round coffee table provide functional decor. Light enters from the sliding glass doors leading to the balcony.
Condo in Oak Island
4.99 out of 5 average rating, 207 reviews

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.

Top guest favourite
A serene backyard oasis features a heated saltwater pool, surrounded by lounge chairs and tropical landscaping. The two-story house is elevated, showcasing a spacious deck with shaded seating and stairs leading down to the pool area, inviting relaxation and enjoyment.
Home in Oak Island
4.96 out of 5 average rating, 165 reviews

Scenic Getaway with Pool & Hot Tub

Add some peace and tranquility to your trip...beautifully furnished on the inside, fully stocked house, with an oasis of a backyard - this is a home you'll want to visit again and again. With your own HEATED saltwater pool & hot tub, in a private backyard paradise...you may not ever want to leave the property. Minutes away from the beach, steps away from the Intracoastal Waterway, and one street over from the scenic beach walkway, this house will not disappoint.

Top guest favourite
A wooden boardwalk leads directly to the sandy beach, lined with lush greenery. The calm ocean stretches into the distance, showcasing a serene blue hue under a clear sky. Gentle waves meet the shore, creating a peaceful coastal scene.
Condo in Ocean Isle Beach
4.98 out of 5 average rating, 281 reviews

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.

Top guest favourite
An outdoor pool is surrounded by a spacious deck with several lounge chairs arranged for relaxation. Lush palm trees are visible in the background, complementing the serene pool atmosphere under a clear sky.
Apartment in Oak Island
4.98 out of 5 average rating, 44 reviews

The Villas at Oak Island #4, 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.

Top guest favourite
Two blue wine glasses are positioned alongside a bottle of Clos du Bois wine on a table, with an expansive view of the ocean and shoreline in the background. The light reflects off the water, creating a serene atmosphere.
Condo in Oak Island
4.96 out of 5 average rating, 119 reviews

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

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.

Top guest favourite
A private pool area features a rectangular inground pool surrounded by a spacious deck. A small plant stands in a pot, adding greenery to the space. Sunlight reflects off the water, and comfortable outdoor seating is arranged close to the screened porch.
Home in Oak Island
4.97 out of 5 average rating, 35 reviews

Beach Cottage Getaway with a private pool!

Relax with the whole family at our beach cottage - enjoy a short 1/2 mile walk to the beach or the intercoastal or enjoy the private new inground pool with loads of decking, seating for the whole family and a screened in porch! Lots of room to spread out and great outdoor entertainment area with a fire pit. Large living room, dining room and kitchen and a workspace as well. Perfect spot to enjoy all that Oak Island has to offer!

Popular amenities for Oak Island rentals with a pool

When is the best time to visit Oak Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$227 CAD$215 CAD$262 CAD$309 CAD$374 CAD$432 CAD$415 CAD$399 CAD$336 CAD$269 CAD$262 CAD$309 CAD
Avg. temp8 °C10 °C13 °C18 °C22 °C26 °C28 °C27 °C24 °C19 °C13 °C10 °C

Quick stats about vacation rentals with a pool in Oak Island

  • Total vacation rentals

    Explore 600 vacation rentals in Oak Island

  • Nightly prices starting at

    Oak Island vacation rentals start at $83 CAD per night before taxes and fees

  • Verified guest reviews

    Over 6,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    510 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 180 rentals that welcome pets

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wifi availability

    600 of Oak Island vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oak Island rentals

  • 4.7 Average rating

    Oak Island stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore