Holiday rentals with a pool in Oak Island

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Oak Island

  • Total holiday rentals

    Explore 680 holiday rentals in Oak Island

  • Nightly prices starting at

    Oak Island holiday rentals start at $89 SGD per night before taxes and fees

  • Verified guest reviews

    Over 7,830 verified reviews to help you choose

  • Family-friendly holiday rentals

    620 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    680 of Oak Island holiday 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

Top-rated rentals with a pool in Oak Island

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

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Top guest favourite
A spacious outdoor seating area is shown on a wooden deck, featuring a table with several chairs. A stunning sunset can be seen in the distance, casting warm colors across the sky. Lush greenery is present in the foreground and background.
Apartment in Oak Island
4.98 out of 5 average rating, 102 reviews

Sun-drenched beach condo with a view!

This beachfront property on Caswell Beach has one of the best views in the neighborhood. With three bedrooms, a spacious living room, renovated kitchen, and incredible light, it's truly the perfect vacation getaway - especially for groups of friends or family. Plus, there are two pools and the furniture is all new! The porch overlooks a nature preserve that not only acts as protection for our home against the elements but also as a home to many beautiful birds and deer you'll see during sunset.

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.
Apartment in Oak Island
4.99 out of 5 average rating, 218 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 showcases the oceanfront condo complex nestled near the beach, with a private walkway leading directly to the sandy shore. The blue ocean sparkles in the sunlight, with gentle waves lapping at the beach. Surrounding grassy areas and landscaped shrubs enhance the tranquil setting.
Flat in Ocean Isle Beach
4.98 out of 5 average rating, 132 reviews

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.

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.
Apartment in Ocean Isle Beach
4.99 out of 5 average rating, 222 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.

Guest favourite
A bright living room is furnished with a large blue sectional sofa, accented by a decorative pillow. Expansive windows frame views of the ocean and palm trees beyond. A ceiling fan circulates air while light spills into the space, creating a welcoming atmosphere.
Apartment in Oak Island
4.97 out of 5 average rating, 97 reviews

Panoramic Ocean Views, 2 Pools, Huge Deck, Golf!

Your vacation awaits at this tranquil retreat on Caswell Beach, Oak Island! Embrace the serenity as you wake up to breathtaking ocean views and the gentle lull of waves. Recently renovated, this 3BR/2BA condo boasts an expansive deck, offering ample room for your family to relax and recharge. Just steps away lies a secluded beach with shallow waters, perfect for endless playtime with the kids. Take advantage of the nearby community pools and adjacent golf course for even more enjoyment.

Top guest favourite
Home in Oak Island
4.9 out of 5 average rating, 61 reviews

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.

Guest favourite
Home in Oak Island
4.89 out of 5 average rating, 122 reviews

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

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.
Apartment in Oak Island
4.99 out of 5 average rating, 233 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, 183 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
Home in Oak Island
5.0 out of 5 average rating, 10 reviews

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!

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.
Apartment in Oak Island
4.95 out of 5 average rating, 128 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 backyard features a refreshing pool surrounded by lush, turfed areas. Lounge chairs and umbrellas provide shade, while a pickleball court and putting green are visible in the background. The space is enclosed by a white fence and framed by palm trees.
Home in Oak Island
4.99 out of 5 average rating, 79 reviews

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!

Popular amenities for Oak Island rentals with a pool

When is the best time to visit Oak Island?

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Avg. price$253 SGD$253 SGD$345 SGD$380 SGD$434 SGD$538 SGD$381 SGD$366 SGD$309 SGD$246 SGD$240 SGD$283 SGD
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