Vacation rentals with a pool in Oak Island

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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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Guest favourite
The open-concept living space features a well-equipped kitchen with white cabinetry and modern appliances. A dining area with two wooden chairs is visible, complemented by vibrant wall decor displaying the phrase 'BEACH PLEASE,' creating a welcoming atmosphere for guests.
Condo in Oak Island
4.86 out of 5 average rating, 65 reviews

BEACH PLEASE │ 2BR/2BA w/ 2 K in the heart of OKI!

Feel the sand between your toes with a 2 minute walk to the beautiful beaches of OKI. Beach Please is a spacious 2BR/2BA condo with a comfortably furnished floor plan perfect for a family vacation or couple’s retreat. Boasting a fully equipped kitchen, 2 king beds + twin bunk beds this condo provides a cozy spot for renters looking to unwind and relax. Centrally located in the heart of Oak Island-steps away from the pool, beach, grocery store, restaurants, shopping, ice cream and so much more!

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, 204 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.

Guest favourite
Condo in Oak Island
4.87 out of 5 average rating, 23 reviews

Blue Wolf Retreat! Walk to beach/shops/groceries!

Just ONE Block from the beach, your family will be close to everything when you stay at the centrally-located Ocean Walk neighborhood! We are located steps from beach access and the facility has a HUGE pool! Right in the mix, you will never have to stress about parking, being walkable to the beach, groceries, restaurants, and more! This two bedroom unit is spacious at nearly 1300sqft! Plenty of space and beds for you, friends, family and pets so that you enjoy an amazing coastal retreat!

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
4.99 out of 5 average rating, 209 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 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, 215 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, 172 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, 296 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
A clear blue pool is surrounded by a stone deck and lounge chairs, with palm trees visible in the background. The pool area is enclosed by a black fence, providing a sense of privacy. The sky is partly cloudy, offering a bright atmosphere.
Apartment in Oak Island
4.99 out of 5 average rating, 77 reviews

The Villas at Oak Island #1, 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.

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, 123 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
Apartment in Southport
5 out of 5 average rating, 10 reviews

Hidden Gem | Short Drive To Beach | Spacious

Top floor corner unit in a quiet condo building. 12 minutes from Southport and Oak Island. Comfortable and fully equipped. Take advantage of the buildings amenities including the pool with sun loungers, treed parks, and the scenic pier. Enjoy the waterfront restaurants in Southport or take a stroll on the beach at Oak Island. Marina and kayak launch are also available within the community. Just what you need for a relaxing stay in St. James!

Guest favourite
A living area is visible, featuring a comfortable sofa and a large TV mounted on the wall. Natural light floods in through sliding glass doors, providing a view of the ocean. A dining table is situated on a balcony, where outdoor seating can also be seen.
Apartment in Carolina Beach
4.97 out of 5 average rating, 125 reviews

Updated beachfront condo with stunning views!

Come relax at this peaceful beachfront oasis. This 1 bedroom, 1 bathroom condo is located in popular Sea Colony at Carolina Beach. An additional bunk and pull-out sofa make this the perfect spot for the whole family. Great location within walking distance to many local restaurants and shops. Located on the top floor with no neighbors above you make this unit very quiet and private. No elevator in this building.

Guest favourite
Home in Oak Island
4.94 out of 5 average rating, 96 reviews

Sip & Dip* Luxury Saltwater Pool*Huge Porch*Mural

Welcome to your private beach resort-room for two families to relax comfortably. Nestled in nature less than a mile from the beach, enjoy a standout 30×12 saltwater pool, 350-sq-ft screened porch, back dining deck, covered gas grill area, and a bonus TV & game room. Modern, clean, and designed for easy coastal living. Beach gear & linens included. Roku TVs in every bedroom.

Popular amenities for Oak Island rentals with a pool

When is the best time to visit Oak Island?

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Avg. price$277 CAD$277 CAD$378 CAD$310 CAD$376 CAD$434 CAD$417 CAD$401 CAD$338 CAD$270 CAD$263 CAD$310 CAD
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Quick stats about vacation rentals with a pool in Oak Island

  • Total vacation rentals

    Explore 640 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 6,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    580 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    640 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

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