
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.

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.

Oceanfront 2 BR/2.5 BA Condo
Come enjoy our townhome in the Oak Island Beach Villas #206 located on Caswell Beach! Lounge on the oceanside deck incorporated into the living room, or enjoy a private balcony off the main bedroom upstairs overlooking the Atlantic Ocean! Make the most amazing memories watching the dolphins, observing the sea turtles lay their eggs, and watching the most amazing sunsets/sunrises you'll ever see. This condo is right across from the golf course. This is by far the most beautiful beach ever!

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.

Best Location! Beachfront-Boardwalk-Pool-Balcony
Unbeatable location directly on the famous Carolina Beach Boardwalk! Step outside the door and you’re just seconds away from the beach and ocean, where you can enjoy swimming, sunbathing, and even spotting dolphins from the shoreline. The boardwalk itself is a hub of activity, with bars, restaurants, shops, and live music just steps away. Whether you’re in the mood for a casual meal, a fun night out, or exploring the local boutiques, you’ll find it all within walking distance.

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.

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.

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.

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.

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!

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!

No Cleaning Fee - Condo With Waterfront Pool/Beach
Visit the most adorable seaside village! Southport, with it's picturesque waterfront, fantastic restaurants, and adorable shops, has something for everyone. When you feel like staying closer to home, the pool will be calling your name for soaking in the sun while watching the ships sail by, and your private balcony is the perfect spot to sip a cup of coffee while watching the sunrise over the water.
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

Pool*Sleeps 10*4BR/3BA*Family Friendly*54th St

Sunny Daze | 3BR,2.5BA - Pool, Spa & Porch Living

Fox On The Beach - across from beach, heated pool

Beautiful home with pool & marsh view ‘Breakaway’

One block to the beach with POOL, golf cart opt.

Oak Island 2nd Row 5 BDR Beach Home w/Private Pool

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

Captain’s Watch Home
Condo rentals with a pool

The Tropical Palm-Ocean View, Pool, Heart of CB

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

The Sweet Spot II

Dual master, end unit condo with amazing views

Stones Throw to downtown Southport

Just Steps To The Beach

Escape to the Cape On the Gorgeous SPT Waterfront

No Cleaning Fee! New Condo w/ Waterfront Pool
Other vacation rentals with a pool

*Heated* Pool, Hot Tub & Dock, 3 min Walk to Beach

4bed- Family Fun: Game Room + Pool + BBQ + Hot Tub

Oceanfront balcony views | pool & beach access

The Coastal Hideaway at OIB

Ocean Front Paradise

Sea View Villa~Ocean Front~Newly Renovated~Pool

The Oak Tree Bungalow. Relaxed Island Living

Ohana Oasis | Ocean Views • Pool • Steps to Beach
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 CAD | $278 CAD | $379 CAD | $311 CAD | $377 CAD | $435 CAD | $418 CAD | $402 CAD | $339 CAD | $271 CAD | $264 CAD | $311 CAD |
| Avg. temp | 8 °C | 10 °C | 13 °C | 18 °C | 22 °C | 26 °C | 28 °C | 27 °C | 24 °C | 19 °C | 13 °C | 10 °C |
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 $84 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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- Myrtle Beach Boardwalk
- Barefoot Landing
- Carolina Beach Boardwalk
- Lakewood Camping Resort
- Wrightsville Beach, NC
- Barefoot Resort & Golf
- Cherry Grove Point
- Kure Beach Pier
- Wrightsville Beach
- Myrtle Beach State Park
- Cherry Grove Fishing Pier
- North Carolina Aquarium at Fort Fisher
- Surf City Pier
- Family Kingdom Amusement Park
- Broadway at the Beach
- Carolina Beach Lake Park
- Myrtle Beach SkyWheel
- North Myrtle Beach Park & Sports Complex
- University of North Carolina Wilmington
- Myrtle Waves Water Park
- Jungle Rapids Family Fun Park
- Carolina Beach State Park
- Ripley's Aquarium of Myrtle Beach
- Bird Island





