
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.

Ocean front, 1 bedroom condo w/ pool, Reef Relief
Enjoy a peaceful ocean front oasis with your family. Explore the coquina reef right out front, perfect for shell & shark tooth hunting. If you ever get tired of the ocean, bring the family over to the pool area. Kids will love our galley-style bunk beds, the bedroom has a queen bed & our couch folds out into another queen to fit adults. The Aquarium & brand new Fort Fisher Historical Site within walking distance, this is a great spot to relax without the craziness of being in the middle of town.

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.

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

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.

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!

Oceanfront Ocean Isle Beach Condo
My oceanfront unit is near the pier, beach shops, miniature golf, & the museum.You’ll love my place because the ocean view is amazing !There is a queen bedroom, bunk nook, queen sleeper sofa, a whirpool tub, & a washer/dryer in the unit.Unit faces the ocean and is located on the quiet end of the complex with a private deck & community pool.It is located at the center of island activities; you can walk to many shops.Bed linen/bath towels provided. Private beach access for guests.Pool open.

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.

Cheerful 3 BR/2.5BA Family Home w/POOL, walk to ev
This family-friendly home WITH A BRAND NEW DIY POOL/SPA is perfect for a family or 2, or group of friends. This quiet, but centrally-located spot is 0.7 miles (10 min. walk) to the beach, & just a few minutes walk to plenty restaurants, sweet treats, shops, grocery store, & more. You'll love having room for up to 12 guests w/3 bedrooms, 2.5 baths, a sunroom, fully-equipped kitchen, front & back porches, living room, laundry room, workspace, & huge garage w/games!

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.

Pool | Views | Sleeps 8 | Linens | Yacht Drive
Complete relaxation awaits! This beautifully appointed cottage sits across from the ICW with water views from the porch. Enjoy a private backyard oasis with pool, outdoor kitchen, and space to unwind. Inside, two king bedrooms and a queen-over-queen bunk room sleeps 8. Open layout, fully stocked kitchen, and minutes to the beach, dining, and attractions. LINENS INCLUDED, along with beach and pool towels. The perfect blend of comfort, fun, and convenience!

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.
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

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

“Oki Ducki”4bdrm cottage, Private Pool & Golf Cart

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

Shake it Off

Cool beach house w/ Pool

Mermaid Retreat* Private Pool* Pet Friendly

Fox On The Beach - across from beach, heated pool

Wave On Wave
Condo rentals with a pool

Beach vacation condo at Ft Fisher! Riggings L1

OIB~Oceanfront Condo 3 Bd/2Bath, linens included!

Oceanfront Duplex~ linens included!

Stones Throw to downtown Southport

No Cleaning Fee - Condo With Waterfront Pool/Beach

Just Steps To The Beach

Escape to the Cape On the Gorgeous SPT Waterfront

Fully Renovated Beautiful Oceanfront 2 BR Condo
Other vacation rentals with a pool

Oceanfront 2 BR/2.5 BA Condo

Family Tides, Beautiful views, Pool, Hot tub!

New kid friendly cottage w/pool & PrivateWalk

The Oak Tree Bungalow. Relaxed Island Living

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

Bright & Beachy Oceanfront Condo: Linens included!

Living the Coastal Dream in Southport

Dreams Do Come True, Oceanfront!
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $228 CAD | $216 CAD | $263 CAD | $311 CAD | $376 CAD | $435 CAD | $418 CAD | $401 CAD | $338 CAD | $270 CAD | $263 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 600 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 6,540 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
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- Myrtle Beach Boardwalk
- Barefoot Landing
- Carolina Beach Boardwalk
- Barefoot Resort & Golf
- Wrightsville Beach, NC
- Cherry Grove Point
- Kure Beach Pier
- Family Kingdom Amusement Park
- North Carolina Aquarium at Fort Fisher
- Myrtle Beach State Park
- Myrtle Beach SkyWheel
- Wrightsville Beach
- Surf City Pier
- Cherry Grove Fishing Pier
- Ripley's Aquarium of Myrtle Beach
- Myrtle Waves Water Park
- Jungle Rapids Family Fun Park
- Carolina Beach Lake Park
- Broadway at the Beach
- Airlie Gardens
- Lakewood Camping Resort
- University of North Carolina Wilmington
- Bird Island
- Carolina Beach State Park




