
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.

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!

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.

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.

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.

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 #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.

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.

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
House rentals with a pool

Cheerful 3 BR/2.5BA Family Home w/POOL, walk to ev

Cool beach house w/ Pool

Ocean Isle Retreat

Holden Beach Oceanfront Luxury w/ Heated Pool

Beautiful home with pool & marsh view ‘Breakaway’

5 o’clock Always

3 Putt Paradise

Boat Right Inn-Pool-Canal-Dock -Walk to the Beach!
Condo rentals with a pool

SoulSide - Oceanfront Condo in Wrightsville Beach

Ocean front, 1 bedroom condo w/ pool, Reef Relief

Dual master, end unit condo with amazing views

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

Stones Throw to downtown Southport

Lovely 1 Bedroom Condo with Pool Ocean Isle Beach

OCEAN SOUNDS - UNIT 2106 OCEAN DUNES

Escape to the Cape On the Gorgeous SPT Waterfront
Other vacation rentals with a pool

East End Cottage w/ Pool across street from Beach

Coastal Serenity

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

Condo steps to beach w/ pool. Dog friendly!

The Oak Tree Bungalow. Relaxed Island Living

Southport/Oak Island NC Home

Vacation Condo in Kure Beach! The Riggings I1

Scenic Caswell Beach!Clean+Convenient+Sleeps 8
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. 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 $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
- Augusta Vacation rentals
- Western North Carolina Vacation rentals
- Myrtle Beach Vacation rentals
- Charleston Vacation rentals
- Outer Banks Vacation rentals
- Charlotte Vacation rentals
- Hilton Head Island Vacation rentals
- Savannah Vacation rentals
- Cape Fear River Vacation rentals
- James River Vacation rentals
- North Myrtle Beach Vacation rentals
- Asheville Vacation rentals
- Beach house rentals Oak Island
- Rentals with a hot tub Oak Island
- Private suite rentals Oak Island
- Family-friendly rentals Oak Island
- Villa rentals Oak Island
- Rentals with a fireplace Oak Island
- Rentals with a kayak Oak Island
- Bungalow rentals Oak Island
- House rentals Oak Island
- Rentals with a firepit Oak Island
- Fitness-friendly rentals Oak Island
- Rentals with a washer and dryer Oak Island
- Rentals with beach access Oak Island
- Hotel rooms Oak Island
- Rentals with a patio Oak Island
- Rentals with outdoor seating Oak Island
- Condo rentals Oak Island
- Beachfront rentals Oak Island
- Waterfront rentals Oak Island
- Apartment rentals Oak Island
- Rentals with an EV charger Oak Island
- Pet-friendly rentals Oak Island
- Beach condo rentals Oak Island
- Rentals with pools Brunswick County
- Rentals with pools North Carolina
- Rentals with pools United States
- Myrtle Beach Boardwalk
- Barefoot Landing
- Carolina Beach Boardwalk
- Barefoot Resort & Golf
- Cherry Grove Point
- Kure Beach Pier
- Family Kingdom Amusement Park
- North Carolina Aquarium at Fort Fisher
- Wrightsville Beach
- Myrtle Beach State Park
- Myrtle Beach SkyWheel
- Cherry Grove Fishing Pier
- Surf City 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
- University of North Carolina Wilmington
- Wrightsville Beach, NC
- Lakewood Camping Resort
- Bird Island
- WonderWorks Myrtle Beach




