
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 $99 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
680 of Oak Island holiday rentals include Wi-Fi 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.

Coastal Retreat w/ Private Pool | Golf Cart
Inside, the home features a bright, coastal-inspired design with inviting living spaces that make it easy to gather and unwind. The layout offers flexibility for a variety of group types, including a unique downstairs suite complete with a queen Murphy bed, private fridge, mini dishwasher, and microwave—creating the perfect semi-private space for guests who want their own retreat, whether it's extended family, teens, or another couple. Step outside and you’ll find where Bryd's Nest truly shines. The backyard has been transformed into a private oasis, complete with a sparkling pool, lush palm trees, and low-maintenance turf that keeps everything looking pristine year-round. The outdoor living area is built for entertaining, featuring comfortable seating, a firepit, and a large outdoor TV—ideal for game days, movie nights, or simply relaxing after a day at the beach. To make getting around effortless, the home includes a 4-seater golf cart, so you can cruise to the beach, local shops, or grab a bite without ever needing to move your car. Guests will also appreciate the included beach gear—chairs, and more—making beach days easy and enjoyable from the moment you arrive. Whether you’re lounging by the pool, enjoying evenings under the lights, or exploring everything Oak Island has to offer, Bryd's Nest delivers a fun, comfortable, and memorable coastal experience you’ll want to return to again and again. ***PLEASE NOTE THERE IS AN EXTERNAL CAMERA UNDER THE DECK VIEWING DRIVEWAY ONLY. USED DURING VACANCY AND EMERGENCY ⭐ Highlights - 4 Bedrooms | 3 Bathrooms - Private backyard oasis with pool, palm trees & turf - Outdoor living area with seating, firepit & large TV - 4-seater golf cart included - Unique downstairs suite with queen Murphy bed + kitchenette (fridge, mini dishwasher, microwave) - Beach gear included, drip coffee pot - Bright, stylish coastal interior design - Ideal for families, couples, and group getaways - Easy access to beach, dining, and local attractions .6 miles from beach 14 min walk or 3 minute drive

Private Pool Oasis I Hot Tub I Free Golf Cart!
Welcome to Beech2Beach, your ultimate coastal escape tucked away on the peaceful west end of Oak Island, NC. This charming 3-bedroom, 2-bath home is designed for relaxation, comfort, and making memories—with space to accommodate up to 8 guests with ease. From the moment you arrive, you’ll feel the shift into vacation mode. Surrounded by quiet streets and coastal breezes, this home offers the perfect balance of privacy and convenience—just a short ride to the beach, local dining, and island favo

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.

The Black Pearl
Rooftop Deck, Ocean Views, & Backyard Oasis in OKI This modern OKI gem is only steps from the beach & boasts incredible amenities. Enjoy the best views from the rooftop deck, a unique and luxurious place to relax with a drink & the sounds of the sea. The contemporary interior offers stylish furnishings and decor, making the kitchen & living area as sleek as they are functional. You will sleep soundly in the comfortable bedrooms after a day at the beach or in the backyard pool. Book asap!

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.

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!

Sand Surf & Sunset Ocean View Condo - 2 Bed 2 Baths
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.

Pool Home Dog Friendly Steps to Beach Sleeps 8
Bring the whole family, including the pups and enjoy this spacious 3BR/2BA beach retreat just steps from the sand! Sleeping up to 8 guests, this inviting home features a private pool, fenced backyard, and plenty of room to relax after a day at the beach. Perfect for families, friends, and furry companions looking for the ideal Oak Island getaway with comfort, convenience, and coastal charm.Reconnect with loved ones in this family-friendly place.

3 Little Birds • Beach + Pool
Unwind at 3 Little Birds—a coastal retreat just 5 mins from the beach and near the Intracoastal! This 3BR home features a private pool, tiki bar, fenced yard, screened patio, ping pong, grill, and an outdoor shower. Sleep easy with a king bed and walk-in shower in the master, plus 2 guest rooms. Includes washer/dryer, beach gear, and a half bath by the pool. Book your stay today—because every little thing is gonna be alright!
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

Family Tides, Beautiful views, Pool, Hot tub!

Ocean Front Paradise

Steps to Beach | 5BR Retreat | Private Pool & Spa

Poolside Paradise w/ Tiki Bar + Dog Friendly

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

“Hang Ten”great location, pool & golfcart

Oceanview House w/ Heated Pool — Walk to Pier

Mermaid You Look! Pool, spa, Ocean & Sunset Views
Condo rentals with a pool

Ocean Cove Mermaid

Beachfront Condo, Steps to the Beach

Ocean Front Condo at O.I.B. Come sea for yourself!

Oceanfront Third Floor Condo w/pool (Riggings E-3)

Dual master, end unit condo with amazing views

Stones Throw to downtown Southport

No Cleaning Fee - Condo With Waterfront Pool/Beach

Surf Shack! Carolina Beach Amazing Location!
Other holiday rentals with a pool

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

Coastal Serenity

Ocean Front Oak Island W Pool

Condo retreat by the beach

Luxury Oceanfront Penthouse Condo with Pool

Coastal Cove Hideaway

5 o’clock Always

Private POOL, hot tub, movie theater AND fire pit!
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $282 AUD | $282 AUD | $385 AUD | $424 AUD | $485 AUD | $601 AUD | $425 AUD | $408 AUD | $344 AUD | $275 AUD | $268 AUD | $316 AUD |
| 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 |
Destinations to explore
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Savannah Holiday rentals
- Charleston Holiday rentals
- Hilton Head Island Holiday rentals
- North Myrtle Beach Holiday rentals
- Virginia Beach Holiday rentals
- Asheville Holiday rentals
- Raleigh Holiday rentals
- Wilmington Holiday rentals
- Richmond Holiday rentals
- Outer Banks Holiday rentals
- Villa rentals Oak Island
- Beach condo rentals Oak Island
- Beach house rentals Oak Island
- Pet-friendly rentals Oak Island
- Family-friendly rentals Oak Island
- Apartment rentals Oak Island
- Hotel rooms Oak Island
- Beachfront rentals Oak Island
- House rentals Oak Island
- Condo rentals Oak Island
- Rentals with beach access Oak Island
- Waterfront rentals Oak Island
- Rentals with a hot tub Oak Island
- Rentals with a kayak Oak Island
- Private suite rentals Oak Island
- Rentals with pools Brunswick County
- Rentals with pools North Carolina
- Rentals with pools United States
- Wrightsville Beach, NC
- Myrtle Beach Boardwalk
- Carolina Beach Boardwalk
- Barefoot Resort & Golf
- Barefoot Landing
- Cherry Grove Point
- Kure Beach Pier
- Broadway at the Beach
- Myrtle Beach State Park
- Wrightsville Beach
- North Carolina Aquarium at Fort Fisher
- Cherry Grove Fishing Pier
- University of North Carolina Wilmington
- Surf City Pier
- Carolina Beach Lake Park
- Myrtle Beach SkyWheel
- Wilmington Riverwalk
- Carolina Beach State Park
- Myrtle Waves Water Park
- Bird Island
- Jungle Rapids Family Fun Park
- St James Properties
- Airlie Gardens
- Lakewood Camping Resort





