
Holiday 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.

Sun-drenched beach condo with a view!
This beachfront property on Caswell Beach has one of the best views in the neighborhood. With three bedrooms, a spacious living room, renovated kitchen, and incredible light, it's truly the perfect vacation getaway - especially for groups of friends or family. Plus, there are two pools and the furniture is all new! The porch overlooks a nature preserve that not only acts as protection for our home against the elements but also as a home to many beautiful birds and deer you'll see during sunset.

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.

Luxury Oceanview Home - Steps to Beach
Indulge in the luxury of beachside living at Casa Allora, a stunning Oak Island Beach House. This exquisite newly built 5-bedroom, 3.5-bathroom retreat comfortably accommodates 10 guests. Revel in modern comforts with amenities like a private pool, patio, BBQ grill, 3 king bedrooms, and 2 oversized front decks. Whether you love a cup of coffee while watching the sunrise over the ocean or enjoying a glass of wine at sunset with the breeze in your hair, Casa Allora has it all!

Escape to the Cape On the Gorgeous SPT Waterfront
Located on the beautiful Southport Waterfront you'll enjoy a well-appointed gem located within the RiverHotel of Southport that includes a small balcony with views of the Cape Fear River, guest pool, and private beach exclusively for our guests. We also have a huge deck with lots of tables and chairs to enjoy the spectacular water views! Covered parking is available within steps of the elevator. Make your Southport vacation memorable! Escape to the Cape awaits you!

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 | 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

Ocean Front Paradise

Heated Pool + Tiki Bar | Dog Friendly

Southport/Oak Island NC Home

Beautiful home with pool & marsh view ‘Breakaway’

5 o’clock Always

Captain’s Watch Home

OG Paradise | Private Pool & Hot Tub | Luxe Oasis

Luxury Beach House w/ Pool & Hot Tub - Sleeps 12
Apartment rentals with a pool

Dual master, end unit condo with amazing views

Stones Throw to downtown Southport

No Cleaning Fee - Condo With Waterfront Pool/Beach

Just Steps To The Beach

Light-filled/Beach-Ocean views/Top floor condo

Fully Renovated Beautiful Oceanfront 2 BR Condo

Oceanfront | Breathtaking Sunrise l Pool

A Little Piece of Paradise at Ocean Isle Beach
Other holiday rentals with a pool

Hang Zen! This house has it all!

East End Cottage w/ Pool across street from Beach

Welcome to Blue Heaven OIB

Private Condo: Ocean + Pool Getaway for 8

Ocean Isle Retreat

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

The Oak Tree Bungalow. Relaxed Island Living

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 | £121 | £114 | £139 | £164 | £199 | £230 | £221 | £212 | £179 | £143 | £139 | £164 |
| 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 holiday rentals with a pool in Oak Island

Total holiday rentals
Explore 640 holiday rentals in Oak Island

Nightly prices starting at
Oak Island holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 6,810 verified reviews to help you choose

Family-friendly holiday rentals
580 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
640 of Oak Island holiday 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
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- Kure Beach Pier
- Family Kingdom Amusement Park
- North Carolina Aquarium at Fort Fisher
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