
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.

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.

Coastal Serenity
St. James Plantation / Harborwalk Condo With Pool And Private Beach Club! Enjoy our professionally decorated, immaculate three-bedroom, three full-bath condo. Located on the second floor, this condo features over 2000 sq ft of living space, Two private porches (one screened, one open air) steps away from the marina, dining, shopping, and entertainment. Only 15 minutes from the entrance, enjoy James by the Sea, an exclusive private beach club featuring a pool and restrooms, and showers.

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.

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!

WOW! Corner unit, jaw-dropping views, Avista#1614*
Why guests love our condo: *Our condo has it all! Two balconies to view panoramic views of the beach, one in the front of the condo to see the sunrise, one on the side to see city views of North Myrtle Beach and the sunset! Complete with high top table and chairs to admire the views! Corner unit. * Walking distance to Main Street, where there’s shops, restaurants, lounges with live entertainment and dancing. *North Myrtle Beach is quieter, safe and family friendly.

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.

Stones Throw to downtown Southport
Welcome to our gorgeous 1 bedroom/ 1bath home away from home! These roomy accommodations are just steps from the Southport Marina and in the heart of historic Southport. You have at your disposal boat parking, outdoor pool area, and walking access to Southport's many charms, such as fine dining and shopping. Bikes and beach chairs are in the closet in the covered parking. Your relaxation begins with easy self check-in and keyless entry! Enjoy your stay.

Hidden Gem | Short Drive To Beach | Spacious
Top floor corner unit in a quiet condo building. 12 minutes from Southport and Oak Island. Comfortable and fully equipped. Take advantage of the buildings amenities including the pool with sun loungers, treed parks, and the scenic pier. Enjoy the waterfront restaurants in Southport or take a stroll on the beach at Oak Island. Marina and kayak launch are also available within the community. Just what you need for a relaxing stay in St. James!

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

East End Cottage w/ Pool across street from Beach

Harbor Lights Resort | Waterfront, Pool & Dock!

NEW! Sunset Beach *Golf * Pools * Amenities Galore

Poolside Paradise w/ Tiki Bar + Dog Friendly

Brand New w/ Pickleball Court & Heated Pool

Ocean & Lake View |3BR |Steps to Beach & Boardwalk

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

Pool now open! Centrally located. Minutes to Beach
Apartment rentals with a pool

Ocean View! No Pet Fee! Come Relax @ The Escape CB

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

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

Sea-clusion: A ground floor beach front condo

2Br, Beach Access-Indoor Heated Pool!

No Cleaning Fee! New Condo w/ Waterfront Pool

Luxury King OceanFront Couple’s Suite

Southport’s Sweet Caroline
Other holiday rentals with a pool

La Vie en Sea - Luxe 2nd Row Condo with a Pool!

1 bedroom condo with pool- 15 minutes to beach

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

Oceanfront 2 BR/2.5 BA Condo

BEACH PLEASE │ 2BR/2BA w/ 2 K in the heart of OKI!

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

Ocean Front Paradise

Twisted Oak Tides - Oceanfront Escape
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €171 | €171 | €234 | €192 | €233 | €269 | €258 | €248 | €209 | €167 | €163 | €192 |
| 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 €52 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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