
Holiday rentals with a pool in Oak Island
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Top-rated rentals with a pool in Oak Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

5BR*Dbl. Master*1 Block to Beach* GAMEROOM* Yaupon
3-4 min. walk to the beach! 2 night min stay June 2024. 4 night min stay July-August 2024. Stay at our spacious "American Dreaming" cottage on Yaupon Beach/Oak Island and check off all of your vacation boxes! Sit by the firepit and listen to the sounds of the crashing waves, which are only 1 block away. Head down to the beach during the day and then cool off in our private stock tank pool while your kids play ping pong in the game room. Enjoy a short 10 minute drive down to historic Southport!

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.

SeaScape-Top Floor Ocean Views & Dips in the Pool!
You'll love sipping coffee and watching the sunset from the front deck of this beautiful and much sought after 3rd floor ocean view condo with private pool and a beach access is just a short walk away. This NON-SMOKING condo includes, 2 flat screen SmartTVs, cable, & private WiFi. The kitchen contains all essential tool, a limited amount of spices/staples. There's also a Keurig with a variety of coffee pods for your enjoyment. The queen sofa bed sleeps 2 comfortably. No pets are allowed.

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.

Cowabungalow - Luxury Condo
This custom LUXURIOUS 1-bedroom oceanfront sleeps 4 w/pull-out couch and is completely NEW inside. This unit is oceanfront, 2nd story w/elevator, covered parking in a gated parking lot, and a fully stocked kitchen, park the car & never have to drive during your stay! Right on the CB boardwalk w/ many choices for ocean view restaurants, etc. Pet friendly with an additional $60 cleaning fee per pet and early check-in and late check-out fee $150 for each request w/ 2-day notice.

The Coastal Coconut: Beautiful Ocean View Condo
This spectacular ocean view condo with top notch 2022 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.

Escape to the Cape On the Gorgeous SPT Waterfront
Located on the historic 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!

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.

Beachfront condo w/pool and great views
Kick back and relax in this calm, stylish space that is oceanfront. Enjoy coffee or cocktails in the deck while watching the waves. Just steps from the beach with a garage to store all your beach and ocean toys. Everything you need is provided for your stay. Enjoy the pool and grilling area in the complex. Free parking on site. The boardwalk is 1.5 miles away with plenty of things to do and places to eat but far enough away that you have peace and quiet.

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.

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

Newly renovated beachfront dog friendly w/ 4 bikes

Oceanfront|Stunning Views|1st FLR|Pool|Kure Beach

Wave On Wave

Pool | Views | Sleeps 8 | Linens | Yacht Drive

5 o’clock Always

Kid Friendly Luxe: Kayak Our Dock + 2 Carts, Clubs

Luxury Villa in Caribbean-Style Beach Resort

Private Heated Pool, Steps to Beach, Pets OK
Condo rentals with a pool

Ocean Cove Mermaid

☀️Oceanfront with Beach Access "Carla's Cabana"☀️

*Renovated* Top Floor Oceanfront Condo w/ Pool

Dual master, end unit condo with amazing views

Beach, Pools, Gym & Hot Tubs | Fun & Sun Villa

No Cleaning Fee - Condo With Waterfront Pool/Beach

Lovely 1 Bedroom Condo with Pool Ocean Isle Beach

Oceanfront Condo, Spacious Private Deck & Pool!
Other holiday rentals with a pool

Family Oasis with Private Hot Tub & game room

Oceanfront 2 BR/2.5 BA Condo

Amazing Location at Island Time is the Best Time!

1st fl Beachfront Condo w/pool

Sea-clusion: A ground floor beach front condo

Seaside Vista! Oceanfront condo w/ heated pool

The Oak Tree Bungalow. Relaxed Island Living

Bright & Beachy Oceanfront Condo: Linens included!
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $243 AUD | $229 AUD | $280 AUD | $330 AUD | $400 AUD | $462 AUD | $444 AUD | $426 AUD | $360 AUD | $259 AUD | $264 AUD | $235 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 |
Quick stats about holiday rentals with a pool in Oak Island

Total holiday rentals
Explore 600 holiday rentals in Oak Island

Nightly prices starting at
Oak Island holiday rentals start at $89 AUD per night before taxes and fees

Verified guest reviews
Over 6,540 verified reviews to help you choose

Family-friendly holiday rentals
510 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 180 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
600 of Oak Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Carolina Beach Boardwalk
- Myrtle Beach Boardwalk
- Barefoot Resort & Golf
- Wrightsville Beach, NC
- Cherry Grove Point
- Family Kingdom Amusement Park
- Freeman Park
- North Carolina Aquarium at Fort Fisher
- Myrtle Beach SkyWheel
- Wrightsville Beach
- Ripley's Aquarium of Myrtle Beach
- Surf City Pier
- Cherry Grove Fishing Pier
- Jungle Rapids Family Fun Park
- Myrtle Beach State Park
- Myrtle Waves Water Park
- Carolina Beach Lake Park
- Airlie Gardens
- Duplin Winery
- WonderWorks Myrtle Beach
- Oak Island Lighthouse
- University of North Carolina Wilmington
- Carolina Beach State Park
- Soundside Park




