
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.

Oceanfront 1 bedroom condo with pool
Relax at our ocean front condo close to the best of Carolina Beach but far enough from the hustle to enjoy the quiet and amazing views! Walk south to enjoy shopping, restaurants, music and entertainment at our family friendly boardwalk. Or walk north to fish and grab a drink at the pier. Bring your bikes, golf cart, as well as beach and pool toys and store them in the unit’s garage. Pull out sofa bed in lvng room allows you to accommodate up to 4 guests. Come make memories at our beautiful CB.

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.

Coastal Retreat
Enjoy the Carolina Coast, hear the waves, feel the sun on your face, and soak it all in at this top floor flat with ocean views. Steps away from the North Pier, High Tide Lounge and Tiki Bar, Freeman Park, and great coffee at the North End Café. Relax with a glass of wine on the balcony as the sun goes down. The abundant wildlife and marsh views from the back balcony are stunning. Stroll along the beach or sun yourself by the pool and leave our quaint island home feeling refreshed.

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.

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.

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.

OIB~Oceanfront Condo 3 BD/2BA, Linens Included!
3 bd, 2BA Oceanfront Condo in the sought after less crowded West End of Ocean Isle Beach! Only steps to the beach via our private walkway pass our complex pool. This tastefully decorated, freshly painted, keyless entry unit boosts amazing full panoramic views of the ocean, fully equipped kitchen with large island and comes with many new furnishings, all new Egyptian cotton bed and bath linens, new comforters, blankets and pillows. Sorry no pets!

OIB~Oceanfront Condo 3 Bd/2Bath, linens included!
Oceanfront keyless entry condo with amazing full views off a spacious deck with a pool, and only steps to the beach. This beautifully decorated unit boosts a fully equipped kitchen with a large island, coffee bar, new bathrooms with luxury towels and ready made beds with Egyptian Cotton premium linens and bed quilts. Stackable washer/Dryer, living room has a 60 inch wall TV. Friday-Friday weekly rentals in summer season. Strict no pet policy.

Take a Break at Shore Break!
Wake up to ocean views—and often dolphins 🐬—in this first-floor, oceanfront one-bedroom condo with the best seat in the house. Enjoy a king bed, fully stocked kitchen with granite counters, and stylish new furnishings. Relax on the large deck with outdoor dining and sweeping ocean views. Resort-style pool, picnic area, WiFi, coffee, beach chairs, linens, free parking, and on-site laundry included for an easy, relaxing stay by the sea.

Ocean Cove Mermaid
This sweet OCEAN FRONT CONDO is in walking distance to everything Beach related. Restaurants, Fishing pier, and new recreation/park for all ages!! The unit is freshly remodeled. Adding a full bath making the unit have 2 full baths. 1 with tub. Bedroom with queen, Bunk area with a full and twin, pull out queen sleeper sofa, full kitchen, living room, dining area. Linens will be provided Off-season monthly rentals available!!
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

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

NEW! Oceanfront, Pool, Pickleball, Tiki Bar & More

Ocean View*Pool*Dog Friendly*Elevator*Location!

Winter Deals! Heated Pool & 0.5 mile to OKI Beach

The Oasis - Heated POOL - Tiki Bar - Beach Life!

5 o’clock Always

Home with Salt water pool and bamboo garden view

5BR*Dbl. Master*1 Block to Beach* GAMEROOM* Yaupon
Condo rentals with a pool

Beachfront Condo, Steps to the Beach

OCEANFRONT & ON the BOARDWALK! Unbelievable VIEWS

The Tropical Palm-Ocean View, Pool, Heart of CB

The Great Wave

Amazing Ocean Views!

Ocean View Condo | Walk to Tiki Bar & Beach

Oceanfront Condo, Spacious Private Deck & Pool!

Spectacular * Oceanfront Condo - Once Upon A Tide
Other vacation rentals with a pool

Sanctuary Condo in St.James

St. James Condo | Wooded Views | Quiet & Peaceful

Amazing Location at Island Time is the Best Time!

The Oak Tree Bungalow. Relaxed Island Living

Seaside Vista! Oceanfront condo w/ heated pool

Quiet Beach, Ocean View, Pool, Steps to Beach

Bright & Beachy Oceanfront Condo: Linens included!

Living the Coastal Dream in Southport
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$34,319 GYD | G$32,436 GYD | G$39,551 GYD | G$46,666 GYD | G$56,501 GYD | G$65,290 GYD | G$62,779 GYD | G$60,268 GYD | G$50,851 GYD | G$40,597 GYD | G$39,551 GYD | G$46,666 GYD |
| 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 G$12,556 GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 180 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
600 of Oak Island vacation 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
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- Carolina Beach Boardwalk
- Myrtle Beach Boardwalk
- Barefoot Resort & Golf
- Wrightsville Beach, NC
- Cherry Grove Point
- Family Kingdom Amusement Park
- North Carolina Aquarium at Fort Fisher
- Myrtle Beach SkyWheel
- Wrightsville Beach
- Cherry Grove Fishing Pier
- Surf City Pier
- Ripley's Aquarium of Myrtle Beach
- Myrtle Beach State Park
- Jungle Rapids Family Fun Park
- Carolina Beach Lake Park
- Myrtle Waves Water Park
- Airlie Gardens
- WonderWorks Myrtle Beach
- Oak Island Lighthouse
- Barefoot Landing
- Carolina Beach State Park
- Broadway at the Beach
- Bird Island
- University of North Carolina Wilmington




