
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.

Surfrider Siesta -Indoor Pool -Hot Tub - Elevator
Relax with the family at this peaceful retreat. Surfrider Siesta is a very comfortable, family friendly place to stay. Fully equipped with all the cooking essentials, washer & dryer unit within condo, WiFi and cable. Private beach access is 100 steps from the front door. The complex has three outdoor pools which are seasonal and a recreational building with a heated indoor pool open all year round. It also has sauna, hot tub, gym and changing rooms. Sorry no pets allowed in rentals as per HOA.

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 Condo With Balcony and Pool
Welcome to our beachfront 1 bedroom condo at "The Riggings"! Enjoy the stunning ocean views from the comfort of your own private balcony. Inside, you'll find a cozy queen size bed, perfect for a romantic getaway or a solo retreat. We also have a twin size bunk bed and a pull out couch, making it perfect for families or groups of friends. Whether you're looking for a romantic escape, a family vacation, or a relaxing solo trip, our beachfront condo has everything you need for a perfect stay.

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.

Vista North (OCEAN+MARSH+POOL)
This is the perfect escape for those looking for waterfront cozy chic luxury. Just steps away from a pristine oceanfront preserve and biking distance to the boardwalk, restaurants and nightlife. Our recently updated stylish condo will give you an emersion of coastal beauty and an array of local attractions along with access to marsh side pool, bikes and grills. Start your day with a cup of coffee and an ocean sunrise and unwind with a glass of wine for an unmatched marsh view sunset.

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 Southport 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!

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 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.

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.

The Great Wave
Welcome to The Great Wave! This beautifully updated, 2 bed/2 bath 4th level condo (no elevator) has stunning ocean AND marina views and comes fully equipped with all of your basic essentials for a great vacation. Carolina Beach has activities for everyone, no matter the time of year, and this condo is located just a few feet away from it all! Includes two parking spots, seasonal pool, convenient beach access, and much more!
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

Family Beach Escape 2nd Row Pool Elevator & Views

Mermaid Retreat* Private Pool* Pet Friendly

Pool | Views | Sleeps 8 | Linens | Yacht Drive

5 o’clock Always

5BR*Dbl. Master*1 Block to Beach* GAMEROOM* Yaupon

Swimming Pool, Elevator, Fire Pit, Walk to Beach

Luxury Oceanview Home - New Construction

River Road Retreat - Heated Private Pool, Pond, Fi
Condo rentals with a pool

Beachfront Condo, Steps to the Beach

Morning brew with an ocean view

Oceanfront- panoramic Ocean Views w/pool(512)

Just Steps To The Beach

Oceanfront Condo, Spacious Private Deck & Pool!

Treetop Fairway Haven at Sea Trail

Beautiful Ocean Front Condo!

Southport’s Sweet Caroline
Other vacation rentals with a pool

Spacious | 12 min to Southport | Private Balcony

8-bedroom, 8-bathroom with Elevator & Heated Pool

Shake it Off

Oceanfront Gem: Balcony, Views, Beach Access, Pool

St James - King Bed & Porch (No Cleaning Fee)

Private Heated Pool, Tiki Hut- 10min walk to beach

1st fl Beachfront Condo w/pool

New, Oceanfront, 50 Steps to the Sand, Pool, Views
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $230 CAD | $217 CAD | $265 CAD | $313 CAD | $379 CAD | $438 CAD | $421 CAD | $404 CAD | $341 CAD | $245 CAD | $250 CAD | $223 CAD |
| 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 $70 CAD per night before taxes and fees

Verified guest reviews
Over 6,590 verified reviews to help you choose

Family-friendly vacation rentals
530 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 180 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wifi availability
600 of Oak Island vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oak Island rentals

4.6 Average rating
Oak Island stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Western North Carolina Vacation rentals
- Myrtle Beach Vacation rentals
- Charleston Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Cape Fear River Vacation rentals
- Savannah Vacation rentals
- Hilton Head Island Vacation rentals
- James River Vacation rentals
- Asheville Vacation rentals
- North Myrtle Beach Vacation rentals
- Virginia Beach Vacation rentals
- Fitness-friendly rentals Oak Island
- Rentals with a washer and dryer Oak Island
- Villa rentals Oak Island
- Rentals with a fireplace Oak Island
- Bungalow rentals Oak Island
- Apartment rentals Oak Island
- Beach condo rentals Oak Island
- Pet-friendly rentals Oak Island
- Rentals with a firepit Oak Island
- Beach house rentals Oak Island
- Beachfront rentals Oak Island
- House rentals Oak Island
- Rentals with a kayak Oak Island
- Rentals with a hot tub Oak Island
- Hotel rooms Oak Island
- Rentals with beach access Oak Island
- Waterfront rentals Oak Island
- Rentals with a patio Oak Island
- Private suite rentals Oak Island
- Rentals with outdoor seating Oak Island
- Rentals with an EV charger Oak Island
- Family-friendly rentals Oak Island
- Condo rentals Oak Island
- Rentals with pools Brunswick County
- Rentals with pools North Carolina
- Rentals with pools United States
- Myrtle Beach Boardwalk
- Barefoot Resort & Golf
- South Beach
- Cherry Grove Point
- Family Kingdom Amusement Park
- Dunes Golf and Beach Club
- Futch Beach
- Myrtle Beach SkyWheel
- Wrightsville Beach
- North Carolina Aquarium at Fort Fisher
- Surf City Pier
- Ripley's Aquarium of Myrtle Beach
- Cherry Grove Fishing Pier
- Seahorse Public Beach Access
- Jungle Rapids Family Fun Park
- Arrowhead Country Club
- Myrtle Waves Water Park
- Salt Marsh Public Beach Access
- Myrtle Beach State Park
- Carolina Beach Lake Park
- Airlie Gardens
- Tidewater Golf Club
- The Pavilion Park
- Long Beach




