
Vacation 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.

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.

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. Sunday -Sunday weekly rental in summer season with the exception of July 11th, 12th weekend is available.

Private Heated Pool, Steps to Beach, Pets OK
Happy Hour at OKI by Hearth and Horizon Family Getaways – Just a 4-min verified walk to the beach! 1. Enjoy a private pool with fountains, 2. outdoor dining under a pergola, and a fire pit (wood provided). 3. Game room features air hockey, arcade (Mortal Kombat), kids’ books & toys. 4. Relax in 2 king bedrooms, including a spa-style primary bath with rain shower. Perfect for families looking for beach fun and cozy comfort! 5. Fenced backyard for your fur baby to run around!

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!

Making Waves-Scenic Getaway- Heated 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.

Oceanfront | Breathtaking Sunrise l Pool
Peach on the Beach is a modern & newly renovated one bedroom condo, with a spacious open living room/kitchen area. This is a corner unit, which provides breathtaking views with access to a large covered oceanfront deck. Just a 2 minute walk to the beach. Perfect location for the sunrise and sunset lovers! Enjoy the ocean sunrise from the deck or beach & directly accross the street at the Fort Fisher Air Force Recreational Center are the best sunsets on the river.

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

⭐️100% Family-Friendly Getaway!⭐️Book Now⭐️

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

Family Beach Escape 2nd Row Pool Elevator & Views

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

Maggie’s Oasis

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

5 o’clock Always

Swimming Pool, Elevator, Fire Pit, Walk to Beach
Condo rentals with a pool

The Gathering Place Condo w/ Ocean Views & Pool

OCEANFRONT & ON the BOARDWALK! Unbelievable VIEWS

Coastal Escapes Luxury 3 bdrm Oceanfront Condo

Best Location! Beachfront-Boardwalk-Pool-Balcony

*Renovated* Top Floor Oceanfront Condo w/ Pool

OCEANFRONT PARADISE WITH SPECTACULAR OCEAN VIEWS

No Cleaning Fee - Condo With Waterfront Pool/Beach

Just Steps To The Beach
Other vacation rentals with a pool

Luxury: Beach, Pool, Golf, Boat Ramp, Pickle Ball

“Oki Ducki”4bdrm cottage, Private Pool & Golf Cart

OIB~Oceanfront Condo 3 BD/2BA, Linens Included!

St. James Condo | Wooded Views | Quiet & Peaceful

Suite Life in St. James

The Villas at Oak Island #7, Pool & Ocean Views

Oceanview Condo, Pool, 2 min walk to the sand

Wave On Wave
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 € 43 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 & 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
4.6 Average rating
Oak Island stays receive an average rating of 4.6 out of 5 from guests
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