
Vacation rentals with a pool in Oak Island
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Oak Island

Total vacation rentals
Explore 640 vacation rentals in Oak Island

Nightly prices starting at
Oak Island vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 6,810 verified reviews to help you choose

Family-friendly vacation rentals
580 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
640 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
Top-rated rentals with a pool in Oak Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

A Little Piece of Paradise at Ocean Isle Beach
OIB, “Gem of the Brunswick Islands” is the perfect place to relax, recreate & refresh. With its white sand, rolling waves and windswept marshes, OIB is 4.5 square miles of fabulous. The Odell Williamson Bridge connects the mainland to this piece of paradise. From there you'll see the island, the marsh savannahs below and the glistening ocean just over the horizon. Leave your worries and the hustle-bustle of the world behind - in just 0.3 miles, you'll be at the Parrot Suite, a Piece of Paradise.

Beach Bunker
Welcome to “Beach Bunker” a conveniently located 2nd floor ocean side condo on Caswell Beach. You will feel right at home the minute you walk in with its beachy & comfy vibe. Featuring 2 bedrooms, each with a closet, 2 full baths, fully equipped kitchen, open dining room living room combination plus plenty of outdoor space on the covered porch which boasts fabulous views. This condo is part of Oak Island Beach Villas which gives you private beach access, pool, grilling/picnic area & parking.

Private Heated Pool, 4 mins to Beach, King Beds
Happy Hour at OKI by Hearth and Horizon Family Getaways – Just a 4-min verified walk to the beach! ✔ 4-minute walk to beach access ✔ Private heated pool ✔ Fully fenced backyard (perfect for pets) ✔ outdoor dining under a pergola, and a fire pit (wood provided). ✔ Arcade + air hockey for family fun ✔ Fully stocked kitchen for home-cooked meals ✔ Relax in 2 king bedrooms, including a spa-style primary bath with rain shower. ✔ Beach chairs, wagon & essentials included ✔ Quiet family neighborhood

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.

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!

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.

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.

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

Luxury Oceanfront, Pickleball, Pool, & Tiki Bar!

Cheerful 3 BR/2.5BA Family Home w/POOL, walk to ev

Fabulous home with Pool and 8 Seater Golf Cart

Heated Pool + Tiki Bar | Dog Friendly

Southport/Oak Island NC Home

Beautiful home with pool & marsh view ‘Breakaway’

5 o’clock Always

You Me And The Sea: Across from the Beach!
Condo rentals with a pool

Coastal Escapes Luxury 3 bdrm Oceanfront Condo

Oceanfront End Unit Condo with Pool (Riggings D-2)

Dual master, end unit condo with amazing views

No Cleaning Fee - Condo With Waterfront Pool/Beach

Surf Shack! Carolina Beach Amazing Location!

Light-filled/Beach-Ocean views/Top floor condo

Spectacular Views! - Beach Front Condo!

No Cleaning Fee! New Condo w/ Waterfront Pool
Other vacation rentals with a pool

Oceanfront End-Unit 1st FLR w/pool Shamrock Sands

Ocean Isle Retreat

St. James Condo | Wooded Views | Quiet & Peaceful

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

The Oak Tree Bungalow. Relaxed Island Living

Condo steps to beach w/ pool. Dog friendly!

Bright & Beachy Oceanfront Condo: Linens included!

Dreams Do Come True, Oceanfront!
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ602 | ﺩ.ﺇ569 | ﺩ.ﺇ694 | ﺩ.ﺇ819 | ﺩ.ﺇ992 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,102 | ﺩ.ﺇ1,058 | ﺩ.ﺇ892 | ﺩ.ﺇ712 | ﺩ.ﺇ694 | ﺩ.ﺇ819 |
| 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 |
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- Myrtle Beach Boardwalk
- Barefoot Landing
- Carolina Beach Boardwalk
- Barefoot Resort & Golf
- Wrightsville Beach, NC
- Cherry Grove Point
- Kure Beach Pier
- Family Kingdom Amusement Park
- North Carolina Aquarium at Fort Fisher
- Wrightsville Beach
- Myrtle Beach State Park
- Myrtle Beach SkyWheel
- Cherry Grove Fishing Pier
- Surf City Pier
- Myrtle Waves Water Park
- Broadway at the Beach
- Ripley's Aquarium of Myrtle Beach
- Jungle Rapids Family Fun Park
- Carolina Beach Lake Park
- Lakewood Camping Resort
- Airlie Gardens
- University of North Carolina Wilmington
- Bird Island
- Carolina Beach State Park




