
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.

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.

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.

Panoramic Ocean Views, 2 Pools, Huge Deck, Golf!
Your vacation awaits at this tranquil retreat on Caswell Beach, Oak Island! Embrace the serenity as you wake up to breathtaking ocean views and the gentle lull of waves. Recently renovated, this 3BR/2BA condo boasts an expansive deck, offering ample room for your family to relax and recharge. Just steps away lies a secluded beach with shallow waters, perfect for endless playtime with the kids. Take advantage of the nearby community pools and adjacent golf course for even more enjoyment

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

Wonderful New Home w/ Saltwater Pool, Dog Friendly

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

Pool*Sleeps 10*4BR/3BA*Family Friendly*54th St

Shake it Off

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

Cool beach house w/ Pool

Heated Pool + Tiki Bar | Dog Friendly

Beautiful home with pool & marsh view ‘Breakaway’
Condo rentals with a pool

Ocean Cove Mermaid

Oceanfront Third Floor Condo w/pool (Riggings E-3)

SoulSide - Oceanfront Condo in Wrightsville Beach

Ocean front, 1 bedroom condo w/ pool, Reef Relief

Dual master, end unit condo with amazing views

OIB~Oceanfront Condo 3 Bd/2Bath, linens included!

No Cleaning Fee - Condo With Waterfront Pool/Beach

Lovely 1 Bedroom Condo with Pool Ocean Isle Beach
Other vacation rentals with a pool

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

Coastal Serenity

Holden Beach Oceanfront Luxury w/ Heated Pool

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

Bright & Beachy Oceanfront Condo: Linens included!

Living the Coastal Dream in Southport

Sun-drenched beach condo with a view!

Oak Island Condo - 5 min walk to beach
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$34,323 GYD | G$32,440 GYD | G$39,556 GYD | G$46,671 GYD | G$56,508 GYD | G$65,298 GYD | G$62,787 GYD | G$60,275 GYD | G$50,857 GYD | G$40,602 GYD | G$39,556 GYD | G$46,671 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$12,557 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
Destinations to explore
- Augusta Vacation rentals
- Western North Carolina Vacation rentals
- Myrtle Beach Vacation rentals
- Charleston Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Savannah Vacation rentals
- Hilton Head Island Vacation rentals
- Cape Fear River Vacation rentals
- James River Vacation rentals
- North Myrtle Beach Vacation rentals
- Asheville Vacation rentals
- Rentals with a fireplace Oak Island
- Fitness-friendly rentals Oak Island
- Rentals with a washer and dryer Oak Island
- Rentals with beach access Oak Island
- Beach condo rentals Oak Island
- Bungalow rentals Oak Island
- Villa rentals Oak Island
- Pet-friendly rentals Oak Island
- Hotel rooms Oak Island
- Beach house rentals Oak Island
- Rentals with a hot tub Oak Island
- Rentals with a patio Oak Island
- Rentals with an EV charger Oak Island
- Private suite rentals Oak Island
- Condo rentals Oak Island
- House rentals Oak Island
- Rentals with a fire pit Oak Island
- Family-friendly rentals Oak Island
- Apartment rentals Oak Island
- Beachfront rentals Oak Island
- Waterfront rentals Oak Island
- Rentals with outdoor seating Oak Island
- Rentals with a kayak Oak Island
- Rentals with pools Brunswick County
- Rentals with pools North Carolina
- Rentals with pools United States
- 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
- Myrtle Beach State Park
- Myrtle Beach SkyWheel
- Wrightsville Beach
- Surf City Pier
- Cherry Grove Fishing Pier
- Ripley's Aquarium of Myrtle Beach
- Myrtle Waves Water Park
- Jungle Rapids Family Fun Park
- Carolina Beach Lake Park
- Broadway at the Beach
- Airlie Gardens
- Lakewood Camping Resort
- University of North Carolina Wilmington
- Bird Island
- WonderWorks Myrtle Beach




