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

Total holiday rentals
Explore 680 holiday rentals in Oak Island

Nightly prices starting at
Oak Island holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 7,830 verified reviews to help you choose

Family-friendly holiday rentals
620 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
680 of Oak Island holiday rentals include wifi 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.

Sun-drenched beach condo with a view!
This beachfront property on Caswell Beach has one of the best views in the neighborhood. With three bedrooms, a spacious living room, renovated kitchen, and incredible light, it's truly the perfect vacation getaway - especially for groups of friends or family. Plus, there are two pools and the furniture is all new! The porch overlooks a nature preserve that not only acts as protection for our home against the elements but also as a home to many beautiful birds and deer you'll see during sunset.

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.

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 but pets, golf carts, RV’s and trailers are prohibited.

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.

5 o’clock Always
This stunning 3-bedroom is an oasis of luxury and relaxation. This retreat boasts a blend of modern comfort and coastal charm. Nestled in a central location, it offers the perfect balance between convenience and tranquility. Immerse yourself in the serenity of the saltwater pool. After a leisurely swim, you'll find the allure of the nearby beach irresistible, just a 2.5 block stroll away. The interior unfolds in tasteful decor, creating an atmosphere you’ll never want to leave.

Private Heated Pool | 4 Min to Beach | King Beds
Happy Hour at OKI by Mountain to Waves – 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 neighborho

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.

Pool, Spa, Fire Pit, & More at this OKI Escape!
BookSmart Properties presents: Coastal Cheers! This beautiful 3 bed/4 bath modern home is an easy walk from the beach. Enjoy incredible amenities, including a private pool, bbq grill, hot tub and deck seating. Inside, you’ll find a fully equipped kitchen, a cozy living area, and the convenience of an elevator. Discover nearby dining, shopping, and local attractions for a truly unforgettable coastal escape. Let's Coastal Cheers to your perfect vacation!

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.

Brand New w/ Pickleball Court & Heated Pool
This brand new, modern retreat is perfect for families seeking the ultimate escape. Enjoy ocean views from the 3rd row balcony and an expansive backyard with a private pickleball court, basketball goal, and stunning putting green. Relax by the refreshing pool surrounded by a beautifully turfed yard. The ultimate personal oasis you'll never want to leave! You won't find another backyard like it in Oak Island!
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

6BR Beachfront PrivPool (heat opt) HotTub Elevator

Oceanview House w/ Heated Pool — Walk to Pier

Sunny Daze | 3BR,2.5BA - Pool, Spa & Porch Living

Pool + Tiki Bar | Dog-Friendly OKI Beach Stay

Luxury Family Retreat | Arcade | Pets Welcome

3 Little Birds • Beach + Pool

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

Wave On Wave
Apartment rentals with a pool

Dual master, end unit condo with amazing views

OIB Oceanfront 3 Bd, 2 Bth with linens!

Stones Throw to downtown Southport

No Cleaning Fee! New Condo w/ Waterfront Pool

Finns Up- Dog Beach. Ocean Views. Clean & Comfy!

Ocean Cove Mermaid

No Cleaning Fee - Condo With Waterfront Pool/Beach

Oceanfront • Hot tub • Indoor Pool • Gym
Other holiday rentals with a pool

“Hang Ten”great location, pool & golfcart

Luxury Beach House w/ Pool & Hot Tub - Sleeps 12

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

Family Tides~Steps to Sand~Pool! Fun for All!

The Villas at Oak Island #1, Pool & Ocean Views

Steps to Beach | 5BR Retreat | Private Pool & Spa

Ocean Front Oak Island W Pool

Kid-Friendly Luxe, Kayak Our Dock, 2 Carts + Clubs
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 SGD | $253 SGD | $345 SGD | $380 SGD | $434 SGD | $538 SGD | $381 SGD | $366 SGD | $309 SGD | $246 SGD | $240 SGD | $283 SGD |
| 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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- Wrightsville Beach, NC
- Myrtle Beach Boardwalk
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