
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.

BEACH PLEASE │ 2BR/2BA w/ 2 K in the heart of OKI!
Feel the sand between your toes with a 2 minute walk to the beautiful beaches of OKI. Beach Please is a spacious 2BR/2BA condo with a comfortably furnished floor plan perfect for a family vacation or couple’s retreat. Boasting a fully equipped kitchen, 2 king beds + twin bunk beds this condo provides a cozy spot for renters looking to unwind and relax. Centrally located in the heart of Oak Island-steps away from the pool, beach, grocery store, restaurants, shopping, ice cream and so much 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.

Blue Wolf Retreat! Walk to beach/shops/groceries!
Just ONE Block from the beach, your family will be close to everything when you stay at the centrally-located Ocean Walk neighborhood! We are located steps from beach access and the facility has a HUGE pool! Right in the mix, you will never have to stress about parking, being walkable to the beach, groceries, restaurants, and more! This two bedroom unit is spacious at nearly 1300sqft! Plenty of space and beds for you, friends, family and pets so that you enjoy an amazing coastal retreat!

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.

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.

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.

The Villas at Oak Island #1, Pool & Ocean Views
This ocean view beach condo, part of The Villas at Oak Island, features 2 bedrooms, 1 full bathroom, and a fully equipped kitchen, along with a cozy combined living and dining area. Situated on the second row, it’s just a short walk to the beach, making it perfect for a family getaway. The Villas at Oak Island boasts a garden-style setting with an outdoor pool for your enjoyment. Linen, bath towels, and basic toiletries are provided for your convenience.

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.

Hidden Gem | Short Drive To Beach | Spacious
Top floor corner unit in a quiet condo building. 12 minutes from Southport and Oak Island. Comfortable and fully equipped. Take advantage of the buildings amenities including the pool with sun loungers, treed parks, and the scenic pier. Enjoy the waterfront restaurants in Southport or take a stroll on the beach at Oak Island. Marina and kayak launch are also available within the community. Just what you need for a relaxing stay in St. James!

Updated beachfront condo with stunning views!
Come relax at this peaceful beachfront oasis. This 1 bedroom, 1 bathroom condo is located in popular Sea Colony at Carolina Beach. An additional bunk and pull-out sofa make this the perfect spot for the whole family. Great location within walking distance to many local restaurants and shops. Located on the top floor with no neighbors above you make this unit very quiet and private. No elevator in this building.

Sip & Dip* Luxury Saltwater Pool*Huge Porch*Mural
Welcome to your private beach resort-room for two families to relax comfortably. Nestled in nature less than a mile from the beach, enjoy a standout 30×12 saltwater pool, 350-sq-ft screened porch, back dining deck, covered gas grill area, and a bonus TV & game room. Modern, clean, and designed for easy coastal living. Beach gear & linens included. Roku TVs in every bedroom.
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

Ocean Views I Sleeps 12 I Walk to Beach I Pool

Willow's Harbor

Gratitude 𓇼 Pool + Golf Cart + 0.7 mi to Beach

Home with Salt water pool and bamboo garden view

Heated POOL Elevator VIEWS West Beach Sleeps 12

Captain’s Watch Home

Newly renovated canal house with private pool

Private Heated Pool, 4 mins to Beach, King Beds
Condo rentals with a pool

Beachfront Condo, Steps to the Beach

Oceanfront Building-Boardwalk-Pool-Prime Location!

Oceanfront • Hot tub • Indoor Pool • Aquarium

The Tropical Palm-Ocean View, Pool, Heart of CB

Dual master, end unit condo with amazing views

Stones Throw to downtown Southport

Escape to the Cape On the Gorgeous SPT Waterfront

Sea the Lake ☼ Ocean & Lake Views ☼ Carolina Beach
Other vacation rentals with a pool

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

Flip Flop Inn

Oceanfront End Unit with Sunrise & Sunset Views

Top of Waves! Luxury oceanfront w/amazing views

Oceanfront balcony views | pool & beach access

Lovely 3 bedroom condo close to beach w/ pool

Beautiful home with pool & marsh view ‘Breakaway’

Ohana Oasis | Ocean Views • Pool • Steps 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 | $277 CAD | $277 CAD | $378 CAD | $310 CAD | $376 CAD | $434 CAD | $417 CAD | $401 CAD | $338 CAD | $270 CAD | $263 CAD | $310 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 640 vacation rentals in Oak Island

Nightly prices starting at
Oak Island vacation rentals start at $83 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
640 of Oak Island vacation 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
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- Myrtle Beach Boardwalk
- Barefoot Landing
- Carolina Beach Boardwalk
- Lakewood Camping Resort
- Wrightsville Beach, NC
- Barefoot Resort & Golf
- Cherry Grove Point
- Kure Beach Pier
- Wrightsville Beach
- Myrtle Beach State Park
- Cherry Grove Fishing Pier
- North Carolina Aquarium at Fort Fisher
- Surf City Pier
- Family Kingdom Amusement Park
- Carolina Beach Lake Park
- Broadway at the Beach
- Myrtle Beach SkyWheel
- North Myrtle Beach Park & Sports Complex
- University of North Carolina Wilmington
- Myrtle Waves Water Park
- Jungle Rapids Family Fun Park
- Carolina Beach State Park
- Ripley's Aquarium of Myrtle Beach
- Bird Island





