
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.

Oceanfront 2 BR/2.5 BA Condo
Come enjoy our townhome in the Oak Island Beach Villas #206 located on Caswell Beach! Lounge on the oceanside deck incorporated into the living room, or enjoy a private balcony off the main bedroom upstairs overlooking the Atlantic Ocean! Make the most amazing memories watching the dolphins, observing the sea turtles lay their eggs, and watching the most amazing sunsets/sunrises you'll ever see. This condo is right across from the golf course. This is by far the most beautiful beach ever!

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.

Luxury Oceanview Home - Steps to Beach
Indulge in the luxury of beachside living at Casa Allora, a stunning Oak Island Beach House. This exquisite newly built 5-bedroom, 3.5-bathroom retreat comfortably accommodates 10 guests. Revel in modern comforts with amenities like a private pool, patio, BBQ grill, 3 king bedrooms, and 2 oversized front decks. Whether you love a cup of coffee while watching the sunrise over the ocean or enjoying a glass of wine at sunset with the breeze in your hair, Casa Allora has it all!

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.

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 #8, Pool and 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.

Gather at the Beach! | Ocean Views | Elevator
FANTASTIC BEACH ACCESS & Heated Pool Perfect for Extended Families: -Sleeps 18 People -6 Bedrooms & 5 Bathrooms -Dine Together Indoors & Out -Fantastic Kitchen: 2 Fridges & 2 Dishwashers -Additional Kitchenette -Private Heated* Saltwater Pool -Elevator -Pool Toys, Towels, Chairs Provided -Linens Provided -Free Beach Parking for 8 Cars -EV Charger -Gas Grill -4 Balconies -Amazing Ocean Views! *Sorry, we can't heat the pool November-February.

Beach Cottage Getaway with a private pool!
Relax with the whole family at our beach cottage - enjoy a short 1/2 mile walk to the beach or the intercoastal or enjoy the private new inground pool with loads of decking, seating for the whole family and a screened in porch! Lots of room to spread out and great outdoor entertainment area with a fire pit. Large living room, dining room and kitchen and a workspace as well. Perfect spot to enjoy all that Oak Island has to offer!
Popular amenities for Oak Island rentals with a pool
House rentals with a pool

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

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

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

Family Tides, Beautiful views, Pool, Hot tub!

Ocean Front Paradise

Fox On The Beach - across from beach, heated pool

Beautiful home with pool & marsh view ‘Breakaway’

Oak Island 2nd Row 5 BDR Beach Home w/Private Pool
Condo rentals with a pool

Coastal Escapes Luxury 3 bdrm Oceanfront Condo

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

Oceanfront • Hot tub • Indoor Pool • Aquarium

Newly Renovated Panoramic OCEANFRONT Views

Sand Surf & Sunset Ocean View Condo - 2 Bed 2 Bath

Sea-clusion: A ground floor beach front condo

Dual master, end unit condo with amazing views

Stones Throw to downtown Southport
Other vacation rentals with a pool

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

4bed- Family Fun: Game Room + Pool + BBQ + Hot Tub

Harbor Lights Resort | Waterfront, Pool & Dock!

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

Sea View Villa~Ocean Front~Newly Renovated~Pool

Walkin' on Sunshine by Out of Bounds Retreats

The Oak Tree Bungalow. Relaxed Island Living

Oceanfront 2BR Designer | Pool | Elevator | EV
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 CAD | $278 CAD | $380 CAD | $311 CAD | $377 CAD | $435 CAD | $419 CAD | $402 CAD | $339 CAD | $271 CAD | $264 CAD | $311 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 $84 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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