
Holiday 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.

5BR*Dbl. Master*1 Block to Beach* GAMEROOM* Yaupon
3-4 min. walk to the beach! 2 night min stay June 2024. 4 night min stay July-August 2024. Stay at our spacious "American Dreaming" cottage on Yaupon Beach/Oak Island and check off all of your vacation boxes! Sit by the firepit and listen to the sounds of the crashing waves, which are only 1 block away. Head down to the beach during the day and then cool off in our private stock tank pool while your kids play ping pong in the game room. Enjoy a short 10 minute drive down to historic Southport!

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 Condo With Balcony and Pool
Welcome to our beachfront 1 bedroom condo at "The Riggings"! Enjoy the stunning ocean views from the comfort of your own private balcony. Inside, you'll find a cozy queen size bed, perfect for a romantic getaway or a solo retreat. We also have a twin size bunk bed and a pull out couch, making it perfect for families or groups of friends. Whether you're looking for a romantic escape, a family vacation, or a relaxing solo trip, our beachfront condo has everything you need for a perfect stay.

SeaScape-Top Floor Ocean Views & Dips in the Pool!
You'll love sipping coffee and watching the sunset from the front deck of this beautiful and much sought after 3rd floor ocean view condo with private pool and a beach access is just a short walk away. This NON-SMOKING condo includes, 2 flat screen SmartTVs, cable, & private WiFi. The kitchen contains all essential tool, a limited amount of spices/staples. There's also a Keurig with a variety of coffee pods for your enjoyment. The queen sofa bed sleeps 2 comfortably. No pets are allowed.

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.

Maggie’s Oasis
Welcome to Maggie's Oasis! With a lush landscape, sparkling pool/spa, and ample entertainment space, this private retreat is perfect for relaxation and gatherings. Fully fenced-in for safety, it's a haven for both humans and pets. Enjoy the tranquil outdoor ambiance, stunning interior, and well appointed rooms and kitchen. Walking distance to grocery stores, shopping and restaurants or just a short 10-15 minute drive to historic downtown Wilmington or beautiful Wrightsville beach.

Private Heated Pool, Steps to Beach, Pets OK
Happy Hour at OKI by Hearth and Horizon Family Getaways – Just a 4-min verified walk to the beach! 1. Enjoy a private pool with fountains, 2. outdoor dining under a pergola, and a fire pit (wood provided). 3. Game room features air hockey, arcade (Mortal Kombat), kids’ books & toys. 4. Relax in 2 king bedrooms, including a spa-style primary bath with rain shower. Perfect for families looking for beach fun and cozy comfort! 5. Fenced backyard for your fur baby to run around!

The Coastal Coconut: Beautiful Ocean View Condo
This spectacular ocean view condo with top notch 2022 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.

Making Waves 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.

Beachfront condo w/pool and great views
Kick back and relax in this calm, stylish space that is oceanfront. Enjoy coffee or cocktails in the deck while watching the waves. Just steps from the beach with a garage to store all your beach and ocean toys. Everything you need is provided for your stay. Enjoy the pool and grilling area in the complex. Free parking on site. The boardwalk is 1.5 miles away with plenty of things to do and places to eat but far enough away that you have peace and quiet.

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

Oceanfront Retreat w/ Pool - Dog Friendly

Hang Zen! This house has it all!

8-bedroom, 8-bathroom with Elevator & Heated Pool

Shake it Off

Luxe Oceanfront Escape | 4BR w/ Pool & Views!

Mermaid Retreat* Private Pool* Pet Friendly

Beautiful home with pool & marsh view ‘Breakaway’

5 o’clock Always
Condo rentals with a pool

BEACHFRONT w/ pool, near boardwalk, amazing views!

☀️Oceanfront with Beach Access "Carla's Cabana"☀️

Beach vacation condo at Ft Fisher! Riggings

OCEANFRONT & ON the BOARDWALK! Unbelievable VIEWS

Coastal Escapes Luxury 3 bdrm Oceanfront Condo

*Renovated* Top Floor Oceanfront Condo w/ Pool

The Great Wave

Oceanfront Condo, Spacious Private Deck & Pool!
Other holiday rentals with a pool

Family Tides, Beautiful views, Pool, Hot tub!

Private Heated Pool, Tiki Hut- 10min walk to beach

The Oak Tree Bungalow. Relaxed Island Living

New, Oceanfront, 50 Steps to the Sand, Pool, Views

Oceanview Condo, Pool, 2 min walk to the sand

Oceanfront End Unit Condo Sunrise and Sunset Views

Kid Friendly Luxe: Kayak Our Dock + 2 Carts, Clubs

3 Putt Paradise
When is the best time to visit Oak Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 AUD | $234 AUD | $285 AUD | $336 AUD | $407 AUD | $470 AUD | $452 AUD | $434 AUD | $366 AUD | $264 AUD | $268 AUD | $240 AUD |
| 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 holiday rentals with a pool in Oak Island

Total holiday rentals
Explore 600 holiday rentals in Oak Island

Nightly prices starting at
Oak Island holiday rentals start at $75 AUD per night before taxes and fees

Verified guest reviews
Over 6,590 verified reviews to help you choose

Family-friendly holiday rentals
530 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 180 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
600 of Oak Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oak Island rentals

4.6 Average rating
Oak Island stays receive an average rating of 4.6 out of 5 from guests
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- Myrtle Beach Boardwalk
- Wrightsville Beach, NC
- Barefoot Resort & Golf
- South Beach
- Cherry Grove Point
- Family Kingdom Amusement Park
- Dunes Golf and Beach Club
- Futch Beach
- Myrtle Beach SkyWheel
- Wrightsville Beach
- North Carolina Aquarium at Fort Fisher
- Surf City Pier
- Ripley's Aquarium of Myrtle Beach
- Cherry Grove Fishing Pier
- Seahorse Public Beach Access
- Arrowhead Country Club
- Jungle Rapids Family Fun Park
- Myrtle Waves Water Park
- Salt Marsh Public Beach Access
- Myrtle Beach State Park
- Carolina Beach Lake Park
- Tidewater Golf Club
- Airlie Gardens
- The Pavilion Park




