
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.

Take a Break at Shore Break!
First floor, beautiful one bedroom oceanfront condo with all the amenities you need for a relaxing vacation by the sea. Fully stocked kitchen with granite countertops and new furnishings to ensure a comfortable and stylish stay. The large deck is perfect for outdoor dining or relaxing while taking in the ocean views. Wake up in the King size bed to the sound of the waves! Enjoy the resort style pool and picnic area. WIFI, coffee, beach chairs and linens included. Free Parking. Laundry on-site

OCEANFRONT PARADISE WITH SPECTACULAR OCEAN VIEWS
This 3rd floor Unit with spectacular views of the Ocean. Newly renovated Kitchen w/ granite countertop, Fully equipped Kitchen with New appliances, utensils, Keurig coffee maker & spice rack! New platform bed, NEW Serta memory foam mattress, bedding, linens (including beach towels/ sheets), New Patio floor, New furniture, sofas, decor, dimmable floor lamps. 2 New Samsung Smart TV’s wall mounted. New Ceiling Fans, New Flooring, & Paint throughout. LED Patio lights for patio dining. Washer dryer

Surfrider Siesta -Indoor Pool -Hot Tub - Elevator
Relax with the family at this peaceful retreat. Surfrider Siesta is a very comfortable, family friendly place to stay. Fully equipped with all the cooking essentials, washer & dryer unit within condo, WiFi and cable. Private beach access is 100 steps from the front door. The complex has three outdoor pools which are seasonal and a recreational building with a heated indoor pool open all year round. It also has sauna, hot tub, gym and changing rooms. Sorry no pets allowed in rentals as per HOA.

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.

Vista North (OCEAN+MARSH+POOL+Parking)
This is the perfect escape for those looking for waterfront cozy chic luxury. Just steps away from a pristine oceanfront preserve and biking distance to the boardwalk, restaurants and nightlife. Our recently updated stylish condo will give you an emersion of coastal beauty and an array of local attractions along with access to marsh side pool, bikes and grills. Start your day with a cup of coffee and an ocean sunrise and unwind with a glass of wine for an unmatched marsh view sunset.

Cowabungalow - Luxury Condo
This custom LUXURIOUS 1-bedroom oceanfront sleeps 4 w/pull-out couch and is completely NEW inside. This unit is oceanfront, 2nd story w/elevator, covered parking in a gated parking lot, and a fully stocked kitchen, park the car & never have to drive during your stay! Right on the CB boardwalk w/ many choices for ocean view restaurants, etc. Pet friendly with an additional $60 cleaning fee per pet and early check-in and late check-out fee $150 for each request w/ 2-day notice.

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.

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

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

Shake it Off

Family Beach Escape 2nd Row Pool Elevator & Views

Brand New w/ Pickleball Court & Heated Pool

Mermaid Retreat* Private Pool* Pet Friendly

5 o’clock Always

Pool | Views | Sleeps 8 | Linens | Yacht Drive

Brezza Fresca w/ a private pool In Carolina Beach
Condo rentals with a pool

Beachfront Condo, Steps to the Beach

Beach Sol Oceanfront w/pool & private beach access

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

Best Location! Beachfront-Boardwalk-Pool-Balcony

The Great Wave

Beach, Pools, Gym & Hot Tubs | Fun & Sun Villa

Surf Shack! Carolina Beach Amazing Location!

Love SPT Year Round? Winter Seasonal Rates!
Other vacation rentals with a pool

Oceanfront Condo | Beach + Lake Views, Sleeps 5!

St James - King Bed & Porch (No Cleaning Fee)

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

Living the Coastal Dream in Southport

Oceanfront • Steps to Sand • Sleeps 8 • 1st Floor

Southport Serenity
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$34,298 GYD | G$32,416 GYD | G$39,526 GYD | G$46,637 GYD | G$56,466 GYD | G$65,249 GYD | G$62,740 GYD | G$60,230 GYD | G$50,819 GYD | G$36,598 GYD | G$37,226 GYD | G$33,252 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$10,457 GYD per night before taxes and fees

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

Family-friendly vacation rentals
530 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

4.6 Average rating
Oak Island stays receive an average rating of 4.6 out of 5 from guests
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- Myrtle Beach Boardwalk
- 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
- Arrowhead Country Club
- Seahorse Public Beach Access
- Jungle Rapids Family Fun Park
- Myrtle Beach State Park
- Myrtle Waves Water Park
- Airlie Gardens
- Salt Marsh Public Beach Access
- Carolina Beach Lake Park
- Tidewater Golf Club
- The Pavilion Park
- Long Beach




