
Holiday rentals with a pool in Pleasure Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pleasure Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Coral Surf C-1 2BR/2BTH, 240v ev & 110v outlet
This is a first level, true oceanfront, two bedroom unit, with two full private baths. Each bedroom has a queen size bed, and there is a queen sleeper sofa in the living room. This condo can accommodate six people. We are located south of the town with just a ten minute walk to the boardwalk. I provide all bed linens, bath towels and paper products. This unit has three smart televisions. We have a small pool and our own private walkway to the beach with showers. EV charger in parking space.

River Road Retreat - Heated Private Pool, Pond, Fi
Private pool, pond views, gardens, and a 10 minute drive to the beach! This home backs up to a nature preserve. Relax by the pool and tiki bar area watching TV or enjoying music. Pool Heater: Our pool is open and maintained year round. The pool heater can reliably generate heat as long as the outside temperatures are above 50 degrees which will generally be from March to November, however in our area it is not unusual for us to have warm days at any time of year. Many vacation rental propert

Oceanfront • Hot tub • Indoor Pool • Gym
👋🏼 Hi there! This has been my family’s happy place for years … where grandkids hunted seashells, mornings started with coffee and sunrise, and life just slowed down. We’re sharing it so your family can make those same memories, with all the little touches that make coastal trips easy & fun Your stay comes with a personal concierge- offering optional add-ons (beach setups, stocked fridges, and curated local experiences). ✨ We offer the most amenities in the area for an elevated experience ✨

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.

Poolside retreat close to Beaches/Dtwn/UNCW
NEWLY RENOVATED fully private studio overlooking the saltwater pool. Cozy bedroom space with queen bed, two relaxing chairs, Chic & modern kitchenette, compact bath with walk-in shower & more! The guesthouse is conveniently located: Historic Downtown with a Riverwalk, dining, entertainment and its rich culture is minutes away. 13 minutes to Wrightsville Beach; 20 minutes to Carolina Beach No shortage of restaurants, live music, parks, Brewery's, shopping, outdoor activities and much more.

Hanby Hideaway*Cottages@Kure*Pool*Beach*Historic
Charming Renovated Cottage ● Pack lightly for this quaint (small) Studio upstairs tiny cottage with Front Deck ● Free Parking ●Outdoor pool for guests (Seasonal) ● All the comforts of home; just perfect for a beach getaway for 2 ● One short block to the beach, Kure Beach Pier, restaurants and arcade are a quick stroll away ● Drive to Carolina Beach Boardwalk for famous Britt's doughnuts, Fort Fisher Museum, Aquarium and the Ferry that goes to Southport for an adventure you're sure to enjoy!

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.

Perfect Beachfront Location-Boardwalk-Pool-Balcony
Unbeatable location directly on the famous Carolina Beach Boardwalk! Step outside the door and you’re just seconds away from the beach and ocean, where you can enjoy swimming, sunbathing, and even spotting dolphins from the shoreline. The boardwalk itself is a hub of activity, with bars, restaurants, shops, and live music just steps away. Whether you’re in the mood for a casual meal, a fun night out, or exploring the local boutiques, you’ll find it all within walking distance.

Fully Renovated Beautiful Oceanfront 2 BR Condo
Come feel at home in our newly renovated and newly furnished oceanfront condo with beautiful 2nd floor views of the ocean from the master bedroom, living room, and deck. Extra detail was given to this unit so it would feel like home for families or couples. Only a relaxing 15 minute walk to the one of the highest rated boardwalks on the east cost! Includes access to the pool and two guest parking spaces. Beach access is just steps away. You'll love this place!

The Oasis - Heated POOL - Tiki Bar - Beach Life!
WELCOME to THE OASIS Beach House! Ready for the ULTIMATE Vacation!? The Oasis features a full-size saltwater pool, fire pit, tiki bar, grill, and an outdoor TV. This backyard beauty has everything you could want! Located just 7 blocks to the ocean in Carolina Beach, spend days on the sand and evenings under the string lights around the pool, bar, or fire pit. Brand new listing with beautiful furnishings. Pool heated during shoulder season on request with fee.

Oceanfront Condo, Spacious Private Deck & Pool!
Welcome to The Endless Summer CB Condo! Whether you're visiting Carolina Beach as a couple, with family, or a group of friends, The Endless Summer CB is your perfect oceanfront paradise! The home has been designed with all of our guests' comfort in mind. Enjoy breathtaking views from your spacious patio or the miles of pristine coastline just steps away with a private beach access. Minutes to downtown CB, the Boardwalk, restaurants, and more!

No Cleaning Fee! New Condo w/ Waterfront Pool
Visit the most adorable seaside village! Southport, with it's picturesque waterfront, fantastic restaurants, and adorable shops, has something for everyone. When you feel like staying closer to home, the pool will be calling your name for soaking in the sun while watching the ships sail by, and your private balcony is the perfect spot to sip a cup of coffee while watching the sunrise over the water.
Popular amenities for Pleasure Island rentals with a pool
House rentals with a pool

After Dune Delight

Pool | Pet friendly | 10 mins to Beach

2 Min Walk to Beach | Heated Pool | Golf Cart

Mermaid Retreat* Private Pool* Pet Friendly

Beach Bum Rest & Relax (With Salt Pool)

Ocean Front Condo at Kure Beach The Pink Ruby

Heated Pool, Bowling, Pool Table, 2 Min to Sand

Captain’s Watch Home
Condo rentals with a pool

SeaScape-Top Floor Ocean Views & Dips in the Pool!

*Renovated* Top Floor Oceanfront Condo w/ Pool

A Wave From It All - Carolina Beach Condo

Cozy Oceanfront Surf Condo w/ Pool & Beach Access

Dune Our Thing! With an amazing view!

Light-filled/Beach-Ocean views/Top floor condo

Spectacular Views! - ON The Beach w/Access

Shorething- Oceanfront-Poolview-3rd floor-Sleeps 6
Other holiday rentals with a pool

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1

Luxury Oasis - Pool, Jacuzzi, Golf Cart!

Oceanfront 3BR | Massive Private Deck | Sleeps 10

Oceanfront 2BR Designer | Pool | Elevator | EV

Seas the Day | 2BR Oceanfront Condo

The Blue Pearl

Vacation Condo in Kure Beach! The Riggings I1

Kid-Friendly Luxe, Kayak Our Dock, 2 Carts + Clubs
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- Rentals with pools New Hanover County
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- Rentals with pools United States
- Wrightsville Beach, NC
- Carolina Beach Boardwalk
- Cherry Grove Point
- Kure Beach Pier
- Wrightsville Beach
- North Carolina Aquarium at Fort Fisher
- Cherry Grove Fishing Pier
- University of North Carolina Wilmington
- Wilmington Riverwalk
- Surf City Pier
- Carolina Beach Lake Park
- Carolina Beach State Park
- Bird Island
- Fort Fisher State Historic Site
- St James Properties
- Jungle Rapids Family Fun Park
- Airlie Gardens
- Freeman Park
- Soundside Park
- Fort Fisher State Recreation Area
- Johnnie Mercer's Fishing Pier
- Greenfield Park
- Long Leaf Park
- Oak Island Lighthouse





