
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.

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.

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.

Cozy Oceanfront Surf Condo w/ Pool & Beach Access
Just RENOVATED! Conveniently located directly in front of its own private beach access, this simply elegant condo is just minutes from everything Carolina Beach has to offer. Enjoy the boardwalk, local restaurants, and the beach right outside your door. Captain’s Corner provides a place where you can relax and make lasting memories at Carolina Beach. There is a private beach access, private pool, and private outdoor shower located at the condo complex (Summer Season) along with free parking.

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!

Finns Up- Dog Beach. Ocean Views. Clean & Comfy!
Wake up to sweeping ocean views at Finn’s Up, your perfect Pet-Friendly, Carolina Beach escape. Ideally located beside the North End Pier, this bright, beautifully designed two-bedroom condo invites you to start your day with coffee on the porch daybed, then step straight into sun-filled beach days and relaxing coastal evenings. Just steps from the island’s only year-round dog-friendly beach makes this a perfect getaway destination for the entire family. A Salt And Linen Stays property.

Best Location! Beachfront-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.

Shorething- Oceanfront-Poolview-3rd floor-Sleeps 6
Amazing views! Your 3rd-floor private patio overlooks the pool and offers beautiful views of the ocean. Sip coffee and watch the sunrise. You can hear the tranquil sound of waves on the beach only steps away. A great 3rd-floor end unit condo with 1 bedroom and a bunkbed alcove (sleeps 4). Less than a mile from the Historic Fort Fisher and the North Carolina Aquarium or the Ferry to Southport and Baldhead island. Minutes away from everything pleasure island has to offer.

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.

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.

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!

Dual master, end unit condo with amazing views
Sit back and relax at our spacious 2 bedroom, 2.5 bath OCEAN front condo! Recently renovated and new stainless steel appliances for your perfect vacation getaway. This condo provides an incredible ocean view, comfortable living, and covered parking. Only a few minutes away from shopping, parks, and restaurants, there is plenty to see and explore.
Popular amenities for Pleasure Island rentals with a pool
House rentals with a pool

After Dune Delight

Pool | Pet friendly | 10 mins to Beach

Luxury Oasis - Pool, Jacuzzi, Golf Cart!

Mermaid Retreat* Private Pool* Pet Friendly

Beach Bum Rest & Relax (With Salt Pool)

Ocean Front Condo at Kure Beach The Pink Ruby

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

Captain’s Watch Home
Condo rentals with a pool

Ocean View! No Pet Fee! Come Relax @ The Escape CB

Carla's Cabana ~ Oceanfront, Balcony w/view & Pool

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

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

Ocean front, 1 bedroom condo w/ pool, Reef Relief

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

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

Spectacular Views! - ON The Beach w/Access
Other holiday rentals with a pool

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1

High Tide Hideaway

Luxury Oceanfront Penthouse Condo with Pool

Oceanfront 3BR at Salt & Light

2 Min Walk to Beach | Heated Pool | Golf Cart

Oceanfront 3BR | Massive Private Deck | Sleeps 10

The Blue Pearl

Heated Pool, Bowling, Pool Table, 2 Min to Sand
Destinations to explore
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Savannah Holiday rentals
- Charleston Holiday rentals
- Hilton Head Island Holiday rentals
- Virginia Beach Holiday rentals
- North Myrtle Beach Holiday rentals
- Asheville Holiday rentals
- Raleigh Holiday rentals
- Wilmington Holiday rentals
- Richmond Holiday rentals
- Outer Banks Holiday rentals
- Rentals with a sauna Pleasure Island
- Beachfront rentals Pleasure Island
- Waterfront rentals Pleasure Island
- Condo rentals Pleasure Island
- House rentals Pleasure Island
- Pet-friendly rentals Pleasure Island
- Cottage rentals Pleasure Island
- Hotel rooms Pleasure Island
- Rentals with beach access Pleasure Island
- Rentals with a hot tub Pleasure Island
- Rentals with lake access Pleasure Island
- Private suite rentals Pleasure Island
- Serviced apartment rentals Pleasure Island
- Apartment rentals Pleasure Island
- Aparthotel rentals Pleasure Island
- Family-friendly rentals Pleasure Island
- Rentals with a kayak Pleasure Island
- Townhouse rentals Pleasure Island
- Rentals with pools New Hanover County
- Rentals with pools North Carolina
- 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
- St James Properties
- Fort Fisher State Historic Site
- Jungle Rapids Family Fun Park
- Airlie Gardens
- Freeman Park
- Soundside Park
- Fort Fisher State Recreation Area
- Greenfield Park
- Oak Island Lighthouse
- Johnnie Mercer's Fishing Pier
- Long Leaf Park





