
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.

The Tropical Palm-Ocean View, Pool, Heart of CB
Ocean-view condo just a short walk from the beach and downtown Carolina Beach! This entire 1-bedroom, 1.5-bath condo features a private balcony with ocean and fireworks views, a full kitchen, and comfortable living space. Sleeps 4 with a queen bed and queen pull-out sofa. Perfect for couples, small families, or a girls getaway. Walk to the beach, restaurants, and shops for an easy, relaxing stay. Pool opens Memorial Day Weekend Please no golf carts on the property, as they will be towed.

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

Private Pool House with Hot Tub!
Luxury experience in a beautiful setting. Tucked behind the main house, this private guest cottage is located in the heart of Carolina Beach, within walking/biking of the beach and boardwalk. 5 blocks from the ocean/public beach access. Short walk or bike to state park, tennis courts, greenway, shops and restaurants. The home features a beautifully landscaped private outdoor covered lounging and dining area with fans, fire pit and Smart TV. Newly added private hot tub and expanded grill area.

Kure Cabana*Cottages@Kure*Ocean View*Pool*Historic
Charming Renovated Cottage w/ Community Pool ● Pack lightly for this quaint newly renovated 3-bedroom cottage with Front Porch ● Free Parking ●Outdoor pool for guests ● All the comforts of home; just perfect for a beach getaway for 4 ● 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!

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 ✨

Light-filled/Beach-Ocean views/Top floor condo
Top Floor Bright Airy condo. No carpet. Perched ocean, beach/park views front patio, marsh back balcony, surfer’s paradise, wave sounds, cotton bed linens, bath towels. Beach chairs. Stocked kitchen. Self check-in. North island privacy by entrance to Freeman Park/across Carolina Beach Pier&Tiki/1.5 mi bike/drive/walk to center of town. Steps to ocean, pool set in marsh, grilling stations/picnic tables. Washer/dryer. King bed+sofa bed. Peace. 4 guests max. No smoking. No pets. Come relax!

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.

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.

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.

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.

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

The Oasis - Heated POOL - Tiki Bar - Beach Life!

Mermaid Retreat* Private Pool* Pet Friendly

The Seascape - Pool & 10 mins from Beach/Downtown

Dog-friendly Home w Pool - 2 min walk to Beach!

Home with Salt water pool and bamboo garden view

Pool | Pet friendly | 10 mins to Beach

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1

Kid-Friendly Luxe, Kayak Our Dock, 2 Carts + Clubs
Condo rentals with a pool

Rise and Shine! Beach, pool, & amazing views!

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

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

Spectacular Views! - ON The Beach w/Access

Oceanfront Condo, Spacious Private Deck & Pool!

OCEANFRONT PARADISE WITH SPECTACULAR OCEAN VIEWS

Ocean Front, Top Floor Unit- Carolina Beach

The Coastal Coconut: Beautiful Ocean View Condo
Other holiday rentals with a pool

Kure Me Away, Rec center, In/Outdoor pools&hot tub

Dolphins Delight Oceanfront Condo

Updated beachfront condo with stunning views!

The Serene at Carolina Beach

5 blocks to Beach | Pickleball | Pets | Firepit

The Blue Pearl

The Waterway Treehouse @ Wrightsville Beach

Ocean Breeze Oasis ~ Elevator ~ Pool ~ Hot Tub
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- 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





