
Holiday rentals with a pool in Pleasure Island
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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

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.

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!

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.

Kure Me Away, Rec center, In/Outdoor pools&hot tub
Forget your worries in this spacious and serene space. Newly renovated - Beautifully decorated and appointed. Well stocked gourmet kitchen with high quality appliances. Upper and lower balconies with plenty of seating. Private master bedroom balcony for awesome sunrises. Located at the quiet end of the island with much less crowded beaches, but still with easy access to dining and entertainment. Linens and towels (beds made) included. **Pase note**The fireplace is nonworking.

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.

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.

Dolphins Delight Oceanfront Condo
Escape to this stunning oceanfront one-bedroom condo designed for a relaxing coastal retreat. Wake up to breathtaking ocean views from the living room and bedroom, or step onto your private deck overlooking the sea. Enjoy the soothing sound of waves with morning coffee or evening relaxation. Dolphins are often seen gliding by at sunrise. Guests also enjoy a resort-style pool, picnic area, Wi-Fi, linens, two beach chairs, and convenient parking. 🐬🌊☕
Popular amenities for Pleasure Island rentals with a pool
House rentals with a pool

After Dune Delight

Mermaid Retreat* Private Pool* Pet Friendly

The Seascape - Pool & 10 mins from Beach/Downtown

Pool | Pet friendly | 10 mins to Beach

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

Home with Salt water pool and bamboo garden view

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1

Captain’s Watch Home
Condo rentals with a pool

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

The Coastal Coconut: Beautiful Ocean View Condo

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

Spectacular Views! - ON The Beach w/Access

Oceanfront • Hot tub • Indoor Pool • Gym

Blue Latitude

Dune Our Thing! With an amazing view!

SeaScape-Top Floor Ocean Views & Dips in the Pool!
Other holiday rentals with a pool

5 blocks to Beach | Pickleball | Pets | Firepit

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The Blue Pearl

The Waterway Treehouse @ Wrightsville Beach

Oceanfront 3BR | Massive Private Deck | Sleeps 10

Luxury Oceanfront Penthouse Condo with Pool

Ocean Breeze Oasis ~ Elevator ~ Pool ~ Hot Tub

Sunrise Tides on Kure Beach
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- Wrightsville Beach, NC
- Carolina Beach Boardwalk
- Cherry Grove Point
- Wrightsville Beach
- Kure Beach Pier
- 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
- Jungle Rapids Family Fun Park
- St James Properties
- Fort Fisher State Historic Site
- Airlie Gardens
- Freeman Park
- Soundside Park
- Fort Fisher State Recreation Area
- Johnnie Mercer's Fishing Pier
- Greenfield Park
- Oak Island Lighthouse
- Long Leaf Park





