
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.

Masonboro Manor*Cottages@Kure*Pool*Beach*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 7 ● 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!
ValueFamilyWalkability

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
LocationValueComfort

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.
FamilyValueDecor

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 ✨
LocationFamilyHospitality

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.
FamilyValueCheck-in

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.
LocationFamilyQuiet

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.
LocationValueView

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.
LocationFamilyGetting around

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!
FamilyLocationAccuracy

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.
LocationValueCleanliness

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.
ValueFamilySleep quality

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.
ValueLocationAccuracy
Popular amenities for Pleasure Island rentals with a pool
House rentals with a pool

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1
LocationFamilyParks

After Dune Delight
LocationValueHospitality

Pool | Pet friendly | 10 mins to Beach
ValueLocationKitchen

Luxury Oasis - Pool, Jacuzzi, Golf Cart!
LocationFamilyKitchen

Mermaid Retreat* Private Pool* Pet Friendly
LocationValueAir conditioning

Ocean Front Condo at Kure Beach The Pink Ruby
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Kid-Friendly Luxe, Kayak Our Dock, 2 Carts + Clubs
LocationFamilyCheck-in

Game Room + Backyard Retreat
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Condo rentals with a pool

Carla's Cabana ~ Oceanfront, Balcony w/view & Pool
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SeaScape-Top Floor Ocean Views & Dips in the Pool!
FamilyLocationCheckout

Oceanfront Third Floor Condo w/pool (Riggings E-3)
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Ocean front, 1 bedroom condo w/ pool, Reef Relief
LocationValueParking

Newly Renovated Panoramic OCEANFRONT Views
ValueFamilyComfort

Carolina Beach Condo w/ Pool, Parking & Sleeps 6
LocationValueView

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

A Wave From It All - Carolina Beach Condo
FamilyValueIndoor spaces
Other holiday rentals with a pool

The Waterway Treehouse @ Wrightsville Beach
LocationNearbyAmenities

Gorgeous 4 BR with Ocean Views & Pool
FamilyLocationComfort

Luxury Oceanfront Penthouse Condo with Pool
LocationFamilyDecor

2 Min Walk to Beach | Heated Pool | Golf Cart
FamilyLocationAccess

Oceanfront 3BR | Massive Private Deck | Sleeps 10
FamilyLocationAccess

The Blue Pearl
FamilyLocationCondition

Seas the Day | 2BR Oceanfront Condo
LocationFamilyAccess

Carolina's Perfection: Heated Pool w/ Rooftop Spa
FamilyLocationNearby
Destinations to explore
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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
- Surf City Pier
- Carolina Beach Lake Park
- Wilmington Riverwalk
- Carolina Beach State Park
- Bird Island
- Jungle Rapids Family Fun Park
- St James Properties
- Airlie Gardens
- Freeman Park
- Soundside Park
- Fort Fisher State Recreation Area
- Greenfield Park
- Oak Island Lighthouse
- Johnnie Mercer's Fishing Pier
- Long Leaf Park
- Oak Island Pier





