
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.

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!

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.

Oceanfront | Breathtaking Sunrise l Pool
Peach on the Beach is a modern & newly renovated one bedroom condo, with a spacious open living room/kitchen area. This is a corner unit, which provides breathtaking views with access to a large covered oceanfront deck. Just a 2 minute walk to the beach. Perfect location for the sunrise and sunset lovers! Enjoy the ocean sunrise from the deck or beach & directly accross the street at the Fort Fisher Air Force Recreational Center are the best sunsets on the river.

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.

2Br, Beach Access-Indoor Heated Pool!
Welcome to Surfrider! 2bd and 2 bath, 2nd floor condo, with elevator access. Property is across the street to your private beach access. Enjoy an indoor heated pool - open year round( maintenance on Mar 23th-27th and Apr 14th-24th pool closed), sauna, outdoor pool (seasonal), fitness center, basketball court, shuffleboard, and playground. Internet, cable, and Roku. Short walk across the street to your private beach access. Quiet and family friendly.

Oceanfront Third Floor Condo w/pool (Riggings E-3)
Beautifully furnished top floor, end unit overlooking the ocean and pool. Watch the dolphins swim by from your private balcony. Just steps away from the beach. There is also an oceanfront pool where you can spend the day soaking in the suns rays. Surf fishing is superb directly in front of the condo due to a large rock formation next to Fort Fisher. ** Maximum of THREE (3) adults**

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

Oceanfront End-Unit 1stFLR/pool Shamrock Sands M1

2 Min Walk to Beach | Heated Pool | Golf Cart

Beach Bum Rest & Relax (With Salt Pool)

Steps to the Beach | Carolina & Kure - Sleeps 10!

Ocean Front Condo at Kure Beach The Pink Ruby

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

Captain’s Watch Home

1 Perfect Alignment Oceanfront - Elevator - Perfec
Apartment rentals with a pool

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

Beach vacation condo at Ft Fisher! Riggings L1

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

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

Newly Renovated Panoramic OCEANFRONT Views

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

A Wave From It All - Carolina Beach Condo

Cozy Oceanfront Surf Condo w/ Pool & Beach Access
Other holiday rentals with a pool

The Waterway Treehouse @ Wrightsville Beach

Gorgeous 4 BR with Ocean Views & Pool

Luxury Oceanfront Penthouse Condo with Pool

Oceanfront balcony views | pool & beach access

Oceanfront 3BR | Massive Private Deck | Sleeps 10

Oceanfront 2BR Designer | Pool | Lift | EV

The Blue Pearl

The Hamlet House-pool/fenced yard/pet friendly.
Destinations to explore
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- 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
- Cherry Grove Fishing Pier
- North Carolina Aquarium at Fort Fisher
- 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
- Fort Fisher State Historic Site
- Soundside Park
- Freeman Park
- Fort Fisher State Recreation Area
- Greenfield Park
- Oak Island Lighthouse
- Johnnie Mercer's Fishing Pier
- Long Leaf Park





