
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.

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

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.

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!

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.

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.

Amazing Ocean Views!
First Floor beach retreat with fantastic ocean views. Enjoy your morning coffee or afternoon cocktail from one of the two balconies. Catch the sunrise from your bed or get up and take a stroll along the beach. Condo has been recently updated with modern appliances, including stainless steel refrigerator, stove/oven, microwave and gorgeous as spa like bathrooms. Beach chairs all supplied. Guests who brings pets will be charged $25 per pet and this is non-refundable.

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.

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.

After Dune Delight
Welcome to the After Dune Delight Condo where you can relax and unwind with amazing Beachfront views! A modern first level unit, with all the comforts of home and conveniently located close to shopping, dining, and nightlife in Carolina Beach. Includes private beach access, 2 covered parking spaces, pool, barbecue areas, and much more!
Popular amenities for Pleasure Island rentals with a pool
House rentals with a pool

Oceanfront End-Unit 1st FLR w/pool Shamrock Sands

Luxury Oasis - Pool, Jacuzzi, Golf Cart!

Mermaid Retreat* Private Pool* Pet Friendly

Home with Salt water pool and bamboo garden view

Spacious Coastal Stay | Games, Beach, King Suite

Captain’s Watch Home

BIG DECK! Tiki Bar! Oceanfront Pool! Elevator!

All I want is….this Christmas house~
Apartment rentals with a pool

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

Oceanfront End Unit Condo with Pool (Riggings D-2)

Oceanfront • Hot tub • Indoor Pool • Aquarium

Newly Renovated Panoramic OCEANFRONT Views

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

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

A Wave From It All - Carolina Beach Condo

Spectacular * Oceanfront Condo - Once Upon A Tide
Other holiday rentals with a pool

The Waterway Treehouse @ Wrightsville Beach

Take a Break at Shore Break!

Oceanfront balcony views | pool & beach access

Sea View Villa~Ocean Front~Newly Renovated~Pool

Oceanfront 2BR Designer | Pool | Lift | EV

Seas the Day | 2BR Oceanfront Condo

The Blue Pearl

Bears Beachfront- Oceanfront. Luxury. Dog Friendly
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- 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
- Surf City Pier
- University of North Carolina Wilmington
- Carolina Beach Lake Park
- Wilmington Riverwalk
- Carolina Beach State Park
- Jungle Rapids Family Fun Park
- Bird Island
- Fort Fisher State Historic Site
- Airlie Gardens
- St James Properties
- Soundside Park
- Fort Fisher State Recreation Area
- Freeman Park
- Oak Island Lighthouse
- Greenfield Park
- Johnnie Mercer's Fishing Pier
- Long Leaf Park





