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Holiday rentals with a pool in Kailua

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kailua

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A spacious bedroom features a king bed draped with sheer white fabric, creating an airy ambiance. Two stylish chairs are positioned beside large windows that overlook lush greenery. A natural fiber rug covers the hardwood floor, complemented by a simple wooden bench at the foot of the bed.
Apartment in Kahuku
4.93 out of 5 average rating, 272 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)

Guest favourite
A spacious bed is centered against a vibrant mural featuring tropical leaves and abstract shapes. Soft lighting is provided by two pendant lights on either side, accentuating the warm wooden nightstands. Neutral tones create a serene atmosphere in this inviting bedroom.
Apartment in Kahuku
4.97 out of 5 average rating, 255 reviews

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

Top guest favourite
A panoramic view from a high balcony captures the vibrant blue ocean and lush greenery below. Diamond Head's iconic profile stands prominently in the distance, framed by a clear sky dotted with fluffy clouds. Nearby residential buildings add to the scenic landscape.
Flat in Waikiki
4.99 out of 5 average rating, 116 reviews

Ocean View Sunset, Free Parking, Pool, 5m to Beach

Aloha and welcome to one of the most amazing complete remodels you will find in Waikiki - completed end of 2022. This one-of-a-kind 1 bedroom with free 1 parking stall, pool and gym boasts spectacular ocean & Diamond Head views and is only 0.2 miles (5 min walk) from Waikiki Beach and closer to endless restaurants, shopping & so much more. We would love to have you stay with us and create memories in this truly magical place that is centrally-located, well appointed, and with fabulous views!

Guest favourite
A bright living area features large sliding glass doors offering unobstructed views of the ocean. Comfortable seating is arranged around a coffee table, with a TV mounted nearby. Tropical decor and tile flooring create a relaxing atmosphere, inviting guests to enjoy the coastal scenery.
Flat in Waianae
4.95 out of 5 average rating, 118 reviews

9K Hawaiian Princess - Alii Hale Aina

Beautiful remodeled Hawaiian Princess unit on one of the best beaches on Oahu. The view is nothing less than spectacular. The condo has been remodeled with the best of everything. You will not find a better place on the island if you are looking for a beach vacation away from the crowds of Waikiki. This unit has an NUC and is permitted rental Feel free to message me (scroll to the bottom) if you cannot find availability on the calendar. I have other listings on island that may be available

Top guest favourite
A modern kitchen and living area are depicted in the image. The kitchen features sleek white cabinets and a spacious island. A stainless steel refrigerator and stove are visible. Natural light fills the area through large sliding glass doors, overlooking a green landscape.
Apartment in Kahuku
4.99 out of 5 average rating, 324 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

Top guest favourite
A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.
Apartment in Waianae
4.97 out of 5 average rating, 325 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favourite
A light-filled living area features a comfortable beige sofa adorned with decorative cushions. A coffee table is positioned on a soft area rug, with two dining chairs and a round table near a large window, offering views of the surrounding greenery.
Apartment in Kahuku
4.87 out of 5 average rating, 448 reviews

North Shore Oahu Getaway at Turtle Bay Resort

880 acres of Turtle Bay Resort while staying in our luxury condo. Our beach cottage is a perfect place to relax and unwind. Located at Kuilima Estates West in the Gold Coast "quiet corner" of the property, less car traffic. It's called the Gold Coast for a reason! Enjoy stunning views of the golf course and a peek a boo view of the ocean right from the windows of your living room. Our condo has 3 on site pools, charcoal BBQ pit, tennis courts, and basketball courts in this gated community

Top guest favourite
Home in Makaha Valley
4.96 out of 5 average rating, 167 reviews

3BR, Near Beach, Game RM, Private Spa, Pool, Gym

Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

Guest favourite
A private balcony features a small round table adorned with a colorful mosaic design and two wicker chairs. The view showcases the scenic Waikiki Beach, the shimmering ocean waves, and the lush lagoon bordered by palm trees.
Apartment in Waikiki
4.91 out of 5 average rating, 214 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Guest favourite
A dining table is placed in front of large windows, offering a view of the ocean and a palm tree swaying gently. The clear blue sky contrasts with the water's gentle waves, creating a serene atmosphere.
Apartment in Hauula
4.88 out of 5 average rating, 110 reviews

"Coconut Cottage by the Sea" Steps to the beach!

Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym, security & FREE parking!

Guest favourite
A spacious bedroom is illuminated by natural light, showcasing a beautifully designed king-size bed with crisp white linens and a soft headboard. A large flat-screen TV is mounted on a wooden accent wall. The room features a cozy seating area and direct access to the patio.
Flat in Waikiki
4.95 out of 5 average rating, 105 reviews

32F-Penthouse Pacific Monarch Studio-Ocean View

Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.

Top guest favourite
Apartment in Downtown Honolulu
4.98 out of 5 average rating, 263 reviews

Modern 1 Bedroom Condo in Downtown Honolulu

Aloha and welcome! Newly remodeled, clean and cozy 1 bedroom, 1 bathroom condo is in the heart of downtown Honolulu. Enjoy the views of the harbor and the city. We are a quick 10 min drive to beautiful Waikiki. Come explore all Oahu has to offer - surfing, swimming, snorkeling, relaxing on the beach, hiking, shopping, fine dining and more! Then unwind and relax in the comfort of the condo. We welcome you and hope you enjoy paradise at an affordable price.

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

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Avg. price€ 388€ 320€ 366€ 430€ 512€ 525€ 430€ 427€ 341€ 320€ 320€ 324
Avg. temp22°C22°C23°C24°C24°C26°C26°C27°C26°C26°C24°C23°C

Quick stats about holiday rentals with a pool in Kailua

  • Total holiday rentals

    Explore 90 holiday rentals in Kailua

  • Nightly prices starting at

    Kailua holiday rentals start at € 60 per night before taxes and fees

  • Verified guest reviews

    Over 1,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 of Kailua holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kailua rentals

  • 4.8 Average rating

    Kailua stays are highly rated by guests – averaging 4.8 out of 5!

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