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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.
Condo 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.
Condo in Kahuku
4.97 out of 5 average rating, 251 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
Condo in Kahuku
4.93 out of 5 average rating, 151 reviews

North Shore Turtle Bay Renovated 2Bd/2Ba + Loft

Aloha and welcome to our spacious and beautifully renovated North Shore Turtle Bay Resort 2 Bedroom condo that includes an additional 3rd loft room + 2 bathrooms. Directly outside the living room is a large manicured grassy lawn and the Fazio Golf Course. This gated condo is a short walk to the 5 Star Ritz Carlton Turtle Bay and all of its amenities, Lei Lei's Bar & Grill, Roy's Beach House, and a beautiful white sandy beach. Swimming pool and tennis courts on site! Welcome home to paradise!

Top Guest favourite
A two-story building is framed by lush greenery and large windows. A white staircase leads to the upper level, while balconies are visible. The exterior showcases a light-colored facade that blends with the natural surroundings, creating a serene residential setting.
Apartment in Kahuku
4.9 out of 5 average rating, 252 reviews

Turtle Bay Corner Condo With A Fairway View!

Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th w/cool breezes, new washer & dryer, and A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax there and enjoy a true authentic Hawaiian experience!

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.
Condo in Kahuku
4.99 out of 5 average rating, 320 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.
Condo in Waianae
4.97 out of 5 average rating, 324 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.

Superhost
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.
Condo in Kahuku
4.87 out of 5 average rating, 446 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, 166 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!

Top Guest favourite
Condo in Downtown Honolulu
4.98 out of 5 average rating, 260 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.

Guest favourite
A modern kitchen is featured with light wood cabinetry and natural stone countertops. Three rattan bar stools are positioned at the breakfast bar. Pendant lights with woven shades hang above. Fresh greenery is placed on the counter, enhancing the spacious and airy feel of the room.
Condo in Kahuku
4.93 out of 5 average rating, 227 reviews

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

Top Guest favourite
An ocean view from a balcony captures the landscape of palm trees gracefully swaying beside a sandy beach. The calm blue ocean stretches toward the horizon, blending seamlessly with the sky. Amenities such as pools and lush greenery are visible in the foreground.
Villa in Ko Olina
4.97 out of 5 average rating, 214 reviews

Ko Olina Oceanfront | Disney | NextAvail 4/27

April 18th and April 25th, are our next available dates in our upscale, homeowner-managed 2-bedroom villa at Beach Villas at Ko Olina, steps from Disney’s Aulani (not affiliated). Enjoy boutique hotel luxury with unobstructed ocean views from our two ocean facing lanais, relaxed beachy style, and easy walks to the beach bar, restaurants, shops, golf, marina, and luau. High-end Wolf/Sub-Zero, Sonos, LG OLED, and new Miele appliances elevate your stay.

Guest favourite
Home in Kahuku
4.92 out of 5 average rating, 104 reviews

Cozy condo w/Turtle Bay, pool & beach

Experience laid‑back North Shore living just steps from Turtle Bay and the beach. Relax in a gated community with resort‑style perks and island breezes. - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Shared outdoor pool (year‑round) – tennis & pickleball courts - Beach access w/ beach essentials & kayak - Private patio/balcony w/ BBQ grill - Kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly – Pack ’n play, toys & board games

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$641 AUD$528 AUD$604 AUD$710 AUD$845 AUD$866 AUD$710 AUD$704 AUD$563 AUD$528 AUD$528 AUD$535 AUD
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 $99 AUD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Kailua holiday rentals include Wi-Fi 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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