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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 Kawela Bay
4.93 out of 5 average rating, 270 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 tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.
Guest house in Kailua
4.81 out of 5 average rating, 200 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

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.
Flat in Kawela Bay
4.9 out of 5 average rating, 250 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.
Apartment in Kawela Bay
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.
Apartment in Makaha
4.97 out of 5 average rating, 322 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.

Top guest favourite
Apartment in Kawela Bay
4.94 out of 5 average rating, 193 reviews

The Turtle Bay Signature

Come enjoy this newly updated, designer inspired, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave this tropical paradise. Everything has been updated, including hand-picked pendants that can be dimmed to suit your mood. There is a nearby pool, beach and tropical walking trails. Restaurants and shops can be found at the newly renovated Turtle Bay hotel.

Top guest favourite
The open-concept great room features a comfortable seating area with a sofa and accent chairs, complemented by a round dining table. The room is designed with large windows providing natural light and views of the surrounding tropical greenery, enhancing the indoor-outdoor flow.
Apartment in Kawela Bay
4.99 out of 5 average rating, 184 reviews

Rated Top 5% Airbnb: Privacy & Luxury @ Turtle Bay

Relax in complete privacy at your newly renovated end-unit retreat, nestled among tropical greenery and filled with high-end touches. From the spa-style bathroom to the gourmet kitchen, every detail is designed for your comfort and care. Sip fresh espresso surrounded by original art from noted local artists, South Pacific antiques, and the cool air of a powerful split A/C. Modeled after 5-star Hawaiian resort bungalows, this peaceful hideaway invites you to unwind in quiet luxury.

Guest favourite
A spacious bedroom is highlighted by a large bed with soft white bedding. Natural light enters through glass sliding doors, leading to a balcony with views of the mountains. Wooden accent walls complement the minimalist decor, and bedside tables feature small green plants.
Apartment in Waikiki
4.9 out of 5 average rating, 115 reviews

Newly Renovated | Low-Toxic Waikiki Airbnb

At Kind Legacy Properties, we understand the importance of reducing exposure to harmful chemicals, toxins, and heavy metals for optimal health. Our newly renovated 1 bed | 1 bath Low-toxic Airbnb features Organic bedding, Organic tea + coffee, along with air + water + shower filters, as well as low-toxic household and kitchen items! Enjoy the convenience of FREE parking and a short walk (0.3 miles) to the beach. Book your stay now and experience the ultimate wellness retreat!

Top guest favourite
Home in Makaha Valley
4.98 out of 5 average rating, 124 reviews

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We've got you covered with all the beach amenities you'll need to enjoy the crystal-clear waters and white sandy beaches. Whether you're looking for a romantic escape or a fun-filled family vacation, our property has everything you need to create unforgettable memories.

Guest favourite
Home in Kawela Bay
4.92 out of 5 average rating, 102 reviews

Bright stay near Turtle Bay w/ pool & BBQ grill

Welcome to your North Shore escape - a relaxed stay near Turtle Bay w/ easy beach access & resort-style perks. Settle in, unwind, & enjoy island living at your own pace: - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Shared outdoor pool (year-round), tennis & pickleball courts - Beach access + beach essentials & kayak - Private patio or balcony + BBQ grill - Kitchen, Wifi, workspace & in-unit washer/dryer - Family-friendly w/ Pack ’n play/Travel crib & toys

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.
Apartment in Kawela Bay
4.93 out of 5 average rating, 226 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.

Guest favourite
An open dining area is highlighted by a large wooden table with seating for six, complemented by natural light from sliding glass doors. The adjacent kitchen features modern appliances and a spacious island with bar seating, creating a welcoming atmosphere for gatherings.
Home in Makaha Valley
4.97 out of 5 average rating, 120 reviews

Hawaiian Pakele (escape)

Aloha and welcome to our home!! Newly built and luxuriously appointed, this beautiful 3 bedroom and 2.5 bathroom house is the ideal spot on the west side of Oahu. Located in the private gated community, with breath taking views of ocean and mountains and only a 3-min drive to the world famous Makaha beach. This is the most desirable location for families, friends and couples to escape, relax and enjoy a rejuvenating and memorable vacation!

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

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Avg. price£345£285£326£383£456£467£383£380£304£285£285£289
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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 £53 per night before taxes and fees

  • Verified guest reviews

    Over 1,540 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

    80 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!

Destinations to explore

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