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Holiday rentals with a pool in Kailua

Find and book unique homes with a pool on Airbnb

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 $120 NZD 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!

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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Top Guest favourite
The beachfront property is surrounded by lush greenery and palm trees, displaying multiple levels of residential units. The sandy beach extends to the clear blue waters, with mountain views in the background under a partly cloudy sky.
Condo in Punaluu
4.91 out of 5 average rating, 293 reviews

Secluded White Sandy beach just 30 steps away

Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

Guest favourite
Condo in Kawela Bay
4.86 out of 5 average rating, 285 reviews

The Sunrise Hale at Turtle Bay - 1bedroom/2bath

Spacious, Comfortable, Clean... Look no further for your Base Camp to explore the North Shore of Oahu! This bright and airy sunrise condo is located in a gated community on the grounds of Turtle Bay Resort, allowing you to enjoy the grounds for a fraction of the price. You are within walking distance to secluded beaches, complex pools, running trails, horseback riding, surf, golf and more! The unit has been recently renovated (Flooring, bathrooms, kitchen)Come and enjoy the North Shore of Oahu

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 Kawela Bay
4.97 out of 5 average rating, 261 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.

Guest favourite
The living area is characterized by high ceilings and natural light streaming through large windows. A comfortable gray sofa is accompanied by wooden chairs and tables, creating a welcoming gathering space. A neutral rug adds warmth, while tropical plants contribute to the serene atmosphere.
Home in Waianae
4.97 out of 5 average rating, 104 reviews

Makaha Hale - Serene 3 BR Home

Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

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 Kawela Bay
4.9 out of 5 average rating, 258 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 Kawela Bay
4.99 out of 5 average rating, 332 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 Makaha
4.97 out of 5 average rating, 330 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
A modern living space is arranged with a comfortable sofa and a sleek coffee table. A large wall-mounted TV displays a marine scene. The kitchen area features white cabinetry and bar stools, while light wood flooring complements the decor. Natural light highlights the room's openness.
Condo in Kawela Bay
4.91 out of 5 average rating, 347 reviews

NEWLY RENOVATED (2021) Turtle Bay Haven!

NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

Top Guest favourite
Home in Waianae
4.98 out of 5 average rating, 155 reviews

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

Escape to paradise in this brand new vacation rental located in the secluded Makaha Valley. Just a short drive away from some of the world's most beautiful beaches, enjoy endless opportunities for hiking, golfing, and soaking up the sun. Surrounded by lush mountains and pristine nature, this rental offers the perfect retreat from the hustle and bustle of everyday life. Take in the breathtaking ocean and mountain views and create unforgettable memories in this ultimate tropical getaway.

Guest favourite
Condo in Makaha
4.97 out of 5 average rating, 152 reviews

Beachfront/Oceanfront with Tennis/Pool/Jacuzzi

BEACHFRONT. Highly upgraded, completely renovated and sparkling clean. Direct oceanfront views! Tastefully done with state of the art appliances, teak wood cabinets and the finest touches. Per new "Honolulu County laws", we may only book "one guest rental" per 30 day period as the condo does not operate as "transient quarters". Our calendar is not always up-to-date. Please contact us if you have any questions. Aloha! TAT#: TA-186-939-8016-01 GET#: W-08805160-01

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.
Condo in Waikiki
4.91 out of 5 average rating, 221 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! There’s 2 Ilikai pool iavailable 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.
Condo in Punaluu
4.88 out of 5 average rating, 115 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.

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$858 NZD$643 NZD$600 NZD$864 NZD$1,029 NZD$1,055 NZD$864 NZD$858 NZD$686 NZD$643 NZD$643 NZD$652 NZD
Avg. temp22°C22°C23°C24°C24°C26°C26°C27°C26°C26°C24°C23°C

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Kailua
  6. Rentals with pools