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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 80 holiday rentals in Kailua

  • Nightly prices starting at

    Kailua holiday rentals start at $121 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,430 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

    80 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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Guest favourite
A modern open-concept living space features a comfortable sofa and a decorative coffee table. The dining area includes a sleek kitchen island with bar stools. Natural light brightens the room through a large decorative mirror, while stylish accents and greenery enhance the coastal aesthetic.
Condo in Kawela Bay
4.97 out of 5 average rating, 205 reviews

Honu Hideout at Turtle Bay

Come escape to Honu Hideout on the exclusive North Shore of Oahu, and enjoy this newly renovated ground floor unit situated just a short walk away from the iconic Turtle Bay Resort and the most breathtaking and secluded beaches on Oahu. Far away from the hustle and bustle of Honolulu, this unit offers the peacefulness of the country and the proximity to infamous attractions for the vacation of your dreams. Relax and restore or adventure and explore, you choose, all within minutes of your door.

Top 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, 270 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
Apartment in Kawela Bay
4.98 out of 5 average rating, 325 reviews

N Shore Turtle Bay Kuilima Condo Getaway! Reviews!

Ritz Carlton without the price, this vacation condo is just that! Enjoy resort convenience w/o the resort price! Quiet and tucked against the golf course, we have a beautiful pool & tennis court on site. Just a few minutes walk to Turtle Bay Ritz , which has great beaches to snorkel and swim, restaurants,bars, 2 golf courses, the Arnold Palmer &George Fazio, biking/walking trials. Sunset beach, Waimea Bay, Haleiwa, Banzai Pipeline, Polynesian Culture Center, world famous food trucks all near

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, 109 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!

Guest favourite
Condo in Kawela Bay
4.91 out of 5 average rating, 185 reviews

Turtle Bay Condo Lilinoe

Ground floor end unit, located on the 18th hole of the world re-nowned Turtle Bay resort! King sized bed in bedroom, 1 queen Murphy bed and 1 queen sofa bed in living room. AC in both bedroom and living room. Screened-in lanai. Tennis courts, pool and bbq grills. Beach is 5 minutes walking distance. Short drive away from prime spots (sunset beach, pipeline, shark’s cove, Waimea) shopping, and food. Our condo is a legal short-term rental. Ask me about my other properties for larger parties.

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
4.89 out of 5 average rating, 266 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 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, 338 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, 355 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
The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.
Cottage in North Shore
4.88 out of 5 average rating, 156 reviews

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

Top Guest favourite
The exterior of the cottage showcases a modern design with a welcoming front entrance and large windows. A two-car garage is visible on the right, while stunning mountain scenery frames the background. The sky is adorned with soft hues of pink and orange as the sun sets.
Cottage in Waianae
4.97 out of 5 average rating, 116 reviews

Cottage Nene - Luxury Home by Beaches & Mountains

Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.

Guest favourite
A private hot tub is positioned in the foreground, surrounded by lush tropical landscaping. The two-story home stands in the background, framed by picturesque mountain views. The outdoor space offers a well-maintained lawn and a patio area, inviting relaxation in a tranquil setting.
Home in Makaha Valley
4.94 out of 5 average rating, 179 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
A bright living area is accented by a large wall mural depicting surfboards on turquoise waters. A comfortable white sofa is adorned with plush pillows and a soft throw. A natural fiber rug covers the floor, complemented by a round lamp and a stylish coffee table.
Condo in Kawela Bay
4.89 out of 5 average rating, 379 reviews

SEArider ONE at Turtle Bay

~ You just found your Base Camp to explore the North Shore of Oahu ~ Our condo has just been completely remodeled and redecorated with two brand new bathrooms. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the ocean. Enjoy the resort amenities of Turtle Bay coupled with the comfort of condo living. Health and comfort are top priority. We pride ourselves on a clean home and have implemented additional measures for sanitization.

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$867 NZD$650 NZD$607 NZD$874 NZD$1,040 NZD$1,066 NZD$874 NZD$867 NZD$693 NZD$650 NZD$650 NZD$659 NZD
Avg. temp22°C22°C23°C24°C24°C26°C26°C27°C26°C26°C24°C23°C

Destinations to explore

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