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 private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.
Apartment in Hauula
4.77 out of 5 average rating, 148 reviews

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! This 1 large bedroom has a new king bed, and there is a bed in the living room as well. Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped remodeled kitchen, washer/dryer & private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

Superhost
A spacious living area features large windows offering panoramic ocean views. Modern furnishings include a soft sofa adorned with decorative pillows, a stylish armchair, and a wooden dining table. Natural light brightens the room, enhancing the fresh coastal ambiance.
Apartment in Waikiki
4.9 out of 5 average rating, 126 reviews

32nd Floor Penthouse. 3min walk to Waikiki Beach

Welcome to HaleHinano Penthouse, Waikiki Beach. Enjoy this rarely find 1BR Penthouse on the 32nd floor with panoramic ocean views of the crisp Hawaiian waters. This condo is fully renovated with modern furnishings and decor. Just a few steps away, you’ll be at beach fronts of Waikiki beach. You’ll be surrounded with local favorite fine dining, shopping plazas. -In unit washer and dryer. -Top roof Pool, Jacuzzi, BBQ -3 min walk to the Waikiki beach. -$35/day parking attached to the building.

Guest favourite
A private lanai is shown, featuring a sleek outdoor dining table with two lanterns. The view captures the ocean with sailboats in the distance, alongside lush greenery and palm trees, creating a serene backdrop against the clear blue sky.
Apartment in Waikiki
4.9 out of 5 average rating, 147 reviews

Ocean View w/ 2 private balconies; Steps to Beach

BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!

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
4.98 out of 5 average rating, 237 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
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
4.8 out of 5 average rating, 196 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 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, 305 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.

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, 313 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 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.
Apartment in Kahuku
4.91 out of 5 average rating, 320 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 open-concept living area showcases a modern kitchen with stainless steel appliances and stylish cabinetry. A spacious bed is positioned near a cozy seating area, accompanied by a wooden coffee table. Three pendant lights illuminate the bar-style seating, enhancing the inviting ambiance.
Apartment in Waikiki
4.99 out of 5 average rating, 109 reviews

Modern Condo in the Heart of Waikiki Free Parking

Escape to paradise with this NEW, stylish condo in the heart of Waikiki! Recently renovated and located in the Marine Surf Waikiki building, you're just steps away from the best restaurants, shopping, and Waikiki Beach. Enjoy the ultimate island lifestyle with all the modern amenities you need for an unforgettable stay. Whether you're looking to catch some waves, soak up the sun, or simply relax and unwind, this condo has everything you need. Book now and experience the best of Waikiki!

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
4.95 out of 5 average rating, 154 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
4.9 out of 5 average rating, 202 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
An aerial view captures the surrounding landscape near Turtle Bay, showcasing the proximity to the ocean. The layout includes green lawns, tennis courts, and the marked unit within a cluster of residences, all set against a backdrop of blue waters and a clear sky.
Apartment in Kahuku
4.9 out of 5 average rating, 167 reviews

North Shore Getaway - Newly renovated!

Enjoy the amazing experience of staying at Turtle Bay without resort pricing! Our condo has all the amenities you need (fully stocked kitchen, comfortable king bed with air conditioning, washer and dryer). Enjoy our two heated swimming pools, tennis courts, pickle ball courts, and charcoal BBQ. We are just a 5 minute walk from the beach. We are located on the ground floor with a beautiful lanai to enjoy a relaxing cup of coffee while the kiddos are free to run around!

Popular amenities for Kailua rentals with a pool

When is the best time to visit Kailua?

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Avg. price$585 SGD$482 SGD$551 SGD$648 SGD$771 SGD$790 SGD$648 SGD$643 SGD$514 SGD$643 SGD$608 SGD$661 SGD
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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 $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,530 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

  • 4.9 Average rating

    Kailua stays are highly rated by guests – averaging 4.9 out of 5!

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