Holiday rentals with a pool in Kailua

4.77 out of 5 average rating, 148 reviews

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.

Condo in Hauula

"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!

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.

4.93 out of 5 average rating, 255 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.)

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.

4.98 out of 5 average rating, 238 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.

A woman stands on the spacious lanai, enjoying the ocean view framed by a full wall of windows. Comfortable outdoor furniture, including a round table and cushioned chairs, complements the serene atmosphere. Lush greenery is visible, enhancing the coastal setting.

4.96 out of 5 average rating, 125 reviews

Oceanfront Paradise (Car & Parking Available)

* Aloha! Welcome to our beachfront home with a unique design! * Enjoy incredible ocean views, a spacious lanai, a full kitchen, and modern amenities. Sip your morning coffee while watching the ocean, sailboats, surfers, or even whales. You can also watch fireworks directly from the lanai every Friday! The condo is right on Waikiki Beach. Just a short walk to the beaches, restaurants, bars, shopping centers, and more. Hawaii is our happy place. I hope it can bring you some happiness too. :-)

4.8 out of 5 average rating, 196 reviews

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.

Guesthouse in Kailua

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

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.

4.99 out of 5 average rating, 308 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.

4.97 out of 5 average rating, 314 reviews

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

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.

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.

4.91 out of 5 average rating, 322 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!

A panoramic view shows the ocean and Diamond Head from the sliding doors, framed by the open patio. The scene highlights lush greenery and the skyline of Waikiki against a bright blue sky with fluffy white clouds.

4.96 out of 5 average rating, 256 reviews

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

Location, Location, Location! Stunning penthouse just a block from Waikiki Beach. Top-floor at Waikiki Grand Hotel—2 studios combined into 1 spacious, renovated retreat! Enjoy breathtaking ocean & Diamond Head views from your suite. Sunrise & sunset magic awaits just outside on the sundeck. Kitchenette + beach gear included. FREE PARKING, though a car isn’t needed—walk to beach, shops & nightlife! Ideal for families, business, or solo stays. LEGAL VACATION RENTAL All Fees INCLUDED in rate

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.

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.

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.

4.9 out of 5 average rating, 168 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!

Aerial view of Waikiki Beach, showcasing the clear turquoise water and soft sandy shores. The natural jetty is visible, providing a calm swimming area, while beachgoers and sun loungers dot the coastline. Lush palm trees frame the scene, with buildings lining the shore in the background.

4.95 out of 5 average rating, 213 reviews

Spectacular Views - Spacious 2BR Waikiki Penthouse

Enjoy this once in a lifetime ocean view in the heart of Waikiki. This spacious 2 bedroom, 2 bathroom penthouse provides all the necessities for the perfect Hawaiian holiday. Located across the street from the world-famous Waikiki Beach, you have easy walking access to restaurants, shops and entertainment. This picturesque penthouse offers new appliances, comfortable beds, in-house laundry, A/C, a lanai with a spectacular view and more. Your dream vacation awaits!

Popular amenities for Kailua rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 128 reviews

A serene bedroom features a spacious bed with crisp white linens, complemented by soft, natural textures. Large windows showcase ocean views, while two woven light fixtures add warmth. A dresser provides additional storage, and a neutral rug enhances the calming atmosphere.

Home in Waikiki

Waikiki Gem, Stunning Ocean View, Parking Included

Superhost

The spacious living area features large windows that provide views of the surrounding hills and natural light. A gray sofa is accented with yellow and white pillows, while a coffee table with decorative items is centered on a plush area rug. A modern lamp and potted plant add warmth to the space.

4.92 out of 5 average rating, 65 reviews

Le'ale'a by AvantStay | Ocean + Mountain Views!

4.99 out of 5 average rating, 134 reviews

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

A modern living area is furnished with a sectional sofa, accent chairs, and a coffee table. A spacious dining table is surrounded by white chairs. A ceiling fan and artwork decorate the room, while natural light streams in through the windows.

4.94 out of 5 average rating, 133 reviews

Large family home 5 min from beach- with pool

4.92 out of 5 average rating, 130 reviews

Home in Kahuku

Golf Course Front Condo in Kahuku

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.

4.97 out of 5 average rating, 90 reviews

Makaha Hale - Serene 3 BR Home

4.96 out of 5 average rating, 121 reviews

Family Ocean Oasis, Hot Tub, 5 min drive to beach

Superhost

An aerial view captures a sandy beach stretching along the coast, bordered by clear turquoise waters. Colorful umbrellas dot the beach, while small boats can be seen in the water. Lush green hills rise in the background, complementing the scenic landscape.

4.89 out of 5 average rating, 131 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

Condo rentals with a pool

An open living space showcases a dining area with a circular table and metal chairs, surrounded by natural wood accents. A large wall art piece features a world map. A sliding glass door leads to a private lanai offering views of the golf course.

4.92 out of 5 average rating, 491 reviews

RusticLuxe — Go Fully Custom at Turtle Bay

A spacious studio unit features a kitchenette with modern appliances and a dining table. A large window offers a sweeping view of the ocean, bringing natural light into the room. The bed is neatly made with a light blue blanket, fostering a serene atmosphere.

4.85 out of 5 average rating, 232 reviews

Free Parking/Ocean View/Steps to Beach & Mall 33F

4.94 out of 5 average rating, 179 reviews

A spacious living area is highlighted by a large flat-screen TV and a comfortable sofa adorned with decorative cushions. The open layout connects to a dining area featuring a table with several chairs. Scenic views of the lagoon and coastline are visible through expansive sliding glass doors.

Condo in Kapolei

Ko Olina Beach! Largest villa w/2 Masters, 03/15

An expansive balcony is visible, featuring a table and two chairs, overlooking a stunning ocean view. The azure waters and palm trees create a serene backdrop. Floor-to-ceiling glass doors provide natural light and seamless access to the outdoor space from the interior.

4.96 out of 5 average rating, 117 reviews

Waikiki Beachfront Home with Ocean and Beach View

The kitchen features modern cabinetry and stainless steel appliances, including a refrigerator and stove. A spacious island with three bar stools offers additional seating. Soft lighting from pendant lamps enhances the room's functional design, while natural light fills the space through nearby windows.

4.87 out of 5 average rating, 133 reviews

Hale Koa (Newly updated condo with split AC)

4.92 out of 5 average rating, 188 reviews

A private balcony offers a clear view of the skyline and coastline, showcasing the vibrant city below. The space includes a small round table with two chairs, providing a relaxing spot to enjoy the panoramic scenery and the bright blue sky.

Condo in Ala Moana

Alamoana Hotel 29FL Studio City&Partial Ocean View

A light-filled living area is presented with a cozy white sofa, accented by decorative pillows featuring ocean-themed designs. Two rattan chairs flank a small glass table, while natural light filters through flowing sheer curtains. A potted plant brings a touch of greenery to the space.

4.84 out of 5 average rating, 403 reviews

Luxe Loft at Turtle Bay

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.

4.9 out of 5 average rating, 104 reviews

Newly Renovated | Low-Toxic Waikiki Airbnb

Other holiday rentals with a pool

An open studio layout showcases a spacious bedroom area with a king-size bed and a cozy seating arrangement featuring a dark sofa. Large glass doors frame stunning ocean and harbor views, while a TV is positioned for easy viewing from the living area.

4.95 out of 5 average rating, 66 reviews

Beautiful OceanView&Sunset @IlikaiResort w/Parking

A serene bedroom features a spacious bed with natural light streaming in from a large window. A desk with a laptop is positioned beside a stylish chair, while a potted leafy plant adds a touch of greenery. The stunning ocean view enhances the calming ambiance.

4.97 out of 5 average rating, 34 reviews

MOANA Suite • Panoramic Ocean View • FREE Parking

A panoramic view showcases the calm blue ocean meeting the clear sky. Lush palm trees line the beach, and gentle waves lap at the shore, creating a serene coastal landscape that invites relaxation.

4.95 out of 5 average rating, 65 reviews

Luxury Oceanfront Waikiki Beach Tower w Ocean View

A view of the shoreline featuring a mountainous landscape, partially covered by green vegetation. The calm water reflects the bright blue sky, with a few white clouds gently drifting overhead. The natural scenery suggests a peaceful coastal environment.

4.91 out of 5 average rating, 75 reviews

Peaceful cozy comfortable apartment

A spacious living area features a king bed with light linens, complemented by a backdrop of ocean views through large glass doors. A contemporary sofa and bar seating with stools create a relaxed atmosphere, with a smart TV providing entertainment options.

5 out of 5 average rating, 27 reviews

20F-High Floor Ocean View-Ilikai-1BR-Waikiki Beach

Superhost

A spacious living room features a large modular sectional sofa, thoughtfully arranged for comfort. Floor-to-ceiling windows provide abundant natural light and showcase panoramic views of the ocean. A coffee table sits in the center, with decorative items adding to the modern design.

4.85 out of 5 average rating, 55 reviews

37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~

4.99 out of 5 average rating, 98 reviews

Ocean View Sunset, Free Parking, Pool, 5m to Beach

The living area features a large sectional sofa with soft cushions, complemented by a round coffee table. Natural light floods in through expansive floor-to-ceiling windows, revealing stunning mountain views. A dining table for six can also be seen, providing an inviting space for meals.