Holiday rentals with a pool in Kailua

4.77 out of 5 average rating, 147 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.

Apartment 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 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.

4.9 out of 5 average rating, 124 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.

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, 250 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, 234 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, 121 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. :-)

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, 300 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, 307 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.

Apartment 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, 316 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!

4.79 out of 5 average rating, 171 reviews

A serene view of the expansive saltwater pool, framed by lush greenery and tropical plants. Outdoor furniture is arranged on the wooden deck beside the pool, overlooking the tranquil water and rock features. The ocean can be seen in the distance between the buildings.

Guest suite in Kailua

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks

Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

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.

4.99 out of 5 average rating, 106 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!

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.

4.99 out of 5 average rating, 172 reviews

Rated Top 1% 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.

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, 198 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.

Popular amenities for Kailua rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 123 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

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, 132 reviews

Large family home 5 min from beach- with pool

4.79 out of 5 average rating, 84 reviews

Home in Kailua

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

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

5 out of 5 average rating, 9 reviews

Home in Kapolei

"Piece of Paradise!" Luxurious 4-bed

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, 129 reviews

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

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.

4.95 out of 5 average rating, 152 reviews

Game Room, Near Beach, Ocean views, Gym, & Pool

A bright living room features modern furniture with a dark gray couch and two vibrant purple chairs. Natural light fills the space from large windows, framed by sheer curtains, and a piece of scenic artwork is displayed on the wall. A small coffee table holds decorative items.

4.96 out of 5 average rating, 115 reviews

Oahu Perfect Vacation •Pool, Near Beach, Sleeps 14

Apartment rentals with a pool

A modern living area features gray sofas arranged around a wooden coffee table. Natural light streams through a large window, illuminating the open layout, which connects to a kitchen and dining area in the background. A flat-screen TV is mounted on the wall.

4.91 out of 5 average rating, 159 reviews

Lovely Stay in Turtle Bay

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, 488 reviews

RusticLuxe — Go Fully Custom at Turtle Bay

The living room features a dark leather sofa with decorative pillows, positioned beside a wooden coffee table on a plush area rug. Wall art includes wooden paddles and displayed artwork. The staircase leads to the upper level, with a washer and dryer conveniently located in a nearby nook.

4.94 out of 5 average rating, 217 reviews

Turtle Bay Condo. Cozy retreat for two.

The open-concept kitchen features modern appliances, including a refrigerator, and a large island with seating for four. Natural light fills the space through sliding glass doors that lead to the lanai, showcasing a relaxing area with a tent and views of the surrounding area.

4.88 out of 5 average rating, 135 reviews

NEW*STUNNING Luxury 1BR Ocean View*Central Waikiki

The spacious bathroom features a modern vanity with dual sinks and large mirrors above. A glass shower enclosure offers a view of classic white subway tiles. Decorative accents include a wooden tray with toiletries, a rolled towel, and a flowering plant, complemented by intricate patterned flooring.

4.95 out of 5 average rating, 204 reviews

Modern Condo_Free Private On-Site Parking

4.8 out of 5 average rating, 117 reviews

A private balcony is showcased with two light blue chairs positioned around a small table. The view highlights ocean waves and lush palm trees, creating a serene backdrop. The indoor-outdoor space invites relaxation with clear skies and gentle breezes.

Apartment in Waianae

*Serendipity on the Moana! - Legal & Beachfront!*

A bright and airy studio space is highlighted by large windows offering panoramic views of the city and ocean. A king bed with light bedding is paired with a bedside table and lamp. A small dining table with two chairs is positioned beside the window.

4.91 out of 5 average rating, 244 reviews

Panoramic Ocean View/ Full Kitchen/2603A

An expansive view showcases the city skyline alongside lush greenery and a winding river. In the distance, mountains add depth to the horizon under a clear blue sky, creating a tranquil scene from the high vantage point.

4.95 out of 5 average rating, 139 reviews

Relaxing amazing Ocean and Diamond Head View

Other holiday rentals with a pool

4.89 out of 5 average rating, 210 reviews

Aerial view captures the resort complex positioned along the shoreline, featuring three distinct buildings surrounded by lush landscaping. The calm lagoon reflects the pastel colors of the sunset, with a sandy beach and rocky outcrops enhancing the coastal scenery.

Villa in Kapolei

Studio Suite Ko Olina at MARRIOTT Beach Club

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

The spacious living area features two queen beds with plush memory foam mattresses. A soft blanket is draped across the bed. The walls are adorned with a tropical design, enhancing the modern aesthetic. Large windows allow natural light to fill the room.

4.97 out of 5 average rating, 123 reviews

Amazing Central Waikiki Wonder

The living room features a spacious sectional sofa and a large 75-inch 4K smart TV mounted on the wall. A stylish kitchen island with seating is visible in the foreground, while expansive windows showcase stunning views of the Hawaiian Mountains.

4.98 out of 5 average rating, 55 reviews

17F-Beautiful & Upscale-Waikiki Beach 1BR/Parking~

The bedroom features a spacious bed with a light blue patterned coverlet, complemented by matching pillowcases. A set of three framed wall art pieces adorns the green walls. Natural light filters through the window, and a mirror reflects the calming setting.

5 out of 5 average rating, 66 reviews

Kuilima Estates West at Turtle Bay with King Bed

4.99 out of 5 average rating, 92 reviews

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

A lounge chair is positioned on a spacious balcony, overlooking a panoramic ocean view. A small side table is presented nearby, featuring two glasses and a decorative plant. The vibrant blue water and sandy beach are visible in the background, surrounded by palm trees.

5 out of 5 average rating, 60 reviews

Oceanfront Dream Home (Car & Parking Available)

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.