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Home rentals with a pool near Kailua Beach

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Top-rated rentals with a pool near Kailua Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

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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

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

Hawaii’s Best Kept Secret! The cottage is next to sandy coves, driftwood, shells, and Polo ponies in forested pastures. The ocean is excellent for snorkeling and fishing; there are 2 surf spots, & world-class windsurfing within 2 mile. Mountains behind us offer good hiking trails. The Colony has a nice pool, and a Pickle Ball court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021. Note: We have NO Air Conditioner, 3 ceiling fans, 2 desk fans & ocean

4.88 out of 5 average rating, 165 reviews
Guest favourite
An inviting balcony space is visible, featuring a round, cushioned chair beside a small, white table. The ocean stretches out in the background, framed by palm trees and gentle waves lapping against the shore, creating a serene coastal view.
Apartment in Waikiki

Dreamy Beachfront Home (Car & Parking Available)

* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls and more. Every time I come to Hawaii, I am happy. I hope our place can bring you happiness too. :-)

4.89 out of 5 average rating, 109 reviews
Top guest favourite
A modern studio space features a queen-sized bed with a soft aqua throw. Light wood accents and a wooden feature wall complement the decor. An open kitchen area is equipped with appliances, including a blue stove, while a small dining table with two stools is visible nearby.
Flat in Waikiki

Luxury Waikiki Condo w/ Retro Charm & FREE Parking

Welcome to this renovated 20th-floor condo in the iconic Marine Surf, a former 1960s Waikiki hotel. Enjoy vintage charm with modern luxury, including a partial ocean view, FREE underground parking, ultra-fast 1-gigabit internet, AC and a 65" smart TV with Apple TV. Relax in the pool or explore nearby world-class shopping, dining & beaches. With a queen bed and sofa bed, it’s perfect for couples or families. Reserve your slice of paradise today and discover the essence of Waikiki’s island luxury.

4.98 out of 5 average rating, 120 reviews
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

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!

4.97 out of 5 average rating, 114 reviews
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 Makaha

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.

4.97 out of 5 average rating, 344 reviews
Guest favourite
An open layout features a kitchen with modern appliances and a dining area, complemented by bar seating. The loft area with a visible sleeping space is showcased above, while natural light floods through large windows, enhancing the airy atmosphere of the living space.
Apartment in Kawela Bay

Legal STR: Aloha at Turtle Bay w/ Loft

TMK #570010270107 STR license # 51 Quiet upstairs unit with loft. Cooling trade breezes drift from the lanai through to the master bedroom. Walk to golf, restaurants and the beaches at the Ritz Carlton Oahu at Turtle Bay. 2 swimming pools, tennis and pickleball on site. Has beach toys and gear, tennis and pickleball rackets. WiFi, cable and Smart TV’s. Drive to North Shore beaches and local shopping. Gated, 24 hour security. One parking spot included. 2nd parking spot with permit.

4.89 out of 5 average rating, 263 reviews
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

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.

4.98 out of 5 average rating, 126 reviews
Guest favourite
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.
Apartment in Waikiki

Beautiful OceanView&Sunset @IlikaiResort w/Parking

🌴 BRAND NEW LISTING. NO RESORT FEES. FREE PARKING! 🌴 ✨ This ocean front condo is located at the iconic Ilikai Hotel & Luxury Suites. Your perfect getaway on the 9th floor offering beautiful ocean, sunset, & harbor views everyday! 💎 Immerse yourself in the beauty of Hawaii with just steps away from the pristine beach & lagoon. 🏝️ This inviting studio condo provides an exceptional experience surrounded by a vibrant neighborhood filled with shops, eateries, & fun filled activities!

4.94 out of 5 average rating, 103 reviews
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

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.

4.89 out of 5 average rating, 235 reviews
Top guest favourite
The exterior of a two-story vacation home is framed by lush green lawn and surrounded by landscaped areas. Soft lighting highlights the property against a dramatic sunset backdrop, with colorful clouds above the nearby mountains, enhancing the tranquil setting.
Home in Waianae

Beach 5 Min|Community Pool+Gym|Gated|Mountain View

This four-bedroom retreat in the gated Mauna Olu Estates blends mountain views with local Hawaii design touches - a custom wood bar table and mural in the dining room. It sleeps up to 10 across four bedrooms - a king suite, two queens, and a flexible fourth room with a full bed, trundle, and sleeper sofa. Guests get community pool and gym access plus a private, fenced backyard for grilling. It's an easy fit for a family reunion or multiple families traveling together.

4.99 out of 5 average rating, 129 reviews
Guest favourite
A spacious bedroom is illuminated by natural light, showcasing a beautifully designed king-size bed with crisp white linens and a soft headboard. A large flat-screen TV is mounted on a wooden accent wall. The room features a cozy seating area and direct access to the patio.
Flat in Waikiki

32F-Penthouse Pacific Monarch Studio-Ocean View

Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.

4.96 out of 5 average rating, 134 reviews
Top guest favourite
Apartment in Downtown Honolulu

Modern 1 Bedroom Condo in Downtown Honolulu

Aloha and welcome! Newly remodeled, clean and cozy 1 bedroom, 1 bathroom condo is in the heart of downtown Honolulu. Enjoy the views of the harbor and the city. We are a quick 10 min drive to beautiful Waikiki. Come explore all Oahu has to offer - surfing, swimming, snorkeling, relaxing on the beach, hiking, shopping, fine dining and more! Then unwind and relax in the comfort of the condo. We welcome you and hope you enjoy paradise at an affordable price.

4.98 out of 5 average rating, 285 reviews

Popular amenities for rentals with a pool near Kailua Beach

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
Home in Waianae

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

4.95 out of 5 average rating, 150 reviews
Guest favourite
An open dining area is highlighted by a large wooden table with seating for six, complemented by natural light from sliding glass doors. The adjacent kitchen features modern appliances and a spacious island with bar seating, creating a welcoming atmosphere for gatherings.
Home in Waianae

Hawaiian Pakele (escape)

4.96 out of 5 average rating, 138 reviews
Top guest favourite
Home in Kawela Bay

Condo near Turtle Bay w/pool, beach & BBQ

4.92 out of 5 average rating, 119 reviews
Guest favourite
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

4.97 out of 5 average rating, 149 reviews
Guest favourite
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.
Home in Waianae

Large family home 5 min from beach- with pool

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

Private SPA, Sleep 12, Beach 5 min

4.94 out of 5 average rating, 156 reviews
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.
Home in Makaha Valley

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

4.9 out of 5 average rating, 158 reviews
Superhost
Home in Kailua

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

4.71 out of 5 average rating, 95 reviews

Apartment rentals with a pool

Guest favourite
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

32nd FL Penthouse, Ocean View, 3 min walk to Beach

4.91 out of 5 average rating, 152 reviews
Superhost
Apartment in Downtown Honolulu

2BR+Den Downtown w/ Ocean Views + Free Parking

4.81 out of 5 average rating, 138 reviews
Top guest favourite
Apartment in Downtown Honolulu

Luxury Condo with Ocean Views & FREE Parking!

4.96 out of 5 average rating, 182 reviews
Top guest favourite
A serene lanai features two turquoise lounge chairs beside a small round table. A view of the marina and ocean is visible in the background, showcasing boats and a clear blue sky. A decorative pineapple sits atop the table, accompanied by two cups.
Apartment in Waikiki

Waikiki Ocean & Sunset View Condo-free parking

4.96 out of 5 average rating, 330 reviews
Guest favourite
Apartment in Waikiki

Ocean & Marina View + FREE Parking | Ilikai Marina

4.94 out of 5 average rating, 194 reviews
Top guest favourite
A bright studio apartment features a spacious bed adorned with layered linens and decorative pillows. Artwork depicting tropical scenes hangs on the walls. A cozy seating area is seen beside the bed, illuminated by natural light from large glass doors leading to a balcony.
Apartment in Waikiki

Free Parking • Waikiki • King Bed

4.94 out of 5 average rating, 156 reviews
Top guest favourite
A dining table is set for a meal, featuring plates, glasses, and a small vase with flowers. Floor-to-ceiling windows offer sweeping views of the ocean and Waikiki skyline under a bright blue sky with scattered clouds.
Apartment in Waikiki

2Bed/2Bath Waikiki Corner Penthouse & Ocean Views

4.89 out of 5 average rating, 217 reviews
Top guest favourite
A bright bedroom is furnished with a spacious bed dressed in white linens and a light grey quilt. Two bedside lamps are positioned beside the bed, and a large mirror reflects the natural light. A seating area with a blue love seat is visible, along with a balcony view.
Apartment in Waikiki

Renovated Studio w/Free Parking | Walk to Beach

4.96 out of 5 average rating, 171 reviews

Other holiday rentals with a pool

Top guest favourite
A balcony view features a small round table set for breakfast, with fresh fruit and pastries arranged on plates. The ocean can be seen in the distance, along with tall buildings of the Honolulu skyline. Natural light brightens the space.
Flat in Waikiki

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen

4.95 out of 5 average rating, 125 reviews
Top guest favourite
Flat in Kawela Bay

37 West 1 Bedroom + Murphy Bed TA-104-613-6320-01

4.98 out of 5 average rating, 120 reviews
Guest favourite
A spacious living area features a king size bed with fresh linens, complemented by two boucle fabric chairs and a round coffee table. Natural light filters through a nearby window, highlighting the modern wood accent wall and a decorative wall clock.
Flat in Waikiki

39FL-Chic Modern in Waikiki-Upgraded King Studio

4.95 out of 5 average rating, 139 reviews
Guest favourite
A serene pathway leads toward the cottage, bordered by lush greenery and a manicured lawn. The ocean glistens in the distance under a bright blue sky, with a palm tree gently swaying nearby. Large windows of the cottage offer views of the tranquil waters.
Cottage in North Shore

Island Jewel, North Shore Bliss

4.99 out of 5 average rating, 95 reviews
Superhost
A modern bathroom is showcased with a deep soaking tub positioned next to large windows, providing panoramic views of the sunset over the ocean. Natural stone accents are featured throughout, while a decorative vase with flowers adds a touch of elegance.
Apartment in Waikiki

(Golden Week) Nr beach! Imperial Resort

4.93 out of 5 average rating, 40 reviews
Top guest favourite
Flat in Waikiki

Wake Up to Ocean Views! 2queen Apt w/ Free Parking

4.97 out of 5 average rating, 39 reviews
Guest favourite
A spacious living area features a comfortable gray sofa with decorative pillows, accompanied by a wooden coffee table. Two pieces of artwork hang on the wall above, and the kitchen is located in the background, showcasing modern cabinetry and appliances. Natural light fills the room, enhancing the hardwood flooring.
Flat in Waikiki

Honu Hale Waikiki: 2BDR Spacious Panoramic View

4.83 out of 5 average rating, 46 reviews
Guest favourite
Flat in Waikiki

Beautiful Ilikai Condo with City and Ocean Views

5.0 out of 5 average rating, 6 reviews

Quick stats about rentals with a pool near Kailua Beach

  • Total holiday rentals

    Explore 30 holiday rentals in Kailua Beach

  • Nightly prices starting at

    Kailua Beach holiday rentals start at £159 per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Kailua Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kailua Beach rentals

  • 4.9 Average rating

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