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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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Superhost
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 Punaluu
4.77 out of 5 average rating, 168 reviews

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! 1 bed w/ king bed & queen bed in the living room too! Directly on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped kitchen, washer/dryer in the condo & private lanai looking out at a spectacular beach with amazing ocean views! Enjoy incredible sunrises too! Pool, gym, BBQ area & WIFI. Close to may attractions like PCC, Kualoa Ranch & More!

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, 164 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 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

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.
Condo in Waikiki
4.9 out of 5 average rating, 107 reviews

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. :-)

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.
Apartment in Waikiki
4.98 out of 5 average rating, 116 reviews

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.

Top guest favourite
Home in Makaha Valley
4.99 out of 5 average rating, 133 reviews

Beach 6 Min|BBQ|Community Pool+Gym|Peaceful+Gated

Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!

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, 343 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 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
4.88 out of 5 average rating, 273 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 with cool breezes, washer & dryer, and Split 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 and enjoy a true authentic Hawaiian experience!

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.
Condo in Kawela Bay
4.89 out of 5 average rating, 261 reviews

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.

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
4.98 out of 5 average rating, 121 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.

Superhost
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.
Condo in Waikiki
4.94 out of 5 average rating, 100 reviews

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!

Superhost
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.
Condo in Waikiki
4.88 out of 5 average rating, 233 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! There’s 2 Ilikai pool iavailable for our guests. Also accepting long term stays at special rates.

Top guest favourite
Condo in Downtown Honolulu
4.98 out of 5 average rating, 283 reviews

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.

Popular amenities for rentals with a pool near Kailua Beach

Quick stats about rentals with a pool near Kailua Beach

  • Total vacation rentals

    Explore 30 vacation rentals in Kailua Beach

  • Nightly prices starting at

    Kailua Beach vacation rentals start at $294 CAD per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Kailua Beach vacation 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!