
Home rentals with a pool near Kailua Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Kailua Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

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, 164 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!
4.76 out of 5 average rating, 169 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.
4.98 out of 5 average rating, 116 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. :-)
4.9 out of 5 average rating, 107 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!
4.92 out of 5 average rating, 177 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.
4.97 out of 5 average rating, 344 reviews
38th FLR- Luxury King Boutique Studio 1000 Cranes
Welcome to our luxurious Hawaiian retreat on the stunning island of Oahu. This beautifully-appointed Airbnb offers an unforgettable vacation experience in one of the most sought-after destinations in the world. Located in a prime location on the island, our Airbnb boasts breathtaking ocean views, pristine beaches, and a wealth of local attractions and activities. The property features exquisite furnishings, upscale amenities, and elegant touches that create a serene and relaxing ambiance.
4.95 out of 5 average rating, 175 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!
4.94 out of 5 average rating, 101 reviews
39FL-Chic Modern in Waikiki-Upgraded King Studio
With high-end finishes and a newly renovated interior, this studio in Waikiki is picture-perfect. Located on the 39th floor, it boasts partial ocean views and views of the Waikiki skyline. The building is surrounded by amazing dining and shopping options. The world-famous Waikiki beach is only a few minutes' walk away. Whether you're traveling as a couple or a small family, this unique experience is perfect for you. You'll feel right at home with all the essential amenities provided.
4.95 out of 5 average rating, 137 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.
4.88 out of 5 average rating, 234 reviews
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, 131 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.
4.98 out of 5 average rating, 283 reviewsPopular amenities for rentals with a pool near Kailua Beach
House rentals with a pool

Ocean Views|Game Room|Beach 6 Min|Fruit Trees|BBQ
4.94 out of 5 average rating, 187 reviews
Hawaiian Pakele (escape)
4.96 out of 5 average rating, 138 reviews
Makaha Hale - Serene 3 BR Home
4.97 out of 5 average rating, 114 reviews
Condo near Turtle Bay w/pool, beach & BBQ
4.93 out of 5 average rating, 116 reviews
Waikiki Gem, Stunning Ocean View, Parking Included
4.97 out of 5 average rating, 148 reviews
Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!
4.95 out of 5 average rating, 148 reviews
Private SPA, Sleep 12, Beach 5 min
4.94 out of 5 average rating, 155 reviews
Large family home 5 min from beach- with pool
4.95 out of 5 average rating, 153 reviewsCondo rentals with a pool

Premier Diamond Head & Ocean Views 1BR Suite
4.98 out of 5 average rating, 177 reviews
♥ North Shore Paradise at Turtle Bay ♥
4.94 out of 5 average rating, 249 reviews
Sweeping Ocean Views, Free Parking, Beach, Mall
4.81 out of 5 average rating, 161 reviews
SEArider TWO at Turtle Bay
4.94 out of 5 average rating, 291 reviews
Legal STR: Aloha at Turtle Bay w/ Loft
4.89 out of 5 average rating, 262 reviews
Alamoana Hotel 29FL Studio City&Partial Ocean View
4.92 out of 5 average rating, 223 reviews
Panoramic Ocean View/ Full Kitchen/2603A
4.91 out of 5 average rating, 290 reviews
Oceanfront Home (Beautiful Sunset View Every Day)
4.97 out of 5 average rating, 226 reviewsOther vacation rentals with a pool

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen
4.95 out of 5 average rating, 122 reviews
Cottage Nene - Luxury Home by Beaches & Mountains
4.98 out of 5 average rating, 121 reviews
33F-High Floor Studio w/Diamond Head & Ocean Views
4.94 out of 5 average rating, 114 reviews
43FL-Modern High-FL Studio w/Ocean & City Views
4.95 out of 5 average rating, 115 reviews
Island Jewel, North Shore Bliss
5.0 out of 5 average rating, 92 reviews
(Golden Week) Nr beach! Imperial Resort
4.93 out of 5 average rating, 40 reviews
Wake Up to Ocean Views! 2queen Apt w/ Free Parking
4.97 out of 5 average rating, 36 reviews
Ocean Sounds by Turtle Bay
5.0 out of 5 average rating, 18 reviewsQuick 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!
Destinations to explore
- Waikiki Beach
- Lanikai Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Kapiolani Park Beach
- Honolulu Zoo
- Banzai Pipeline
- Kailua Beach Park
- Polynesian Cultural Center
- Kalama Beach Park
- Kepuhi Beach
- Ko Olina Golf Club
- Wet 'n' Wild Hawaii
- Waimea Valley
- Bishop Museum
- Hanauma Bay Nature Preserve
- Sharks Cove
- Hawaii Convention Center
- Ala Moana Center
- Dole Plantation
- Waimea Bay Beach
- Turtle Bay Golf
- Iolani Palace





