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

"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!

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.

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.)

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. :-)

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.

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.

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.

Luxe Loft at Turtle Bay
Our Luxe Loft is located at Turtle Bay Kuilima Estates East on the North Shore of Oahu. Nestled in between the world famous Palmer Golf course, you will enjoy resort amenities with the comfort of condo living. The North Shore of Oahu is referred to as the 7 mile miracle, for its beautiful white sand beaches, world class waves and crystal blue waters. From Hale'iwa Beach Park to Sunset Beach, you will find the most beautiful shore line found anywhere on earth. It is truly a magical place.

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!

Rated Top 5% 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.

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.

Oceanfront Home (Beautiful Sunset View Every Day)
* Aloha! Welcome to our happy place with amazing sunset every day! * If you are looking for wide open ocean and sunset views directly from your balcony/lanai, this is it! You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Our spacious bedroom, full kitchen, and freshly updated bathroom will make you feel just like home. Welcome to our little paradise!
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Waikiki Gem, Stunning Ocean View, Parking Included

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

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

Large family home 5 min from beach- with pool

Spacious 1 Bedroom Condo in Turtle Bay

Makaha Hale - Serene 3 BR Home

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

Slice of Paradise-3BR- Sleeps10-Max 8 Adults
Condo rentals with a pool

Beach Front Waikīkī Condo- Free Parking

The Seascape at Turtle Bay

Turtle bay retreat

Turtle Bay Condo. Cozy retreat for two.

North Shore Getaway - Newly renovated!

Newly Renovated | Low-Toxic Waikiki Airbnb

Ocean View w/ 2 private balconies; Steps to Beach

*Serendipity on the Moana! - Legal & Beachfront!*
Other vacation rentals with a pool

Beautiful OceanView&Sunset @IlikaiResort w/Parking

New Listing! Stylish Waikiki Condo - Free Parking

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

Kuilima Estates West at Turtle Bay with King Bed

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

32FL-Upscale Luxury Penthouse Ocean View Studio~

Sunset Hale

*The Maeva* Upscale with Views and Free Parking
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,671 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,576 | ﺩ.ﺇ1,851 | ﺩ.ﺇ2,204 | ﺩ.ﺇ2,259 | ﺩ.ﺇ1,851 | ﺩ.ﺇ1,836 | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,836 | ﺩ.ﺇ1,737 | ﺩ.ﺇ1,888 |
| Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Quick stats about vacation rentals with a pool in Kailua

Total vacation rentals
Explore 90 vacation rentals in Kailua

Nightly prices starting at
Kailua vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,540 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Kailua vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua rentals

4.8 Average rating
Kailua stays are highly rated by guests—averaging 4.8 out of 5!
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- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Lanikai Beach
- Ala Moana Beach Park
- Kepuhi Beach
- Banzai Pipeline
- Honolulu Zoo
- Kapiolani Park Beach
- Mākua Beach
- Bishop Museum
- Waimea Valley
- Wet 'n' Wild Hawaii
- Kailua Beach Park
- Waimea Bay Beach
- Pyramid Rock Beach
- Kalama Beach Park
- Dole Plantation
- Iolani Palace
- Waikiki Aquarium
- Ko Olina Golf Club
- Makapuʻu Beach
- Turtle Bay Golf
- Mākaha Beach Park
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