
Holiday 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.

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.

Panoramic Views - Large Modern Suite, Free Parking
Aloha! Enjoy this newly renovated, modern condo just steps away from World Famous Waikiki Beach with panoramic view of Diamond Head and Ocean views on the 36 floor of Waikiki Banyan. The condo is a true, large one-bedroom, with a King size bed in the bedroom, a queen sofa bed in the living room, and a Full kitchen. It is also family friendly, equipped with a crib, high chair and kids' dinnerware. The building has a FREE secured covered parking, sunny pool deck with two hot tubs and fast Wi-Fi.

Absolutely Oceanfront-60'Waterfall Pool-Legal
Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

42FL-Beautiful High-FL Studio w/Ocean & City Views
A stunning island retreat that is sure to take your breath away! This newly renovated king studio is located on the 42nd floor in the heart of central Waikiki. Boasting partial ocean views and an unparalleled vista of the entire Waikiki skyline. This is truly a one-of-a-kind experience that is perfect for couples celebrating a special occasion or small groups looking to make unforgettable memories. With all the necessary amenities, you will feel right at home in this beautiful island paradise.

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.

The Turtle Bay Signature
Come enjoy this newly updated, designer inspired, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave this tropical paradise. Everything has been updated, including hand-picked pendants that can be dimmed to suit your mood. There is a nearby pool, beach and tropical walking trails. Restaurants and shops can be found at the newly renovated Turtle Bay hotel.

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.
Waikiki Studio Free Parking!
Cozy studio with amazing view! FREE PARKING on premises- covered assigned stall, Unlimited In and out access. Convenient location in Waikiki. Walk to Waikiki beach, Restaurants & Ala Moana Shopping Center Secure building with 24 hr security/ building staff Kitchenette with small stove, mini fridge, and microwave Access to Amenity Floor on the 5F: *Laundry facility (Fee $1.50 credit card) 7am-10:50pm *Pool 9am-9pm Must have Review on Airbnb to book Tax and all fee included

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.

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 Kailua rentals with a pool
House rentals with a pool

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

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha

Slice of Paradise-3BR- Sleeps10-Max 8 Adults

Sunny Heaven 1 Bd Plus Loft
Condo rentals with a pool

Minutes to Beach | Pool+Gym | WFH Station | Lanai

10*Waikiki Ocean Park View Condo Parking Available

Nalu Blue - Turtle Bay

Condo with Canal View in Center Waikiki Near Beach

Luxe Loft at Turtle Bay

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

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

Relaxing amazing Ocean and Diamond Head View
Other holiday rentals with a pool

Top FL-Luxury Ocean View King Suite-Waikiki Beach~

Penthouse Upscale Oceanview King Studio Near Beach

Modern Unit with Stunning Waikiki View w/ Lanai

25FL-Upscale Ultra Modern-Premium 1BR W/Parking

Dreamy Beachfront Home (Car & Parking Available)

37F-Ultra Upscale Ocean View-Modern 1BR W/Parking!

Turtle Bay 1 bed with Lanai Renovated Corner Unit

Sunset Hale
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $641 AUD | $528 AUD | $604 AUD | $710 AUD | $845 AUD | $866 AUD | $710 AUD | $704 AUD | $563 AUD | $528 AUD | $528 AUD | $535 AUD |
| 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 holiday rentals with a pool in Kailua

Total holiday rentals
Explore 90 holiday rentals in Kailua

Nightly prices starting at
Kailua holiday rentals start at $99 AUD per night before taxes and fees

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

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Kailua holiday 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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- Waikiki Beach
- Kailua Beach
- Waimea Bay Beach
- Lanikai Beach
- Kualoa Ranch
- Ala Moana Beach Park
- Banzai Pipeline
- Honolulu Zoo
- Kepuhi Beach
- Kapiolani Park Beach
- Hanauma Bay Nature Preserve
- Kailua Beach Park
- Waimea Valley
- Bishop Museum
- Wet 'n' Wild Hawaii
- Kalama Beach Park
- Dole Plantation
- Polynesian Cultural Center
- Ko Olina Golf Club
- Pyramid Rock Beach
- Sharks Cove
- Waikiki Aquarium
- Iolani Palace
- Turtle Bay Golf
- Things to do Kailua
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- Nature and outdoors Hawaii
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- Things to do United States
- Entertainment United States
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