
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.

Secluded White Sandy beach just 30 steps away
Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

Amazing Beachfront Condo!
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.)

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!

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu
Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

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. :-)

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.

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks
Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

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.

Spectacular Views - Spacious 2BR Waikiki Penthouse
Enjoy this once in a lifetime ocean view in the heart of Waikiki. This spacious 2 bedroom, 2 bathroom penthouse provides all the necessities for the perfect Hawaiian holiday. Located across the street from the world-famous Waikiki Beach, you have easy walking access to restaurants, shops and entertainment. This picturesque penthouse offers new appliances, comfortable beds, in-house laundry, A/C, a lanai with a spectacular view and more. Your dream vacation awaits!

♥ North Shore Paradise at Turtle Bay ♥
For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.
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!

Large family home 5 min from beach- with pool

Top 5% Family-Friendly Home By Beach -Honu Hideout

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

Kalo Homes - Makaha's Hidden Gem

Sunny Heaven 1 Bd Plus Loft
Condo rentals with a pool

Ko Olina Beach Villas ★Ocean View★Free Parking★

The Seascape at Turtle Bay

Turtle bay retreat

★Panoramic OCEAN VIEW Studio Suite + FREE Parking

Hale Soleil

North Shore Getaway - Newly renovated!

NEW*STUNNING Luxury 1BR Ocean View*Central Waikiki

Ilikai Newly Renovated Ocean View One Free Parking
Other vacation rentals with a pool

16P - Hawaiian Princess - Plumaria Paradise

MOANA Ocean View Suite • 31st Floor • FREE Parking

New Listing! Ocean & DiamondHead View/Free Parking

( Golden Week ) Nr beach! Imperial Resort

Kuilima Estates West at Turtle Bay with King Bed

37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~

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

Aloha Surf Condo - Private Deck - Pool
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 R1,214 ZAR per night before taxes and fees
Verified guest reviews
Over 1,530 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
90 of Kailua vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua rentals
4.9 Average rating
Kailua stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- O‘ahu Vacation rentals
- Kauaʻi County Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikiki Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kihei Vacation rentals
- Kona Vacation rentals
- Kaanapali Vacation rentals
- Hilo Vacation rentals
- Princeville Vacation rentals
- North Kona Vacation rentals
- Apartment rentals Kailua
- Rentals with a patio Kailua
- Rentals with an EV charger Kailua
- Guesthouse rentals Kailua
- Rentals with outdoor seating Kailua
- Private suite rentals Kailua
- Rentals with a hot tub Kailua
- House rentals Kailua
- Rentals with a washer and dryer Kailua
- Rentals with beach access Kailua
- Pet-friendly rentals Kailua
- Condo rentals Kailua
- Beach condo rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Beachfront rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a kayak Kailua
- Villa rentals Kailua
- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Mālaekahana Beach
- Honolulu Zoo
- Ala Moana Beach Park
- Banzai Pipeline
- Mākoa Beach
- Kalama Beach
- Hanauma Bay
- Kapiolani Park Beach
- White Plains Beach
- Sans Souci Beach
- Bishop Museum
- Kahala Hilton Beach
- Wet 'n' Wild Hawaii
- Nimitz Beach
- Diamond Head Beach Park
- Pyramid Rock Beach
- Ke Iki Beach
- Kalani Beach
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Nature and outdoors Honolulu County
- Wellness Honolulu County
- Entertainment Honolulu County
- Sports activities Honolulu County
- Art and culture Honolulu County
- Things to do Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Art and culture Hawaii
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States