
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.

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.

Waikiki Beachfront Home with Ocean and Beach View
* Aloha! Welcome to our happy place in the heart of Waikiki! * If you are looking for stunning ocean views directly from your bed, 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!

Studio- Ocean View Hideaway
Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Waikiki Gem, Stunning Ocean View, Parking Included

Haku Hideout ~ Top 5% Home on Airbnb!

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

Family Oceanview Oasis, Hot Tub, 5min to beach

"Piece of Paradise!" Luxurious 4-bed

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10
Condo rentals with a pool

Turtle bay retreat

Hawaiian Happiness on a Budget!

Rated Top 5% Airbnb: Privacy & Luxury @ Turtle Bay

♥ North Shore Paradise at Turtle Bay ♥

Beautiful Oceanfront Paradise Condo

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

North Shore Oahu Getaway at Turtle Bay Resort

NEWLY RENOVATED (2021) Turtle Bay Haven!
Other holiday rentals with a pool

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Kailua Ohana Cottage close to beach

Modern Unit with Stunning Waikiki View w/ Lanai

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

Oceanfront Dream Home (Car & Parking Available)

34FL-Upscale Mountain View 1BR-Waikiki w/Parking

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 | $811 NZD | $668 NZD | $764 NZD | $898 NZD | $1,069 NZD | $1,096 NZD | $898 NZD | $891 NZD | $713 NZD | $891 NZD | $843 NZD | $916 NZD |
| 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 $125 NZD per night before taxes and fees

Verified guest reviews
Over 1,530 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
90 of Kailua holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 Holiday rentals
- Oahu Holiday rentals
- Kauaʻi County Holiday rentals
- Island of Hawai'i Holiday rentals
- Waikiki Beach Holiday rentals
- Kailua-Kona Holiday rentals
- Kona Holiday rentals
- Kihei Holiday rentals
- Kaanapali Holiday rentals
- North Kona Holiday rentals
- Princeville Holiday rentals
- Hilo Holiday rentals
- Beach condo rentals Kailua
- Pet-friendly rentals Kailua
- Villa rentals Kailua
- Guesthouse rentals Kailua
- Rentals with a hot tub Kailua
- House rentals Kailua
- Apartment rentals Kailua
- Private suite rentals Kailua
- Rentals with beach access Kailua
- Beachfront rentals Kailua
- Condo rentals Kailua
- Rentals with outdoor seating Kailua
- Rentals with a washing machine and dryer Kailua
- Rentals with a kayak Kailua
- Family-friendly rentals Kailua
- Rentals with a patio Kailua
- Rentals with an EV charger Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Kailua Beach
- Waimea Bay Beach
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Ala Moana Beach Park
- Mālaekahana Beach
- Honolulu Zoo
- Banzai Pipeline
- Kapiolani Park Beach
- Mākoa Beach
- Kalama Beach
- Hanauma Bay
- White Plains Beach
- Sans Souci Beach
- Bishop Museum
- Waimea Bay Beach
- Kahala Hilton Beach
- Diamond Head Beach Park
- Wet 'n' Wild Hawaii
- Ke Iki Beach
- Nimitz Beach
- Kalani Beach
- Waimea Valley
- Things to do Kailua
- Things to do Honolulu County
- Sports activities Honolulu County
- Art and culture Honolulu County
- Sightseeing Honolulu County
- Nature and outdoors Honolulu County
- Entertainment Honolulu County
- Food and drink Honolulu County
- Tours Honolulu County
- Wellness Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Food and drink Hawaii
- Art and culture Hawaii
- Wellness Hawaii
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Nature and outdoors United States
- Sports activities United States






