
Holiday rentals with a pool in Kailua
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Kailua

Total holiday rentals
Explore 80 holiday rentals in Kailua

Nightly prices starting at
Kailua holiday rentals start at $101 AUD per night before taxes and fees

Verified guest reviews
Over 1,430 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!
Top-rated rentals with a pool in Kailua
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Honu Hideout at Turtle Bay
Come escape to Honu Hideout on the exclusive North Shore of Oahu, and enjoy this newly renovated ground floor unit situated just a short walk away from the iconic Turtle Bay Resort and the most breathtaking and secluded beaches on Oahu. Far away from the hustle and bustle of Honolulu, this unit offers the peacefulness of the country and the proximity to infamous attractions for the vacation of your dreams. Relax and restore or adventure and explore, you choose, all within minutes of your door.

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.

Makaha Hale - Serene 3 BR Home
Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

Turtle Bay Corner Condo With A Fairway View!
Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th w/cool breezes, new washer & dryer, and A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax there and enjoy a true authentic Hawaiian experience!

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.

NEWLY RENOVATED (2021) Turtle Bay Haven!
NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

Best Kept Secret on Oahu! and WE ARE LICENSED!!!
Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

Cottage Nene - Luxury Home by Beaches & Mountains
Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym
Escape to paradise in this brand new vacation rental located in the secluded Makaha Valley. Just a short drive away from some of the world's most beautiful beaches, enjoy endless opportunities for hiking, golfing, and soaking up the sun. Surrounded by lush mountains and pristine nature, this rental offers the perfect retreat from the hustle and bustle of everyday life. Take in the breathtaking ocean and mountain views and create unforgettable memories in this ultimate tropical getaway.

SEArider TWO at Turtle Bay
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, This unit has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. This unit sits directly below our other property, SEArider ONE(search on airbnb).

"Coconut Cottage by the Sea" Steps to the beach!
Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym & security.

♥ 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

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2

Hawaii Kai 7-Bedroom Pool Home with Views!

Newly Renovated Villa Walk to Beach + Pool

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!
Condo rentals with a pool

The Seascape at Turtle Bay

Turtle Bay Condo. Cozy retreat for two.

Secluded White Sandy beach just 30 steps away

North Shore Getaway - Newly renovated!

Surfer’s North Shore, Turtle Bay - Legal Rental

Amazing Waikiki Beach Views!!

Walk to beach, pool, tennis, golf, restaurants, AC

Turtle Bay Condo Linoe
Other holiday rentals with a pool

NEW! Aloha OceanView Haven @IlikaiResort w/Parking

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Turtle Bay Designer Renovated Walk to Beach • Pool

Ilikai Penthouse-Luxury Oceanview 2BR/2BTH/Parking

Beautiful Newly Renovated North Shore Condo !

Aloha Surf Condo - Private Deck - Pool - E-Bikes

Sunset Hale

33F-Financial District-Harbor View-1BR w/Parking
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $723 AUD | $542 AUD | $506 AUD | $728 AUD | $867 AUD | $889 AUD | $728 AUD | $723 AUD | $578 AUD | $542 AUD | $542 AUD | $549 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 |
Destinations to explore
- Luxury rentals Kailua
- Guesthouse rentals Kailua
- House rentals Kailua
- Villa rentals Kailua
- Rentals with a washing machine and dryer Kailua
- Beach condo rentals Kailua
- Rentals with a kayak Kailua
- Pet-friendly rentals Kailua
- Rentals with a hot tub Kailua
- Beachfront rentals Kailua
- Private suite rentals Kailua
- Rentals with a patio Kailua
- Family-friendly rentals Kailua
- Rentals with an EV charger Kailua
- Apartment rentals Kailua
- Rentals with outdoor seating Kailua
- Rentals with beach access Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Condo rentals Kailua
- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Waikiki Beach
- Kailua Beach
- Lanikai Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Honolulu Zoo
- Kapiolani Park Beach
- Banzai Pipeline
- Kailua Beach Park
- Polynesian Cultural Center
- Bishop Museum
- Kepuhi Beach
- Hanauma Bay Nature Preserve
- Wet 'n' Wild Hawaii
- Waimea Valley
- Ko Olina Golf Club
- Kalama Beach Park
- Hawaii Convention Center
- Ala Moana Center
- Sharks Cove
- Dole Plantation
- Turtle Bay Golf
- Waimea Bay Beach
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Wellness Honolulu County
- Entertainment Honolulu County
- Sightseeing Honolulu County
- Art and culture Honolulu County
- Nature and outdoors Honolulu County
- Things to do Hawaii
- Tours Hawaii
- Nature and outdoors Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Food and drink Hawaii
- Art and culture Hawaii
- Entertainment Hawaii
- Things to do United States
- Sightseeing United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Art and culture United States
- Sports activities United States
- Wellness United States
- Nature and outdoors United States







