
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 $119 NZD 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.

Dreamy Beachfront Home (Car & Parking Available)
* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls and more. Every time I come to Hawaii, I am happy. I hope our place can bring you happiness too. :-)

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

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.

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen
Whether you are planning a perfect romantic getaway or a much deserved quality family time vacay for FOUR, this high floor apartment w/ocean views checks all the boxes. The 1 bedroom with the KING BED is ideal for the parents, while the kids share the QUEEN SLEEPER SOFA in the living room. The kitchen is fully stocked w/everything you will need to prepare meals, drinks and snacks. It's a 4 minute walk to the beach. There is 1 FREE PARKING spot and there's NO RESORT FEES. Close to shops & food.

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!

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.

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 ONE at Turtle Bay
~ You just found your Base Camp to explore the North Shore of Oahu ~ Our condo has just been completely remodeled and redecorated with two brand new bathrooms. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the ocean. Enjoy the resort amenities of Turtle Bay coupled with the comfort of condo living. Health and comfort are top priority. We pride ourselves on a clean home and have implemented additional measures for sanitization.

♥ 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!

4 Bedroom Luxury Home in Makaha Valley

He'e Hideout ~ Airbnb’s Top 1% Most Desired Home

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!
Condo rentals with a pool

"Coconut Cottage by the Sea" Steps to the beach!

The Seascape at Turtle Bay

Luxury Condo with Ocean Views & FREE Parking!

Ranked Top 1% Airbnb-Privacy & Luxury @ Turtle Bay

Elegant, Spacious Downtown Hideaway w/Parking

North Shore Oahu Getaway at Turtle Bay Resort

#3103 2BR/2BA|Beachfront, Free Parking, Gym & Pool

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

Aloha OceanView Haven @IlikaiResort w/Parking

Turtle Bay Hale: Renovated 2025, Golf Course Front

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Modern Unit with Stunning Waikiki View w/ Lanai

(Golden Week) Nr beach! Imperial Resort

32F-Penthouse Pacific Monarch Studio-Ocean View

Sunset Hale

Aloha Surf Condo - Turtle Bay - AC + 2 E-Bikes
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $851 NZD | $638 NZD | $596 NZD | $623 NZD | $623 NZD | $638 NZD | $858 NZD | $851 NZD | $681 NZD | $638 NZD | $638 NZD | $647 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 |
Destinations to explore
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- Rentals with pools Honolulu County
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- Waikiki Beach
- Kailua Beach
- Lanikai Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Kapiolani Park Beach
- Honolulu Zoo
- Banzai Pipeline
- Kailua Beach Park
- Polynesian Cultural Center
- Bishop Museum
- Wet 'n' Wild Hawaii
- Hanauma Bay Nature Preserve
- Kepuhi Beach
- Waimea Valley
- Ko Olina Golf Club
- Kalama Beach Park
- Sharks Cove
- Hawaii Convention Center
- Dole Plantation
- Ala Moana Center
- Turtle Bay Golf
- Waimea Bay Beach
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
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- Nature and outdoors Honolulu County
- Art and culture Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
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- Things to do United States
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