
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 90 holiday rentals in Kailua

Nightly prices starting at
Kailua holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Kailua holiday rentals include wifi 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.

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.)

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.

Ocean View Sunset, Free Parking, Pool, 5m to Beach
Aloha and welcome to one of the most amazing complete remodels you will find in Waikiki - completed end of 2022. This one-of-a-kind 1 bedroom with free 1 parking stall, pool and gym boasts spectacular ocean & Diamond Head views and is only 0.2 miles (5 min walk) from Waikiki Beach and closer to endless restaurants, shopping & so much more. We would love to have you stay with us and create memories in this truly magical place that is centrally-located, well appointed, and with fabulous views!

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!

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.

North Shore Oahu Getaway at Turtle Bay Resort
880 acres of Turtle Bay Resort while staying in our luxury condo. Our beach cottage is a perfect place to relax and unwind. Located at Kuilima Estates West in the Gold Coast "quiet corner" of the property, less car traffic. It's called the Gold Coast for a reason! Enjoy stunning views of the golf course and a peek a boo view of the ocean right from the windows of your living room. Our condo has 3 on site pools, charcoal BBQ pit, tennis courts, and basketball courts in this gated community

3BR, Near Beach, Game RM, Private Spa, Pool, Gym
Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

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.

32F-Penthouse Pacific Monarch Studio-Ocean View
Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.

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

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

Newly Renovated Villa Walk to Beach + Pool

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

Ocean-Sunset Views Home in Gated Makaha Community
Apartment rentals with a pool

Lovely Stay in Turtle Bay

The Seascape at Turtle Bay

RusticLuxe — Go Fully Custom at Turtle Bay

2BR High Floor Free Parking

Modern & clean condo at Turtle Bay

Turtle Bay Condo. Delight in Paradise

Secluded White Sandy beach just 30 steps away

*Serendipity on the Moana! - Legal & Beachfront!*
Other holiday rentals with a pool

NEW! Aloha OceanView Haven @IlikaiResort w/Parking

Beach Front HawaiianPrincessCorner Unit

Cozy Hauula Studio Getaway!

Hidden gem at North Shore Turtle Bay

Hawaiian sunrise retreat

Beautiful Newly Renovated North Shore Condo !

Ocean Sounds by Turtle Bay

Villa 202, KING bed, Amazing Ocean Views, Turtle B
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $640 SGD | $480 SGD | $448 SGD | $645 SGD | $768 SGD | $787 SGD | $645 SGD | $640 SGD | $512 SGD | $480 SGD | $480 SGD | $486 SGD |
| 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
- Family-friendly rentals Kailua
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- Rentals with pools Honolulu County
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- Hilton Hawaiian Village Lagoon
- Waikiki Beach
- Kailua Beach
- Lanikai Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Honolulu Zoo
- Banzai Pipeline
- Kapiolani Park Beach
- Kailua Beach Park
- Kepuhi Beach
- Hanauma Bay Nature Preserve
- Bishop Museum
- Wet 'n' Wild Hawaii
- Waimea Valley
- Polynesian Cultural Center
- Ko Olina Golf Club
- Kalama Beach Park
- Dole Plantation
- Sharks Cove
- Hawaii Convention Center
- Waimea Bay Beach
- Turtle Bay Golf
- Things to do Kailua
- Things to do Honolulu County
- Nature and outdoors Honolulu County
- Food and drink Honolulu County
- Sightseeing Honolulu County
- Wellness Honolulu County
- Art and culture Honolulu County
- Entertainment Honolulu County
- Sports activities Honolulu County
- Things to do Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Art and culture Hawaii
- Entertainment Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Tours Hawaii
- Things to do United States
- Sightseeing United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Wellness United States







