
Vacation rentals with a pool in Kailua
Find and book unique homes with a pool on Airbnb
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 ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,670 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

4.8 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.

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ
Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!

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

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.

"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 & FREE parking!

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.

The Kulima Beach Loft
Plan a couples romantic getaway, remote work trip or family retreat! Wake up to the birds chirping and the tropical breezes blowing through the trees in this bright newly renovated condo at Turtle Bay. Located on Oahu's famous north shore - minutes from the beach, restaurants, shops at Turtle Bay Resort and a short drive to snorkeling and surf at Sunset Beach. Fully stocked with local goodies. Local owners means all the insider tips for a great trip.

♥ 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

Ocean View Home for Family Fun Getaway Near Beach

Waikiki Gem, Stunning Ocean View, Parking Included

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Sleep 12, Hot Tub, Beach 5 min | Oahu West Side

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

Kaia Villa at Turtle Bay/North Shore Oahu

Sunny Heaven 1 BD + Loft
Condo rentals with a pool

Spacious 1BR Ocean/Sunset View w/Parking

Lovely Stay in Turtle Bay

Turtle bay retreat

RusticLuxe — Go Fully Custom at Turtle Bay

2BR High Floor Free Parking

Hale Koa (Newly updated condo with split AC)

Cozy Ocean View Retreat Steps from Waikiki Beach

Secluded White Sandy beach just 30 steps away
Other vacation rentals with a pool

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Ocean Front Luxurious Villa

Hidden gem at North Shore Turtle Bay

Villa 317 King bd Penthouse Ocean View TurtleBay

Kuilima Estates West at Turtle Bay with King Bed

Hawaiian sunrise retreat

Beautiful Newly Renovated North Shore Condo !

Aloha Surf Condo - Private Deck - Pool - E-Bikes
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,671 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,576 | ﺩ.ﺇ1,851 | ﺩ.ﺇ2,204 | ﺩ.ﺇ2,259 | ﺩ.ﺇ1,851 | ﺩ.ﺇ1,836 | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,396 |
| 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 |
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- Waikiki Beach
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- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Honolulu Zoo
- Banzai Pipeline
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- Bishop Museum
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- Wet 'n' Wild Hawaii
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- Kalama Beach Park
- Ko Olina Golf Club
- Sharks Cove
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