
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.

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.

Absolutely Oceanfront-60'Waterfall Pool-Legal
Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

North Shore Turtle Bay Renovated 2Bd/2Ba + Loft
Aloha and welcome to our spacious and beautifully renovated North Shore Turtle Bay Resort 2 Bedroom condo that includes an additional 3rd loft room + 2 bathrooms. Directly outside the living room is a large manicured grassy lawn and the Fazio Golf Course. This gated condo is a short walk to the 5 Star Ritz Carlton Turtle Bay and all of its amenities, Lei Lei's Bar & Grill, Roy's Beach House, and a beautiful white sandy beach. Swimming pool and tennis courts on site! Welcome home to paradise!

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

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym
Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We've got you covered with all the beach amenities you'll need to enjoy the crystal-clear waters and white sandy beaches. Whether you're looking for a romantic escape or a fun-filled family vacation, our property has everything you need to create unforgettable memories.

Bright stay near Turtle Bay w/ pool & BBQ grill
Welcome to your North Shore escape - a relaxed stay near Turtle Bay w/ easy beach access & resort-style perks. Settle in, unwind, & enjoy island living at your own pace: - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Shared outdoor pool (year-round), tennis & pickleball courts - Beach access + beach essentials & kayak - Private patio or balcony + BBQ grill - Kitchen, Wifi, workspace & in-unit washer/dryer - Family-friendly w/ Pack ’n play/Travel crib & toys

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.

♥ 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

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

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

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

Sunny Heaven 1 Bd Plus Loft

Oahu Perfect Vacation #1 Family Home, Pool Hot Tub
Apartment rentals with a pool

Amazing Ocean & Beach Views - Only Steps to Beach!

Spacious 1BR Ocean/Sunset View w/Parking

32nd Floor Penthouse. 3min walk to Waikiki Beach

2BR High Floor Free Parking

Modern & clean condo at Turtle Bay

Luxe Loft at Turtle Bay

North Shore Getaway - Newly renovated!

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

NEW! Aloha OceanView Haven @IlikaiResort w/Parking

Villa 302, King bed, Penthouse Lvl Ocean View Turt

Modern Unit with Stunning Waikiki View w/ Lanai

Ocean Front Luxurious Villa

Kuilima Estates West at Turtle Bay with King Bed

Beautiful Newly Renovated North Shore Condo !

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

Elegant Luxury OceanView&Fireworks@IlikaiResort+Park
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $585 SGD | $482 SGD | $551 SGD | $648 SGD | $771 SGD | $790 SGD | $648 SGD | $643 SGD | $514 SGD | $482 SGD | $482 SGD | $488 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 |
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 1,540 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
80 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!
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- Waikiki Beach
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- Kualoa Ranch
- Ala Moana Beach Park
- Honolulu Zoo
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