
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.)

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

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.

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!

Rated Top 5% Airbnb: Privacy & Luxury @ Turtle Bay
Relax in complete privacy at your newly renovated end-unit retreat, nestled among tropical greenery and filled with high-end touches. From the spa-style bathroom to the gourmet kitchen, every detail is designed for your comfort and care. Sip fresh espresso surrounded by original art from noted local artists, South Pacific antiques, and the cool air of a powerful split A/C. Modeled after 5-star Hawaiian resort bungalows, this peaceful hideaway invites you to unwind in quiet luxury.

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.

Studio at Marriott vacation club ko olina
Feel free to message me a request to book and the times you are looking for. The price shown is for the Mountain View Studio w/kitchenette that sleeps 4, 1 King and a Sofa Bed. Price is over half of the cost if you book direct with the hotel. Also includes FREE parking where hotel charges $45/day. The most beautiful resort and Guest room in Ko Olina right on the beach in a picturesque lagoon. 30 minutes from the airport and Honolulu. * Free WiFi, Free self-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.

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.

Turtle Bay Condo. Amazing retreat!
* North Shore * Pristine beaches * Rocky shores * Beautiful mountains * 2 PGA golf courses * Horseback riding * Surfing/kayaking/paddle board * Hiking/biking trails * Activity rentals * Restaurants/bars * Entire condo * Comfortable living space * Outdoor amenities * Gated entry * Assigned parking * On-site security guard * Three swimming pools * 2 tennis courts * 4 Pickle ball courts Suitable for couples, adventurers, business travelers, and families.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Waikiki Gem, Stunning Ocean View, Parking Included

Haku Hideout ~ Top 5% Home on Airbnb!

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Family Ocean Oasis, Hot Tub, 5 min drive to beach

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

Oahu Perfect Vacation #1 Family Home, Pool Hot Tub

Luxe Turtle Bay - 3 En-Suite, A/C, golf course
Apartment rentals with a pool

Spacious 1BR Ocean/Sunset View w/Parking

The Seascape at Turtle Bay

Modern & clean condo at Turtle Bay

Hale Koa (Newly updated condo with split AC)

Nalu Blue - Turtle Bay

Luxe Loft at Turtle Bay

North Shore Getaway - Newly renovated!

Elegant, Spacious Downtown Hideaway w/Parking
Other holiday rentals with a pool

NEW! Aloha OceanView Haven @IlikaiResort w/Parking

Villa 302, King bed, Penthouse Lvl Ocean View Turt

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Breathtaking Ocean View Luxury Villa

Opihi NEW waikiki 1B+fun bunk washer parking!

3-Minute Walk to Beach, Free Parking/Pool/Wi-Fi

Hale Moana by AvantStay | Incredible Beach Resort

Kuilima Estates West at Turtle Bay with King Bed
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £345 | £285 | £326 | £383 | £456 | £467 | £383 | £380 | £304 | £285 | £285 | £289 |
| 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 £53 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
- Kailua Beach
- Lanikai Beach
- Waimea Bay Beach
- Kualoa Ranch
- Ala Moana Beach Park
- Honolulu Zoo
- Banzai Pipeline
- Kapiolani Park Beach
- Kepuhi Beach
- Hanauma Bay Nature Preserve
- Bishop Museum
- Kailua Beach Park
- Waimea Valley
- Wet 'n' Wild Hawaii
- Kalama Beach Park
- Polynesian Cultural Center
- Sharks Cove
- Ko Olina Golf Club
- Dole Plantation
- Pyramid Rock Beach
- Turtle Bay Golf
- Waimea Bay Beach
- Waikiki Aquarium
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