
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.

Waikiki Gem, Stunning Ocean View, Parking Included
Wake up to breathtaking ocean views from our newly renovated 1BR, 1BA condo. Relax on the lanai, let in the gentle breezes, and soak in the picturesque surroundings. With enough space for up to 4 guests, this retreat is perfect for couples, small families, or close friends seeking solace and tranquility. Immerse yourself in the calming ambiance of modern furnishings and a soothing color palette. Convenient parking included. Discover a blissful sanctuary where serenity and relaxation harmonize.

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

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.

26 B FLR- High Flr. Studio w/ Ocean Views
Your dream Vacation to Waikiki, Hawaii is about to begin! Wake up to amazing ocean view from our 26th floor, completely remodeled beautiful studio. Everything is brand new in this cozy comfortable sweet home. Then, after a day of adventuring in the world-famous island O'ahu, come back to a comfortable brand new queen bed, modern kitchen with a big refrigerator and induction cook top, a coffee & tea station to relax and unwind. This is your vacation to enjoy, and we can't wait to host you.

The Turtle Bay Signature
Come enjoy this newly updated, designer inspired, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave this tropical paradise. Everything has been updated, including hand-picked pendants that can be dimmed to suit your mood. There is a nearby pool, beach and tropical walking trails. Restaurants and shops can be found at the newly renovated Turtle Bay hotel.

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.

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 with Great Amenities
Experience Turtle Bay without resort pricing! - 1-bedroom + loft, 2-bath unit - Spacious master bedroom with king bed - Fully equipped kitchen and stylish living room - Access to 3 pools, tennis courts, and BBQ facilities - Beach Gear provided for your beach days - Great location close to North Shore activities, including the PCC and LDS temple. - Near beach - Explore nearby attractions like Shark's Cove and the Polynesian Cultural Center.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

Mauna View by AvantStay | 10min to Beach, Backyard

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

Slice of Paradise-3BR- Sleeps10-Max 8 Adults

Sunny Heaven 1 Bd Plus Loft
Apartment rentals with a pool

Turtle bay retreat

32nd Floor Penthouse. 3min walk to Waikiki Beach

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

Luxe Loft at Turtle Bay

41F-Island Colony Studio-Ocean & City Skyline View

North Shore Getaway - Newly renovated!

$20 Parking! Cute Waikiki studio with Work space

Relaxing amazing Ocean and Diamond Head View
Other holiday rentals with a pool

Top FL-Luxury Ocean View King Suite-Waikiki Beach~

Modern Unit with Stunning Waikiki View w/ Lanai

Panoramic Oceanfront Home - Newly Remodeled

THE GRAND EXPERIENCE

Ilikai collection # 8. Beach Views and great value

37F-Ultra Upscale Ocean View-Modern 1BR W/Parking!

Kuilima Estates West at Turtle Bay with King Bed

Retro Waikiki Studio 21st FLR with View
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $576 SGD | $475 SGD | $543 SGD | $638 SGD | $760 SGD | $779 SGD | $638 SGD | $633 SGD | $507 SGD | $475 SGD | $475 SGD | $481 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 $89 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
- Kailua Beach
- Waimea Bay Beach
- Kualoa Ranch
- Lanikai Beach
- Ala Moana Beach Park
- Banzai Pipeline
- Honolulu Zoo
- Kepuhi Beach
- Kapiolani Park Beach
- Hanauma Bay Nature Preserve
- Kailua Beach Park
- Waimea Valley
- Bishop Museum
- Wet 'n' Wild Hawaii
- Kalama Beach Park
- Dole Plantation
- Pyramid Rock Beach
- Ko Olina Golf Club
- Polynesian Cultural Center
- Sharks Cove
- Iolani Palace
- Waikiki Aquarium
- Turtle Bay Golf
- Things to do Kailua
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- Things to do United States
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