
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.

32nd Floor Penthouse. 3min walk to Waikiki Beach
Welcome to HaleHinano Penthouse, Waikiki Beach. Enjoy this rarely find 1BR Penthouse on the 32nd floor with panoramic ocean views of the crisp Hawaiian waters. This condo is fully renovated with modern furnishings and decor. Just a few steps away, you’ll be at beach fronts of Waikiki beach. You’ll be surrounded with local favorite fine dining, shopping plazas. -In unit washer and dryer. -Top roof Pool, Jacuzzi, BBQ -3 min walk to the Waikiki beach. -$35/day parking attached to the building.

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.)

Ocean View w/ 2 private balconies; Steps to Beach
BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!

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.

Oceanfront Paradise (Car & Parking Available)
* Aloha! Welcome to our beachfront home with a unique design! * Enjoy incredible ocean views, a spacious lanai, a full kitchen, and modern amenities. Sip your morning coffee while watching the ocean, sailboats, surfers, or even whales. You can also watch fireworks directly from the lanai every Friday! The condo is right on Waikiki Beach. Just a short walk to the beaches, restaurants, bars, shopping centers, and more. Hawaii is our happy place. I hope it can bring you some happiness too. :-)

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.

NEWLY RENOVATED (2021) Turtle Bay Haven!
NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks
Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

Rated Top 1% 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.

Spectacular Views - Spacious 2BR Waikiki Penthouse
Enjoy this once in a lifetime ocean view in the heart of Waikiki. This spacious 2 bedroom, 2 bathroom penthouse provides all the necessities for the perfect Hawaiian holiday. Located across the street from the world-famous Waikiki Beach, you have easy walking access to restaurants, shops and entertainment. This picturesque penthouse offers new appliances, comfortable beds, in-house laundry, A/C, a lanai with a spectacular view and more. Your dream vacation awaits!
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

Family Oceanview Oasis, Hot Tub, 5min to beach

"Piece of Paradise!" Luxurious 4-bed

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

Kalo Homes - Makaha's Hidden Gem
Apartment rentals with a pool

Million $ View on Gorgeous Secluded Beach!

Renovated Studio Waikīkī Beach Shopping Restaurant

Ko Olina Beach Villas ★Ocean View★Free Parking★

Turtle bay retreat

The Seascape at Turtle Bay

Ko Olina Beach! Largest villa w/2 Masters, Nov 13

Alamoana Hotel 29FL Studio City&Partial Ocean View

Hale Soleil
Other holiday rentals with a pool

Modern Unit with Stunning Waikiki View w/ Lanai

Renovated Boutique-Style Ocean View | Secret Door!

17F-Beautiful & Upscale-Waikiki Beach 1BR/Parking~

( Golden Week ) Nr beach! Imperial Resort

Kuilima Estates West at Turtle Bay with King Bed

Ocean View Studio with private balcony

29FL-Modern & Chic Ocean View 1BR w/Free Parking~

Ocean View Sunset, Free Parking, Pool, 5m to Beach
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £346 | £285 | £326 | £383 | £456 | £467 | £383 | £380 | £304 | £380 | £359 | £391 |
| 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 1,530 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

4.9 Average rating
Kailua stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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