
Vacation 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.

Golf Course Serenity at Turtle Bay
Great Location! Golf Course front. Newly remodeled, single level ground floor condo, with beautiful views. Free parking and Wifi. Walking distance to Turtle Bay Resort, Beaches, Tidal Pools, and Restaurants. This Kuilima Estates West 1 bedroom unit, is fully equipped with King size bed in master bedroom and queen size sofa sleeper in living room. Flat screen TV in Living and bedroom. Lanai opens out to a garden area. Family-friendly activities. great for couples, adventurers, business traveler

Secluded White Sandy beach just 30 steps away
Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

"Endless Summer" Beachfront Condo w/ Full Kitchen!
Welcome to the beach! Your little piece of paradise! This 1 large bedroom has a new king bed, and there is a bed in the living room as well. Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped remodeled kitchen, washer/dryer & private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

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!

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. :-)

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!

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.

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

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.

♥ 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

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 - Near Beach, Ocean views, Gym, & Pool
Condo rentals with a pool

RusticLuxe — Go Fully Custom at Turtle Bay

Hale Soleil

The Coloradoan

NEW*STUNNING Luxury 1BR Ocean View*Central Waikiki

Rated Top 1% Airbnb: Privacy & Luxury @ Turtle Bay

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

*Serendipity on the Moana! - Legal & Beachfront!*

NEWLY RENOVATED (2021) Turtle Bay Haven!
Other vacation rentals with a pool

Penthouse Upscale Oceanview King Studio Near Beach

MOANA Suite • Panoramic Ocean View • FREE Parking

33FL-DiamondHD & Ocean View-Upscale-1BR w/Parking

New Listing! Ocean & DiamondHead View/Free Parking

Lux Panoramic Beach Views - Free Parking!

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

37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~

34FL-Upscale Mountain View 1BR-Waikiki w/Parking
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.ﺇ1,836 | ﺩ.ﺇ1,737 | ﺩ.ﺇ1,888 |
| 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 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 1,530 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

4.9 Average rating
Kailua stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- Oahu Vacation rentals
- Kauaʻi County Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikiki Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kona Vacation rentals
- Kihei Vacation rentals
- Kaanapali Vacation rentals
- North Kona Vacation rentals
- Princeville Vacation rentals
- Hilo Vacation rentals
- Guesthouse rentals Kailua
- Villa rentals Kailua
- House rentals Kailua
- Rentals with a washer and dryer Kailua
- Beach condo rentals Kailua
- Rentals with a kayak Kailua
- Rentals with a hot tub Kailua
- Pet-friendly rentals Kailua
- Rentals with a patio Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Family-friendly rentals Kailua
- Rentals with beach access Kailua
- Rentals with outdoor seating Kailua
- Condo rentals Kailua
- Private suite rentals Kailua
- Apartment rentals Kailua
- Beachfront rentals Kailua
- Rentals with an EV charger Kailua
- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Lanikai Beach
- Kepuhi Beach
- Ala Moana Beach Park
- Mālaekahana Beach
- Honolulu Zoo
- Banzai Pipeline
- Kapiolani Park Beach
- Kalama Beach
- Mākoa Beach
- Hanauma Bay
- White Plains Beach
- Sans Souci Beach
- Bishop Museum
- Kahala Hilton Beach
- Waimea Bay Beach
- Diamond Head Beach Park
- Nimitz Beach
- Wet 'n' Wild Hawaii
- Ke Iki Beach
- Kalani Beach
- Makao Beach
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Tours Honolulu County
- Wellness Honolulu County
- Entertainment Honolulu County
- Art and culture Honolulu County
- Nature and outdoors Honolulu County
- Sightseeing Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Food and drink Hawaii
- Wellness Hawaii
- Entertainment Hawaii
- Art and culture Hawaii
- Things to do United States
- Sightseeing United States
- Tours United States
- Wellness United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States






