Vacation rentals with a pool in Kailua-Kona

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Top-rated rentals with a pool in Kailua-Kona

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Captain Cook

4.98 out of 5 average rating, 169 reviews

Tiny House Hawaii

The Tiny House is ready to welcome you to a drop of heaven on the Big Island!🌴 Please be my guest for an exquisite experience in beauty, peace, and tranquility! The Tiny House is a separate guest quarters attached to the main house by only a breezeway. It has its own private entrance, covered lanai, and private yard. Everything you need for an amazing stay is included--- all cooking amenities, beach towels and chairs. The main house has a solar heated pool which is available for Tiny House guests, and a large deck with magnificant ocean and sunset views. Contact us at hitinyhouse@gmail.com for more information or to inquire about booking a stay.

Guest favorite

Condo in Kailua-Kona

4.93 out of 5 average rating, 167 reviews

Aloha Paradise! Remodeled with A/C & Ocean View!

Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

Guest favorite

Guest suite in Hōlualoa

4.9 out of 5 average rating, 345 reviews

Monkey Pod Villa- Guest Suite w/ Pool & Patio

Perched on the cool hillside above Kona, escape to this private retreat on a country estate. Located off the beaten path and away from tourist areas but a 7 mile scenic drive to town & pristine beaches. Awaken from a peaceful night’s sleep to a symphony of the island’s delightful birds. Enjoy a cup of coffee on the garden patio under the shade of a majestic monkey pod tree. After a day of Big Island adventures, unwind with a dip in the sparkling pool and savor the breathtaking Hawaiian sunset.

Superhost

Condo in Kailua-Kona

4.84 out of 5 average rating, 543 reviews

Kona Islander Inn #135

Our studio condo is in the heart of Kona town, on Ali'i Drive, right across the street from the ocean. An easy location if you are looking to walk to many of Kona's best restaurants, snorkel at the nearby pier, or join a manta ray night dive and only 15 minutes from the airport. Our place has great ambiance, the outdoor area, pool and hot tub are stunning, surrounded by tiki torches every evening. Our place is good for couples and small families. One queen bed and a queen pull out sofa-bed.

Superhost

Condo in Kailua-Kona

4.79 out of 5 average rating, 120 reviews

Beautiful Kona Condo in the middle of Ali'i Drive.

Walk Everywhere! Kona Farmer's Market, shops, restaurants, ABC stores are all in walking distance. The ocean is across the street. The pool and hot tub are just outside the back door of our condo. You can watch the sun set everynight over the ocean, and have a one minute walk back. The laundry room is right outside of the front door for you. The grills and tables are inside the pool area, again, just outside the back door. This is a very clean, cozy, updated condo!! We hope you love it!

Guest favorite

Condo in Kailua-Kona

4.96 out of 5 average rating, 114 reviews

Downtown Kona Plaza Condo w/AC

Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

Guest favorite

Condo in Kailua-Kona

4.9 out of 5 average rating, 392 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Guest favorite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 111 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

Guest favorite

Condo in Keauhou

4.86 out of 5 average rating, 103 reviews

Hale Kapena (Captain's House)

Hale Kapena (Captain's House) is a cute golf course frontage condo with peekaboo ocean views. This cozy unit features one full bedroom and a convertible second sleeping area in the living room area. Great for visiting guests or children. This ground floor unit offers easy access with a reserved parking place. Hawaii accommodation taxes of 2023 should be be included in quotes. Also early check-in or late check-out, if available, can be requested for additional fees.

Guest favorite

Guest suite in Kailua-Kona

4.96 out of 5 average rating, 110 reviews

Oceanview Bungalow in Kona

Sun-kissed ocean & pool views delight! Cozy, petite, stylish space. This truly is a small bedroom, but a perfect budget friendly, clean, cool, place to sleep. Private bathroom, bamboo linens, refrigerator, microwave, and AC help make this an ideal getaway! . Located near downtown Kailua-Kona and 500 ft above sea level, this fantastic spot offers cooler temperatures and breezes that delight guests. Come enjoy the Big Island’s aloha spirit.

Guest favorite

Rental unit in Kailua-Kona

4.96 out of 5 average rating, 238 reviews

KJ's Place, in the heart of the city.

We would like to welcome you to your "home away from home" on the beautiful Big Island! Relax in this stunning, remodeled Kona Ali'i condominium and experience clean, luxurious accomodations in the heart of the city. From here you are within walking distance of all Kona has to offer; from restaurants and shops, to swimming, the Ironman Village (in Oct) & the Christmas Parade (in Dec). We hope you enjoy your stay!

Superhost

Condo in Kailua-Kona

4.85 out of 5 average rating, 149 reviews

Luxury in the Heart of Kona

We are located in the heart of Kona town. You can walk to yummy restaurants, the farmer's market, 2 beaches, great island shopping and fun island activities. Our condo has been remodeled with tile floors, granite countertops, an added kitchenette, and beautiful all wood furniture. We recently replaced the mattress as well. Our unit overlooks the pool and the beautiful Islander Inn tropical gardens.