Vacation rentals with a pool in Kailua-Kona

Find and book unique homes with a pool on Airbnb

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, 164 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.

Jan 30 – Feb 6

G$37,105 GYD per night

Guest favorite

Guest suite in Kailua-Kona

4.94 out of 5 average rating, 118 reviews

Hale Hapu'u Island Getaway

Welcome to beautiful Kona. Our home is surrounded by beautiful Hapu'u ferns and natural Hawaiian fauna. Relax in the heated salt water pool, take in the beautiful sunsets, or catch up on sleep in your comfortable king sized bed. The perfect location, ten min from the airport, ten min to downtown Kona, and ten to twenty min from half a dozen beautiful beaches. State of Hawaii requires to collect a 17.25% tax on your room. After booking, we will send you a separate Airbnb request for this tax.

Sep 7 – 14

G$26,405 GYD per night

Superhost

Condo in Kailua-Kona

4.89 out of 5 average rating, 124 reviews

Incredible Downtown Kona /Renovated/New Dual AC

Enjoy this wonderful getaway condo located in the heart of Kailua-Kona. Just steps from Alii Drive, the ocean, Kailua-Kona Pier, grocery stores, farmers markets, restaurants, and coffee stores. Fully renovated. Brand new dual AC (in both living and bedroom). In-unit washer/dryer. High speed wifi. One assigned parking space. Beach gears (snorkeling gears, beach chairs, boogie boards, and beach towels) are ready for you to use. And enjoy the saltwater pool that comes with a grill/picnic deck.

Sep 24 – Oct 1

G$33,478 GYD per night

Guest favorite

Guest suite in Hōlualoa

4.9 out of 5 average rating, 335 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.

Aug 10 – 17

G$32,050 GYD per night

Superhost

Condo in Kailua-Kona

4.84 out of 5 average rating, 538 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.

Mar 13 – 20

G$38,492 GYD per night

Superhost

Condo in Kailua-Kona

4.8 out of 5 average rating, 282 reviews

Comfy, Clean & stylish condo w/ ocean&sunset views

Aloha! And welcome to our beautiful condo apartment. It is very comfortable, clean and in the perfect location in Kona. Only two blocks from the ocean and Kailua-Kona town. In 5 minutes you can access plenty of restaurants with a wide variety of food options. Also close by you have the Kona Brewing Company, Cafes and Bars with live music, boutiques, and grocery stores. Whether you like to go for a morning walk on the ocean side with a coffee or out for a romantic dinner this is the spot!

Nov 27 – Dec 4

G$32,092 GYD per night

Guest favorite

Condo in Kailua-Kona

4.97 out of 5 average rating, 197 reviews

Inna's Downtown-Walk to Beach and to Supermarket!

This luxurious condo has just finished a total remodel with custom interior design. It is located in historic downtown Kona from where you can walk to sandy Kailua Bay beach just 2 blocks away, restaurants, supermarket, shopping and entertainment. The condo features: pool with BBQ deck, private laundry, full kitchen with dishwasher and ice maker, two zoned ultra quiet AC, Cal.King bed, a screened in Lanai with peekaboo view of the ocean, fiber optic internet, and a 65” 4K smart TV!

Jul 8 – 15

G$42,425 GYD per night

Superhost

Condo in Kailua-Kona

4.89 out of 5 average rating, 385 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.

Oct 29 – Nov 5

G$34,826 GYD per night

Superhost

Condo in Kailua-Kona

4.9 out of 5 average rating, 147 reviews

Walk around KonaTown Restaurants Beach!

Aloha and E Komo Mai! (Welcome) to Kona Escape! This Hawaiiana inspired 1/bed, 1/bath studio condo with convenience kitchen is beautifully decorated, clean and located on Ali'i Drive in the Village. It is across the street from Kailua Bay and walking distance to restaurants, shops, churches, Kailua Pier, night life, beaches and ocean activities. There is also a large Farmers Market nearby. We are across the street from IronMan Swim Start/Finish line.

Sep 7 – 14

G$30,429 GYD per night

Guest favorite

Condo in Kailua-Kona

4.88 out of 5 average rating, 191 reviews

Kona Hideaway > Pool > Ocean View > AC > Fast Wifi

Hawaii is about views - and this space offers lucky eyes the vast Pacific ocean straight ahead and lush fruit and greenery to the left and right. Under your breath you whisper "I could get used to this", planning your next trip back already in your mind. The bedroom is pointed directly at the view, a pool, an avocado tree and starfruit tree, and a glorious island paradise lanai. Practical too: laundry, excellent wifi, smart TV, and a full kitchen.

Sep 27 – Oct 4

G$28,642 GYD per night

Guest favorite

Apartment in Kailua-Kona

4.96 out of 5 average rating, 225 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!

Jun 27 – Jul 4

G$32,291 GYD per night

Superhost

Condo in Kailua-Kona

4.86 out of 5 average rating, 136 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.

Nov 27 – Dec 4

G$31,929 GYD per night