Top Kailua-Kona rentals with pool or private pool - Hawaii

Explore Kailua-Kona rentals with pools

Showing deals for: Oct 18 - Oct 21

Kona Bali Kai

Sleeps 4 · 1 bedroom

CA $1,108 total

includes taxes & fees

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Sleeps 12 · 5 bedrooms · 4+ bathrooms

CA $5,805 total

includes taxes & fees

2BR/2BA Kona Reef Ocean & White Sand Beach From Every Room

Sleeps 6 · 2 bedrooms · 2 bathrooms

CA $2,641 total

includes taxes & fees

Top rated rentals with pools - Kailua-Kona

Premier Host

Spectacular time in a perfect place on the Big Island!!

Excellent location, all amenities close-by with well stocked condo, good quality appliances, comfortable and roomy, beautiful views with ocean right out doorstep, lovely pool...market 2 mins away...fresh fruit, macadamia nuts, Coffee, chocolate..yay!!!Love, love this place!! Mahalo

Darcy P.

Stayed Apr 2025

Enjoy this aquarium at your fingertips. BEST VIEW IN KONA!

Premier Host

Honk Hideawau

Lived up to billing, well appointed and clean. Great to be situated over the black rocks with the surf crashing in while watching a beautiful sunset.

Bob P.

Stayed Feb 2025

Premier Host

Perfect Kona Getaway: Beautiful Condo & Amazing Host!

I had an incredible stay at this Kona VRBO condo! The location was perfect—just minutes from the beach, local shops, and great dining. The condo itself was spotless, spacious, and had everything I needed for a comfortable stay. The highlight was definitely the host—they went above and beyond to ensure I had everything I needed and even gave some great local recommendations. Their hospitality really made the trip extra special. Highly recommend this place if you're looking for a relaxing and hassle-free getaway!

Colin H.

Stayed Jan 2025

Premier Host

Amazing View

This property did not disappoint. The location was perfect and the view was amazing. We will be back!

Candy M.

Stayed Jan 2025

Premier Host

Absolutely incredible!

The view from the lanai was so beautiful, we never wanted to leave! We really appreciated the comfy lounge chairs and made good use of them watching the dolphins and surfers all day long. Beds were extremely comfortable and the unit has all you would need for a trip to the beach to preparing meals in the fully stocked kitchen. Yes, the unit has not been updated but everything was in excellent repair and very clean and and comfortable and that is all that mattered to us! As amazing as this unit was the best part of this rental were the owners Jim and Nancy. Their communication with us was the best we have ever encountered in all our years of renting. Their obvious dedication to ensuring our stay was perfect was so appreciated and we loved the mid stay information email we received from them-so fun! Thank you for an awesome stay, we will be back!

Donalda (Dawn) S.

Stayed Nov 2024

Right on the ocean! Watch dolphins and surfers from the spacious lanai.

Premier Host

Great place and location

The place was great and equipped with good beach chairs/umbrella. Unbeatable location close to restaurants but still quiet.

Jessica Alix M.

Stayed Mar 2024

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Frequently asked questions

Are there any vacation rentals with a pool in Kailua-Kona?

Pick one of our 2,144 vacation rentals with a pool in Kailua-Kona and get ready for cannonball contests. Holualoa Village, Alii Heights Mauka and Kona Palisades are some of the city's most popular areas to stay.

How much does it cost to stay in a vacation rental with a pool in Kailua-Kona?

Exactly where you stay, when you decide to travel and your trip length will influence the price of a vacation rental with a pool in Kailua-Kona. Key in your travel dates on Vrbo, then pick the right one for you and prepare to make a splash.

When is the best time to book a vacation rental with a pool in Kailua-Kona?

Vrbo makes it easy to find a vacation rental with a pool in Kailua-Kona whenever you prefer to go. Begin by considering the weather conditions for the time of year you're thinking of traveling. If you're vacationing in the high season, book early for the best availability.

What vacation rentals with a pool in Kailua-Kona have nice views?

Vrbo makes it easy to find a stay with impressive views and access to poolside recreation. Just use our "Location" filter to narrow down the type of area you prefer to be in, and the scenery you like to stare out at, while searching for vacation rentals with a pool in Kailua-Kona.

Are there vacation rentals with a private pool in Kailua-Kona?

Pick a vacation rental with a private pool in Kailua-Kona and go for a refreshing morning swim or late-night soak — or whenever the mood strikes! You'll be able to keep your kids easily occupied, and you won't have to worry about sharing with other guests. Use our "Private pool" filter to find your ideal vacation rental.

What are the top things to do in Kailua-Kona?

Get your Kailua-Kona escape off to a terrific start by heading to top-rated sights like Captain Cook Monument, Hulihee Palace and Magic Sands Beach. Stay in a Vrbo vacation home rental with the family and then uncover this destination's wonders together.

Why should I book my vacation rental with a pool with Vrbo?

Booking your vacation rental with a pool with Vrbo means you'll have the whole place for your exclusive use — your own private space to make a splash with no interruptions or distractions from anybody else. What's more, our easy payment and cancellation policies allow you to alter your plans if you need to.

Rental Ideas

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Explore Kailua-Kona rentals with pools

Kona Bali Kai

Hale Kona Kai by Casago Kona

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

2BR/2BA Kona Reef Ocean & White Sand Beach From Every Room

Royal Sea Cliff Kona by OUTRIGGER

Aston Kona by the Sea

Top rated rentals with pools - Kailua-Kona

Spectacular time in a perfect place on the Big Island!!

Honk Hideawau

Perfect Kona Getaway: Beautiful Condo & Amazing Host!

Amazing View

Our thoughts on D35 at Kona Reef

Absolutely incredible!

Awesome Place

Great place and location

Find spaces that suit your style

Peace of mind

More quality time

All the privacy of home

More for less

Frequently asked questions

Rental Ideas

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