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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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Home in Waikoloa Village

4.71 out of 5 average rating, 104 reviews

Wonderful Community Home Close to Famous Beaches

Spacious home with AC, located 15 min away from the famous beaches, 5 min away from shopping centers & tons of activities close by Sleeps up to 8 people and an additional option to sleep up to 9 people (please inquire how). You can swim in the community pool, play tennis or play golf (small fee) on our gorgeous course. (driving distance) No Pets or smoking allowed. Kids Deposit Required.Guest must adhere to the community quiet hours of 8pm to 8am. Large group require deposit.Host lives on site.

Guesthouse in Keauhou

4.88 out of 5 average rating, 137 reviews

180 degree ocean view, private pool

Family friendly, NON SMOKING PROPERTY has a cottage with a 180 degree ocean view & beautiful pool. Enjoy incredible sunsets from the large deck, outdoor showers in the ginger garden & relaxing evenings in the hot tub. We welcome guests of all Races, religions, and sexual orientation! THERE IS NO LIFEGUARD ON DUTY NO DIVING IN THE POOL PLEASE THE SLIDE IS FEET FIRST ONLY! WE INVITE YOU TO PLEASE READ THROUGH THE FOLLOWING SECTION AS THERE IS OTHER PERTINENT INFORMATION FOR YOU AND YOUR FAMILY

Condo in Waikoloa Village

4.95 out of 5 average rating, 120 reviews

Casa Chilin 2bd/2bth@Waikoloa Resort Walk To Beach

Aloha and thank you for considering our home for your visit to the Big Island of Hawaii. Our recently remodeled 2bd/2bath home is walking distance from Shopping (Kings/ Queens Shops), Dining, Entertainment, A’ Bay Beach, Historic Sites. The home is stocked with all your basic necessities. 1 covered parking spot included, steps from home. Great location for couples, groups, families with kids, everyone is welcome! Enjoy the sunset and trade wind breeze from the lanai. Washer and dryer in unit.

Home in Kailua-Kona

4.98 out of 5 average rating, 108 reviews

Private tropical villa: Pool, Hot Tub & Ocean view

Kona House of Palms sits on a very private half acre lot in a gated community. Enjoy ocean views and resort-style backyard with pool, waterfall and hot tub. 3-bedroom, 2-bathroom house comfortably sleeps 8 with the sofa bed in the common area. Lush greenery keeps yard, pool and hot tub very private. Fast Internet, smart TVs, plenty of linens, well-stocked kitchen, beach chairs, pool toys and much more is provided. Everything you need to enjoy you stay is HERE. Fully licensed: STVR-19-365351

Home in Kailua-Kona

4.94 out of 5 average rating, 103 reviews

Tropical Private Oasis, Heated Pool & OceanView!

3 bedroom/2.5 bath, Sleeps 8 with Private Solar Heated Pool with Waterfall, Lanai, Gazebo with Ocean View, Tropical Yard. 5 min to downtown Kona along the water. This "model home" sits in a gated community of Kahakai with breathtaking views. It has all upgrades throughout the house for ultimate luxury. A pathway on this 1/2 acre plus property leads to an elevated private gazebo for that amazing romantic evening dinner or relaxing with your special one while looking at an amazing ocean view.

Home in Kailua-Kona

4.89 out of 5 average rating, 167 reviews

My Kona Paradise

Taxes included in the nightly price. Check our specials by date! Corona Virus Update: Please note that we have taken additional steps to make sure the home is not only clean but sanitized. The remote controls, doorknobs and all surfaces are all wiped down with antiseptic solution. We also send the laundry out to a professional service and is sanitized. We want you to be assured that we are doing everything we can to make sure you have a wonderful time in our home. STVR information below.

Home in Keauhou

4.9 out of 5 average rating, 134 reviews

Tropical Oasis Home with Pool and Steps to Beach

Experience this tropical oasis, conveniently located in Keauhou. With a 2 minute walk to the ocean - watch the breathtaking sunset, stargaze at night , and fall asleep to the ocean waves crashing into Heeia Bay! Awake to the wild song birds as you sip on your Kona coffee, and plan your Big Island adventure. Enjoy an afternoon cocktail by the pool, perfect for yoga, reading a book, or cooling off. Walk 5 minutes to nearby delicious restaurants, or a 10 minute drive to downtown Kona.

Home in Kailua-Kona

4.99 out of 5 average rating, 108 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai and Balinese architecture, and ornate, hand-carved wood. Floor-to-ceiling windows and skylights showcase the beauty of the Big Island. The kitchen and living rooms connect to spacious bedrooms with a covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a cooler breeze than busy downtown while not being far from the action.

Condo in Waikoloa Beach Resort

4.97 out of 5 average rating, 124 reviews

Enjoy lush tropical lifestyle in Waikoloa Resort

Enjoy your stay at this serene ground floor, remodeled in 2023, 1 bedroom 1 bath corner unit condominium in one of the best location of Waikoloa Beach Resort. * Lush tropical landscaping with ponds and waterfalls * Next to pool, tennis court, BBQ and fitness center * Walk to beach, shops, restaurants, entertainments and Grand Hilton * Free fast WiFi. Central A/C. Washer and dryer. * Spectrum Cable and Roku streaming TVs * Private Parking spot 50 yards from the front door

Condo in Kailua-Kona

4.89 out of 5 average rating, 214 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.

Rental unit in Kailua-Kona

4.93 out of 5 average rating, 222 reviews

Great Location, In Town, Modern and Clean

Great condo, right in town. Walk to the beach, shops, and restaurants. Newly remodeled condo, furnished with full kitchen and in unit washer and dryer. Fast wifi, air conditioning, and beach equipment for your use. You don't need a rental car, and you can enjoy the pool, hot tub, and BBQ area as well. Free parking stall included, you can walk to most restaurants and shops on Alii drive without having to pay the parking fees.

Rental unit in Captain Cook

4.83 out of 5 average rating, 209 reviews

Tropical Hideaway w/ Pool, Hot Tub

Tropical Hideaway is a charming Hawaii-style downstairs studio apartment in a lush garden setting, with ocean views, a salt swimming pool with waterfall, & private hot tub--just three minutes away from fabulous snorkeling, kayaking & diving experiences. The Hawaii accommodation tax of 18% will need to be paid upon arrival (no place to add it in Airbnb's pricing). No kids under 10, renters must be 25 or older.

Vacation rentals for every style

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Popular amenities for Kailua-Kona rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Keauhou

5 out of 5 average rating, 74 reviews

Mollie’s Paradise Resort Home - No Cleaning Fee!

Home in Waimea

5 out of 5 average rating, 10 reviews

PiH ~ Flora Paradise ~ Hilton Passes Included

Home in Kailua-Kona

4.95 out of 5 average rating, 151 reviews

Private Pool - 180° Ocean View - Minutes to Beach

Home in Waikoloa Village

4.88 out of 5 average rating, 132 reviews

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Home in Kailua-Kona

5 out of 5 average rating, 40 reviews

Tropical paradise, heated pool, ocean views, AC

Home in Kailua-Kona

4.97 out of 5 average rating, 180 reviews

Halia Hale

Home in Kailua-Kona

4.96 out of 5 average rating, 50 reviews

Lush Kona Home • Pool • Lanai • Fully Equipped

Home in Kailua-Kona

4.8 out of 5 average rating, 54 reviews

Luxury Gated Estate - AC, Pool, Near Magic Sands

Condo rentals with a pool

Condo in Keauhou

5 out of 5 average rating, 39 reviews

Newer furnished 3 Bed/2 Bath Condo with Ocean View

Condo in Kailua-Kona

4.94 out of 5 average rating, 53 reviews

Kona by the Ocean

Condo in Kailua-Kona

4.93 out of 5 average rating, 132 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

Condo in Kailua-Kona

4.96 out of 5 average rating, 24 reviews

Bohemian style 2 bedroom, 2 bath condo

Condo in Kailua-Kona

4.94 out of 5 average rating, 72 reviews

Oceanfront complex at Casa de Emdeko unit #102

Condo in Kailua-Kona

4.78 out of 5 average rating, 114 reviews

Beach Paradise

Condo in Kailua-Kona

4.94 out of 5 average rating, 72 reviews

Oceanfront 2 bed, 2 bath, kitchen with full AC!

Condo in Kailua-Kona

4.97 out of 5 average rating, 127 reviews

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!

Quick stats about vacation rentals with a pool in Kailua-Kona

Total rentals
1.6K properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
50K reviews
Family-friendly rentals
780 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
890 properties have a dedicated workspace

Destinations to explore