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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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Condo in Kailua-Kona

4.82 out of 5 average rating, 111 reviews

Steps to ocean,surfing /5 Min to downtown/Central

KEEP IT REAL: This is a cozy smaller complex with a family feeling. It's not a fancy resort. View: This is NOT an ocean view unit. The unit faces a wooded area. Noise: You can hear waves, island roosters, and occasional cars. This is a condo, so potentially. You can hear the other tenants. Bugs: We are on a tropical island. Occasionally you will see ants and bugs around. Want to wake up to the sound of the waves crashing less than 100 yards away? The condo is across the street from the ocean

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 128 reviews

Cozy Island Bungalow in Kailua-Kona

Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, downtown Kailua-Kona, etc. Sun-kissed ocean & pool views await you in this cozy, stylish space. A perfect budget-friendly, clean, cool place to rest between your island adventures. Located near downtown Kailua-Kona and 500 ft above sea level, this property offers cooler temperatures and breezes that delight guests. This suite best fits solo travelers or couples who like to be cozy.

Guest favourite

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

Guest favourite

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.

Guest favourite

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.

Guest favourite

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.

Guest favourite

Home in Keauhou

4.9 out of 5 average rating, 135 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.

Guest favourite

Home in Kailua-Kona

4.99 out of 5 average rating, 109 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.

Guest favourite

Condo in Waikoloa Beach Resort

4.97 out of 5 average rating, 125 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

Guest favourite

Condo in Kailua-Kona

4.89 out of 5 average rating, 216 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.

Guest favourite

Rental unit in Kailua-Kona

4.92 out of 5 average rating, 223 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, 211 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.

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Popular amenities for Kailua-Kona rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Keauhou

5 out of 5 average rating, 75 reviews

Mollie’s Paradise Resort Home - No Cleaning Fee!

Guest favourite

Home in Waikoloa Village

4.88 out of 5 average rating, 101 reviews

Island Views Hale

Guest favourite

Home in Kailua-Kona

4.95 out of 5 average rating, 152 reviews

Private Pool - 180° Ocean View - Minutes to Beach

Guest favourite

Home in Captain Cook

4.97 out of 5 average rating, 175 reviews

Tiny House Hawaii

Guest favourite

Home in Kailua-Kona

5 out of 5 average rating, 40 reviews

Tropical paradise, heated pool, ocean views, AC

Guest favourite

Home in Waikoloa Village

4.98 out of 5 average rating, 184 reviews

Ocean, Sunset, Mountain & Celestial Views

Guest favourite

Home in Kailua-Kona

4.97 out of 5 average rating, 180 reviews

Halia Hale

Guest favourite

Home in Kailua-Kona

4.96 out of 5 average rating, 50 reviews

Lush Kona Home • Pool • Lanai • Fully Equipped

Condo rentals with a pool

Guest favourite

Condo in Kailua-Kona

4.94 out of 5 average rating, 53 reviews

Kona by the Ocean

Condo in Kailua-Kona

4.85 out of 5 average rating, 158 reviews

Luxury in the Heart of Kona

Guest favourite

Condo in Kailua-Kona

4.98 out of 5 average rating, 226 reviews

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

Guest favourite

Condo in Kailua-Kona

4.92 out of 5 average rating, 112 reviews

Oceanfront Condo/Hawaiian Style. 1Bd, w/AC & Wifi

Condo in Kailua-Kona

4.76 out of 5 average rating, 252 reviews

Oceanfront Condo-Paradise

Condo in Kailua-Kona

4.82 out of 5 average rating, 189 reviews

Cozy Kona Condo on Ali'i drive Ocean View Pool

Condo in Kailua-Kona

4.78 out of 5 average rating, 115 reviews

Beach Paradise

Condo in Kailua-Kona

4.9 out of 5 average rating, 104 reviews

Newly renovated, ocean view, steps from downtown.

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

Total rentals
1.6K properties
Nightly prices starting at
$70 CAD 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