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Vacation rentals with a pool in Island of Hawai'i

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Island of Hawai'i

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, 105 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.

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.

Guesthouse in Kailua-Kona

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

Guesthouse in Keaau

4.94 out of 5 average rating, 175 reviews

Adorable Jungle Retreat Cabin with Pool

You awaken to birdsongs that rival the first spring on earth. A gentle rain falls, casting a silence over the cozy cabin. Do you stay in bed a little longer and soak up this soothing soundtrack of white noise? Or do you wake yourself up with a cup of Hawaiian coffee and an outdoor shower? Or maybe you start your day with a float and yoga. Whether you are looking for a quiet place to get a good night’s rest, a solo escape into nature, or a romantic getaway for your honeymoon, this is the place.

Home in Kailua-Kona

4.98 out of 5 average rating, 109 reviews

Private tropical villa: Pool, Hot Tub & Ocean view

Kona House of Palms sits on a private half acre lot in an upscale gated community. Enjoy ocean views and resort-style backyard w/ 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 Pepeekeo

4.86 out of 5 average rating, 158 reviews

Hamakua Coast Tropical Home

A beautiful tropical style custom home featuring private ocean views and a small gated pool. Our home was thoughtfully designed to maximize Hawaiian indoor/outdoor living and entertaining in a manicured park-like setting. A palm lined driveway leads you to a single level 3 bedroom, 2 1/2 bath residence located in the exclusive Pepeekeo Point subdivision, approx. 15 minutes from Hilo. Featuring a fiberglass pool with a bamboo pavilion& bbq for outdoor dining No parties or unregistered guests

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 Kailua-Kona

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.

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.

Condo in Waikoloa Beach Resort

4.97 out of 5 average rating, 126 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

Rental unit in Kailua-Kona

4.92 out of 5 average rating, 224 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.

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Popular amenities for Island of Hawai'i rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Keaau

4.94 out of 5 average rating, 16 reviews

Gated Retreat Near The Ocean w/ Pool & Large Deck!

Home in Keaau

4.91 out of 5 average rating, 11 reviews

Kaloli Sunrise 2BR Private Pool Sleeps 5 Near Hilo

Home in Kailua-Kona

4.95 out of 5 average rating, 152 reviews

Private Pool - 180° Ocean View - Minutes to Beach

Home in Kailua-Kona

4.94 out of 5 average rating, 228 reviews

Classic Kona 🤙🏻 \\ Epic Ocean View 🌊 \\ Pool 🏊

Home in Waikoloa Village

4.88 out of 5 average rating, 133 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 Holualoa

4.99 out of 5 average rating, 150 reviews

"Aolani House" Resort Style Home w/ Infinity Pool

Condo rentals with a pool

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, 133 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

Condo in Kailua-Kona

4.95 out of 5 average rating, 74 reviews

Oceanfront complex at Casa de Emdeko unit #102

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!

Condo in Naalehu

4.87 out of 5 average rating, 107 reviews

Turtle Paradise at Punalu'u Black Sand Beach

Condo in Kailua Kona

4.67 out of 5 average rating, 9 reviews

Kona Makai 3-203

Condo in Waikoloa Village

4.82 out of 5 average rating, 72 reviews

Newly renovated, top floor 2 BR condo w/ pool/spa

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