Vacation rentals with a pool in Kailua-Kona

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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 Kailua-Kona

4.98 out of 5 average rating, 116 reviews

Tropical villa: Heated pool, hot tub & ocean views

Kona House of Palms sits on a private half acre lot in an upscale gated community. Enjoy ocean views and resort-style backyard w/heated pool, waterfall and hot tub. 3-bedroom, 2-bathroom house comfortably sleeps 8 w/ a 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

Guest favorite

The image captures a pristine pool reflecting clear blue skies and palm trees. A gentle gradient of turquoise fills the water, while the ocean is visible in the distance, framed by a secure railing. Lush greenery surrounds the pool area.

Guesthouse in Keauhou

4.88 out of 5 average rating, 144 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 favorite

The image displays a private pool surrounded by a spacious wooden deck, offering expansive ocean views and lush greenery. Several lounge chairs are positioned near the pool, with a large umbrella providing shade. The bright sky emphasizes the inviting atmosphere.

Guest suite in Kailua-Kona

4.96 out of 5 average rating, 138 reviews

Cozy Bungalow Extraordinary Ocean & Pool View

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 favorite

An expansive infinity pool is surrounded by lush landscaping and swaying palm trees. The pool's clear blue water reflects the bright sky, while lounge chairs are placed along the poolside. Nearby, manicured grass areas create a serene atmosphere for relaxation.

Condo in Waikoloa Village

4.94 out of 5 average rating, 126 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 favorite

Home in Kailua-Kona

4.94 out of 5 average rating, 108 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 favorite

A clear blue pool is surrounded by a paved deck with multiple lounging chairs. Lush tropical vegetation and a stone wall provide privacy, while a covered area with an umbrella is visible in the background, adding a shaded retreat. The vibrant greenery enhances the peaceful outdoor setting.

Home in Kailua-Kona

4.89 out of 5 average rating, 171 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 favorite

The outdoor area features a large pool surrounded by tropical landscaping, with palm trees in the background. The two-story home is situated nearby, showcasing expansive windows and an outdoor seating area. Sunlight filters through the trees, creating a serene atmosphere.

Home in Keauhou

4.91 out of 5 average rating, 140 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 favorite

A swimming pool is situated in the foreground, surrounded by tropical foliage. Lounge chairs are positioned poolside, and the two-story house features large windows that invite natural light. The roofline exhibits a distinctive architectural style, contributing to the overall island ambiance.

Home in Kailua-Kona

4.99 out of 5 average rating, 115 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 favorite

A clear blue pool is surrounded by a light-colored concrete deck, with stainless steel handrails leading into the water. Chaise lounges and a shaded seating area are visible nearby, complemented by tropical landscaping along the fence.

Condo in Kailua-Kona

4.93 out of 5 average rating, 107 reviews

Downtown | AC | Pool | Kitchen | Desk |1 Gig | BBQ

º 1 Bed / 1 Bath condo with Pool + Hot Tub, BBQ, A/C, Gig WiFi 6E, Full Kitchen, In-unit Laundry, Patio, pull-out couch + queen air mattress º 5 min walk downtown to restaurants, shops, Ali'i & Kona Pier º Fully stocked and equipped kitchen & bathroom º Desk, chair, 2 monitors, color printer, wired ethernet & Wi-Fi; Full length closet º All beach equipment (chairs, umbrella, towels, snorkels, cooler, body board) º Honda Pilot, Honda HR-V, Honda CR-V or Kia Sportage SX for rent

Guest favorite

A serene pool area is surrounded by lush palm trees and vibrant tropical landscaping. Comfortable lounge chairs are positioned along the pool's edge, inviting relaxation. The clear water reflects a bright blue sky dotted with fluffy clouds, enhancing the tranquil environment.

Condo in Waikoloa Beach Resort

4.96 out of 5 average rating, 132 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 favorite

A shared swimming pool is framed by a wooden deck, situated among lush greenery. Sun loungers are positioned near the pool, which reflects the overcast sky. The ocean is visible in the distance, enhancing the serene atmosphere of the outdoor space.

Condo in Kailua-Kona

4.89 out of 5 average rating, 222 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 favorite

An inviting outdoor space features a sparkling salt water pool with steps leading into the water. Sun loungers are arranged nearby, and a large covered lanai provides ample shaded seating. Lush greenery surrounds the area, creating a peaceful atmosphere.

Guesthouse in Kamuela

4.99 out of 5 average rating, 160 reviews

Kohala Loke Lani, Big Island

Please find us by doing a search for Kohala Loke Lani An expansive ocean and mountain view cottage with a salt water pool located near prime Big Island beaches. This is a large studio ohana that comfortably sleeps two. There are big ocean and mountain views. In the winter months you may even see whales from the lanai! You can follow our adventures on Insta gram at PamelaWonderWoman You can find us by searching for Kohala Loke Lani