Holiday rentals with a pool in Kailua-Kona

A comfortable sleeping area features a spacious queen bed adorned with a white quilt. A cozy sitting area is visible with a light green couch and a small coffee table. Warm light from a lamp illuminates the room, complemented by tropical artwork on the walls.

4.99 out of 5 average rating, 350 reviews

Oceanfront/Hawaiian Charm W/Modern Amenities

Welcome to Hale Kani Moana (House of Ocean Sounds❤️)…the best location, city center on world famous Ali’i Drive. Cozy Hawaiian Charm w/ modern amenities. At your doorstep are the best restaurants, nightlife, and shopping. Stunning oceanfront unit w/sunset views (Fall/Winter). Listen to the ocean waves gently crash as you fall asleep. Fully stocked kitchenette, bathroom/shower, and all the beach equipment you’ll need. FREE Parking+FAST Wifi :-) Note: 3rd (Top Floor) stairs only, no elevators

An expansive saltwater pool is framed by a wooden deck, offering views of the ocean and colorful sunset skies. Tropical foliage partially obscures the scene, adding a serene touch. The tranquil surroundings invite relaxation and peaceful moments.

4.94 out of 5 average rating, 106 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments of your life unfold. Tranquility, privacy, and stunning beauty await you. A masterclass of design in harmony with nature, this exquisite and inspired home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light.

4.92 out of 5 average rating, 100 reviews

A contemporary living space features a sectional sofa adorned with orange accent pillows and a light rug. A wooden coffee table is centered, while a mounted TV sits above a wooden cabinet. Natural light flows in through large sliding doors opening to an outdoor view.

Condo in Keauhou

The Olena at Keauhou Bay

Discover the calm of The Olena, a contemporary 1-bedroom ground floor apartment with A/C, nestled in a quiet complex at the heart of Keauhou in Kailua-Kona. Designed with natural accents and thoughtful details, it is an ideal getaway for 2 guests to enjoy easy walking access to Keauhou Bay and the shops at Keauhou Shopping Center. Enjoy a shared pool, savor sunsets on the expansive lanai with a picturesque view of the Kona Country Club, and immerse yourself in the laid back lifestyle of Hawaii.

A vibrant sunset casts rich orange and purple hues across the sky, reflecting on the ocean's surface. Palm trees frame the view, while soft outdoor lighting accentuates the lush landscaping below. The tranquil scene invites relaxation and contemplation.

4.94 out of 5 average rating, 213 reviews

Aloha Paradise! Remodeled with A/C & Ocean View!

Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

A private lanai is featured with a wooden table and two chairs, overlooking the vibrant blue ocean. Palm trees frame the scene against a clear sky, enhancing the peaceful outdoor setting. Colorful plants in pots add a pop of red to the coastal view.

4.94 out of 5 average rating, 217 reviews

Longboard Studio at Kona Magic Sands Beach

Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

Guest suite in Kailua-Kona

A cozy suite is visible from the entrance, featuring a comfortable full bed dressed with soft linens. A bedside lamp provides warm light, and decorative plants add a touch of nature. The room is complemented by smooth wood flooring and a decorative area rug.

4.96 out of 5 average rating, 167 reviews

Bungalow Bliss Ocean & Pool View

Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, & downtown Kailua-Kona! 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!

An oceanfront sandy beach area is framed by palm trees, with lounge chairs arranged for relaxation. The ocean is visible in the background, with calm waves lapping at the shore. A gated pool area is nearby, enhancing the serene coastal setting.

4.95 out of 5 average rating, 148 reviews

Updated condo with ocean views & air conditioning

Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.

A vibrant tropical garden surrounds a modern villa, nestled within lush greenery and mature palm trees. A serene pool glimmers in the sunlight, creating a peaceful focal point amidst the rich landscaping. The sky above is bright with scattered clouds, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 107 reviews

Suite Magic Sands Beach

Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

The spacious home features natural wood accents, a wide balcony, and large windows that reflect the tropical landscape. Surrounding gardens with lush greenery create a serene atmosphere, while a small pond with a waterfall adds a soothing element to the exterior.

4.99 out of 5 average rating, 160 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.

A vibrant sunset fills the sky with orange and pink hues, contrasted by the silhouette of a historic church with a tall spire. Lush palm trees frame the scene, adding to the tropical atmosphere as the day transitions into evening.

4.95 out of 5 average rating, 207 reviews

Downtown Kona Plaza Condo w/AC

Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

A spacious lanai offers expansive ocean views, framed by lush palm trees. A dining table is surrounded by four black chairs with turquoise cushions. A tropical centerpiece of fruits is placed on the glass table, complementing the outdoor space.

4.96 out of 5 average rating, 163 reviews

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

Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Unbelievable views from the lanai and living room. Top floor corner unit with windows everywhere so you feel like you are living outside. King bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Ocean-front pool with community BBQ. Quiet; set back from Ali'i Drive. Close to everything--just one mile from downtown Kona. Reserved parking spot. AC.

A large lap pool is surrounded by a wooden deck and tropical landscaping. Poolside loungers are positioned for relaxation, with views of the ocean and distant trees. The area is bathed in natural light, creating a serene outdoor atmosphere.

4.97 out of 5 average rating, 200 reviews

Halia Hale

Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

Popular amenities for Kailua-Kona rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 35 reviews

An open-concept living space features a modern kitchen island with seating, surrounded by elegant dining and lounge areas. Large glass pocket doors provide views of the pool area, allowing natural light to brighten the room. Custom furnishings enhance the inviting atmosphere.

Home in Keauhou

Island Time-Luxury Golf Front Home with Pool/Spa

4.9 out of 5 average rating, 157 reviews

The exterior of a modern split-level home is showcased, featuring a spacious pool in the foreground. Tropical palm trees surround the property, while a shaded seating area with an umbrella is visible beside the pool. The expansive deck offers steps leading to the entrance of the home.

Home in Keauhou

Tropical Oasis Home with Pool and Steps to Beach

A serene pool area reflects the vibrant colors of a sunset, with palm trees lining the background. Floating pool loungers are visible, adding a sense of relaxation. The surrounding scenery showcases a tranquil atmosphere, enhancing the peaceful ambiance of the private outdoor space.

4.96 out of 5 average rating, 162 reviews

Private Pool - 180° Ocean View - Minutes to Beach

4.97 out of 5 average rating, 195 reviews

A panoramic view of a lush outdoor space features a vibrant rainbow arching over the landscape. Tropical plants surround a solar heated pool, with lounge chairs positioned nearby. The tranquil setting offers glimpses of the ocean in the background, enhancing the serene atmosphere.

Home in Captain Cook

Tiny House Hawaii

4.94 out of 5 average rating, 245 reviews

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

A private saltwater pool is framed by a spacious patio, featuring lounge chairs and a shaded gazebo. Comfortable seating is provided in the gazebo, enhancing the outdoor living space, while lush greenery and a clear blue sky create a relaxing environment.

4.94 out of 5 average rating, 17 reviews

Clean Stocked Relaxing Kona Home • AC • Pool • BBQ

4.89 out of 5 average rating, 145 reviews

The image showcases a spacious home with a covered second-floor balcony overlooking a heated pool. Lush greenery surrounds the well-maintained lawn, while a few lounge chairs are situated near the water's edge, inviting relaxation. Palm trees and tropical foliage frame the scene.

Home in Waikoloa Village

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

4.98 out of 5 average rating, 240 reviews

A panoramic view of the ocean stretches across the horizon, framed by scattered clouds in a clear blue sky. Lush greenery and rooftops are visible in the foreground, with tall trees adding height to the landscape, creating a serene scene.

Home in Waikoloa Village

Ocean, Sunset, Mountain & Celestial Views

Condo rentals with a pool

A wooden balcony is adorned with several chairs and a telescope positioned toward the ocean. Waves gently crash against the shore, while the sun sets in a gradient of warm colors. Palm trees frame the view, enhancing the serene atmosphere.

4.96 out of 5 average rating, 225 reviews

Discounted A35 Kona Reef Oceanfront AC Park Free

4.92 out of 5 average rating, 183 reviews

An aerial view captures the beachfront property, showcasing a poolside area with palm trees and lounge chairs. The sandy beach extends along the coastline, with sandy areas and ocean waves gently lapping at the shore, while beachgoers enjoy the water and surrounding greenery.

Condo in Kailua

Magic Reef 306 Oceanfront

A peaceful ocean view is captured from the balcony, showcasing the glowing sunset over the water. The tranquil scene is framed by palm trees and reveals a swimming pool overlooking the rocky shore, enhancing the serene coastal atmosphere.

4.86 out of 5 average rating, 209 reviews

Direct-On-Ocean/Walkable inTown/Quiet/PoolElevator

Tall palm trees frame a vibrant sunset over the ocean, with hues of orange and pink blending into the sky. Silhouettes of people can be seen near the water's edge, creating a serene coastal scene.

4.93 out of 5 average rating, 138 reviews

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

4.94 out of 5 average rating, 168 reviews

A dining table is set for four on a private lanai, featuring ocean views framed by swaying palm trees. Plates, glasses, and decorative centerpieces create a welcoming atmosphere for meals by the water, with gentle waves visible in the background.

Condo in Kailua

*Oceanfront Penthouse in Kona with AC!*

An aerial view captures the oceanfront location of Kona Bali Kai, showcasing the building's layout against the vibrant blue water. Waves crash against the rocky shore, while palm trees frame the scene, highlighting the unique coastal setting.

4.88 out of 5 average rating, 440 reviews

☀ Live on the Ocean along Famous Ali'i Drive + ☀

Condo in Waikoloa Village

The cozy sleeping area features a queen bed dressed in crisp white linens, flanked by two bedside tables with lamps. A decorative throw lies across the bed, and plants add a touch of greenery to the room. Natural light filters through the sliding glass doors.

4.97 out of 5 average rating, 154 reviews

Honua Studio *Ocean Views on the Golf Course!

A dining table set for breakfast is situated on the lanai, featuring plates, cups, and a glass with a beverage. In the background, lush tropical greenery and the ocean are visible under a clear blue sky.

4.89 out of 5 average rating, 186 reviews

Kailua Bay Resort - Hale Ho’omaha

Other holiday rentals with a pool

A coastal three-story building is situated beside the ocean, flanked by a line of palm trees swaying gently in the breeze. Waves crash against the rocky shore, while the structure displays a series of balconies overlooking the water.

4.93 out of 5 average rating, 189 reviews

1 BR condo steps from Kona's premier surf break

An open-concept living area features a comfortable gray sofa and a wooden coffee table. The adjoining kitchen showcases dark cabinetry and stainless steel appliances, highlighted by granite countertops. Four bar stools provide seating at the kitchen island, with decorative elements enhancing the space.

4.96 out of 5 average rating, 112 reviews

Centrally Located Downtown Kona Condo

5 out of 5 average rating, 40 reviews

Luxury couple’s retreat w ocean view/AC/king bed

A round wooden coffee table is placed in the foreground, adorned with a small green plant. Behind it, large glass doors offer a panoramic view of the ocean, framed by palm trees, allowing natural light to fill the space.

4.92 out of 5 average rating, 51 reviews

Brand NEW Oceanfront Retreat! Steps to Beach!

A newly remodeled kitchen features soft blue cabinets and quartz countertops. A modern black faucet is positioned over the sink, paired with stainless steel appliances. Decorative plants and art adorn the shelves, while kitchen utensils are neatly arranged, providing a functional yet stylish cooking space.

4.97 out of 5 average rating, 139 reviews

Hawai'i paradise at Kona Isle

Guesthouse in Waikoloa Village

A private outdoor area is showcased with a clear swimming pool and a jacuzzi, both surrounded by a stone patio. A gazebo is positioned nearby, with comfortable seating visible. Lush greenery borders the space, and the sky is partially covered by clouds.

5 out of 5 average rating, 65 reviews

Ohana With Private Pool & Jacuzzi

A bright and airy interior is displayed, featuring a dining table with a bowl of fresh fruit. Comfortable seating arrangements include a light-colored sofa and a chair. Large glass doors open to a scenic ocean view, enhancing the spaciousness of the space.

5 out of 5 average rating, 18 reviews

Stunning Oceanfront Beach Condo!