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, 351 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

4.95 out of 5 average rating, 186 reviews

Spectacular View, Direct Oceanfront Kona,Top Floor

ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGE Our lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the never ending sound of waves throughout the condo. Enjoy a closet full of essentials for visiting gorgeous beaches on the island. Downtown Kailua-Kona is a short mile walk from the condo, or relax at the oceanfront pool and hot tub!

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.

4.92 out of 5 average rating, 100 reviews

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, 215 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, 219 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

The image captures a rocky beach at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Dark rocks and scattered seashells are visible in the foreground, framed by gentle waves lapping at the shore.

4.97 out of 5 average rating, 153 reviews

Ocean Views~by Honl's Beach~Heart of Kona~AC

ENJOY OCEAN VIEWS from a newly renovated Stylish condo in one of Kona's most desirable locations. Condo is an apx 6 to 8 min walk to a variety of Ocean Side Restaurants, entertainment and a quick walk to Honl's Beach. No rental car is needed as you are a short walk into town. The condo looks directly out to the Pacific Ocean and is on the ground floor so (no long stairs to climb). Free dedicated parking spot, which is so IMPORTANT in KONA now! 65" SMART TV, AC, the SOFA folds to a 2nd bed.

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, 169 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.

4.96 out of 5 average rating, 108 reviews

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.

Apartment in Kailua-Kona

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.

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, 208 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, 165 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 modern living area is presented with a comfortable sofa and armchair, complemented by a light wooden coffee table. A large television is positioned opposite the seating. Floor-to-ceiling windows provide views of the ocean, allowing natural light to fill the space.

4.92 out of 5 average rating, 232 reviews

Blissful paradise with epic view- Hale Mahana

Serenity in Kona- with epic ocean views! Wake up with the ocean waves crashing below. Hang out on the lanai with some Kona coffee from the Green Flash cafe next door. You have a front row seat for whale watching during whale season. Or, hang out and enjoy the sunsets- at times with our local manta ray! We have a queen sofa bed, and AC. Close to town- an 18 minute walk. Quiet, very little road noise here. You can rent bikes too across the street.

Popular amenities for Kailua-Kona rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 112 reviews

An inviting outdoor space features a private pool surrounded by lush tropical plants. The soft glow of pool lighting highlights the stone patio, while lounge chairs are positioned for relaxation. Tall palm trees are visible against a colorful evening sky.

Home in Keauhou

Mollie’s Paradise Resort Home & Private Pool

The image captures a panoramic view of a private heated swimming pool surrounded by lush greenery. Lounge chairs are positioned around the pool, and a shaded gazebo adds to the outdoor space. In the background, the vibrant blue ocean stretches under a clear sky.

4.99 out of 5 average rating, 101 reviews

Exceptional Oceanview Home - Pool & Stunning View

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, 162 reviews

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

4.91 out of 5 average rating, 158 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, 246 reviews

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

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, 107 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

Condo rentals with a pool

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 modern kitchen is visible, featuring white cabinetry, sleek black appliances, and a glossy countertop. A dining area with bar seating is positioned near a cozy living space, which includes a light-colored couch and large ottoman, complemented by soft lighting along the walls.

4.96 out of 5 average rating, 282 reviews

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

A serene lanai is displayed with a view of a vibrant sunset. Lush greenery frames the scene, with palm trees and blooming flowers visible. Soft lighting is strung along the railing, adding a warm touch to the outdoor space designed for relaxation.

4.87 out of 5 average rating, 122 reviews

Keauhou Garden - Ocean view - Walk to Harbor

An expansive view of the ocean at sunset captures vibrant oranges and yellows illuminating the sky. A community pool is visible in the foreground, surrounded by lounge chairs. Lush palm trees frame the scene, enhancing the tropical ambiance.

4.89 out of 5 average rating, 220 reviews

Ali'i Dr w/ Ocean Sunsets next to Farmer's Market

An outdoor area is presented with a spacious pool surrounded by lounge chairs and umbrellas. A wooden gazebo offers shaded seating, with palm trees framing the view. Sunlight casts a warm glow over the scene, enhancing the vibrant greenery and tranquil atmosphere.

4.88 out of 5 average rating, 181 reviews

Kona Getaway at Kahalu'u Bay 2 Bed 2 Bath Condo

The open living space features a comfortable sofa and a dining area with a round table, set against a backdrop of expansive ocean views. Light streams through large windows, with tropical decor highlighting the serene atmosphere.

4.91 out of 5 average rating, 256 reviews

Direct Oceanfront - Magic Sands Beach!

A small balcony table is set for two, featuring woven chairs. A simple arrangement of greenery sits in the center. The backdrop reveals the ocean with gentle waves and palm trees swaying in the breeze, under a bright blue sky.

4.9 out of 5 average rating, 140 reviews

Ocean Front Corner Condo in Paradise

Lush greenery surrounds a serene view of the ocean, framed by tall palm trees. A low building with a tiled roof is visible in the foreground, emphasizing the tropical landscape under a clear blue sky.

4.93 out of 5 average rating, 116 reviews

Hawaii Retreat with Beautiful Ocean View and AC

Other holiday rentals with a pool

5 out of 5 average rating, 35 reviews

A spacious living area features a large window offering unobstructed views of the ocean and coastline. A light-colored sofa is positioned beside a wooden coffee table. The serene blue water and distant palm trees are visible beyond the balcony.

Apartment in Kailua-Kona

Gorgeous Unit, Stunning Views!

4.8 out of 5 average rating, 191 reviews

A serene ocean view is displayed at sunset, with golden light reflecting on the water. Tropical palm trees line the shore, framing the scene. The sound of waves gently crashing is heard in the background, enhancing the tranquil atmosphere.

Apartment in Kailua-Kona

WAVES! WAVES! ON THE OCEAN! BOUTIQUE COMPLEX

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, 52 reviews

Brand NEW Oceanfront Retreat! Steps to Beach!

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, 19 reviews

Stunning Oceanfront Beach Condo!

5 out of 5 average rating, 32 reviews

Apartment in Keauhou

NEW! ADORABLEbungalow in Kona

A tranquil ocean view captures a stunning sunset, where vibrant hues of orange, pink, and purple blend across the sky. The calm waters reflect these colors, creating a serene atmosphere. Dark rocks frame the scene, enhancing the natural beauty of the coastal landscape.

4.98 out of 5 average rating, 47 reviews

1BR Kona Condo w/ Chef’s Kitchen & Tropical Lanai

A spacious lanai is furnished with a round table and four black wicker chairs, providing a comfortable space for dining. A sectional bench with patterned cushions enhances the area. Lush greenery and ocean views are visible through large windows, with palm trees swaying softly in the background.

5 out of 5 average rating, 38 reviews

Brand new Luxury Oceanfront Living in Kona with AC

Superhost

A spacious bed is adorned with patterned bedding and a decorative yellow pillow. Framed by two pendant lights, a nature-themed artwork hangs above the headboard. A bench with tufted upholstery is positioned at the foot of the bed, complementing the room's serene design.