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, 377 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, 188 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 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.

4.95 out of 5 average rating, 224 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 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, 145 reviews

Ocean Front Corner Condo in Paradise

Tranquil ocean front setting is pure relaxation listening to the waves. Enjoy ocean breezes & expansive views, w/dolphins, whales & gorgeous sunsets from a private corner unit balcony! Step to the beachfront & snooze under a palm tree. BBQs & picnic tables right on the beach. Solar heated saltwater pool. Also a saltwater pool filled by surf crashing in to swim in! Explore tidal pools in front. Walk to restaurants, shops, beaches & snorkeling. Get the trolley next door & ride share bikes close

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.

4.97 out of 5 average rating, 177 reviews

Bungalow Bliss Kona - 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!

A spacious lanai overlooks the ocean, featuring two blue chairs and a woven lounge chair. Lush palm trees sway gently in the breeze, while waves crash against the shore in the background. A geometric-patterned rug adds a touch of comfort to the outdoor space.

4.97 out of 5 average rating, 119 reviews

Discounted KonaReef D33 OceanFront* AC* Park Free*

The Kona Reef is being renovated in 2026. Check out our special construction rates. Reno hours 8a-5p Mon-Sat while you are out at the beaches, volcano etc. You’ll love this condo! Absolute Ocean Front. 5 minute walk to downtown. Free parking! Completely remodeled! Fresh, clean, stylish & comfortable. NEW Full A/C, Stocked Kitchen & Beach & Golf Equipment. ATTENTION GOLFERS! 2 sets of Callaway Clubs! Check out our 2 other Kona Reef condos A35 & B31 TA-109-936-6880-01 STVR-19-352037

4.95 out of 5 average rating, 242 reviews

Oceanfront Gem, Walk to Beach/Town, AC, Elevator

Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

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.

4.96 out of 5 average rating, 159 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, 118 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.

Superhost

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.

Condo in Keauhou

4.87 out of 5 average rating, 127 reviews

Keauhou Garden - Ocean view - Walk to Harbor

Stunning ocean views, walking distance to the harbor and shopping center. Keauhou Garden is a clean and cozy stay at the heart of Keauhou, one of the best neighborhoods to stay on Big Island. Peaceful and quiet place, yet just a short drive from Kona downtown. A perfect place to unwind and relax while admiring beautiful views of the ocean and the golf course. Keauhou Resort is nestled next to the Kona Country Club, a spectacular public golf course with breath-taking ocean views.

A tranquil pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant foliage. Lounge chairs are placed around the pool, where guests are seen enjoying the water and the sunny environment. The two-story building with balconies is visible in the background.

4.9 out of 5 average rating, 472 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Guest suite in Kailua-Kona

A spacious bedroom features a wooden bed with a neatly made light-colored quilt, accented by colorful pillows. A decorative rug covers the floor, and a ceiling fan is visible above. A small table and a shelving unit filled with essentials are present, creating a functional space.

4.96 out of 5 average rating, 169 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

Popular amenities for Kailua-Kona rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 118 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, 102 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.

4.98 out of 5 average rating, 174 reviews

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

4.96 out of 5 average rating, 113 reviews

A private outdoor space features a pool surrounded by tropical greenery and stone pathways. The two-story home is visible in the background, showcasing a deck with shaded seating. Solar panels are installed on the roof, and the ocean is seen in the distance under a clear sky.

Home in Keauhou

Kahaluu Bay Get-Away

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, 169 reviews

Private Pool - 180° Ocean View - Minutes to Beach

4.91 out of 5 average rating, 165 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

4.98 out of 5 average rating, 202 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

4.93 out of 5 average rating, 258 reviews

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

Condo rentals with a pool

A comfortable living area features floral-patterned sofas, with large windows offering unobstructed ocean views. The gentle waves can be seen breaking on the rocks outside. A wooden coffee table is centered on a patterned rug, while an outdoor dining area is visible on the balcony.

4.9 out of 5 average rating, 144 reviews

Oceanfront living - Floor to Ceiling wall of glass

Condo in Waikoloa Village

A clear view of a community pool surrounded by palm trees, with lounge chairs set up on the side. The sun shines brightly on the water, creating a refreshing atmosphere. In the background, a clubhouse structure is visible, enhancing the poolside experience.

4.95 out of 5 average rating, 149 reviews

Condo with A/C, Pool, Spa & Golf Course Views

A vibrant sunset casts shades of orange and pink across the sky, reflecting off the water. Silhouetted palm trees and surrounding buildings frame the scene, while warm glow from outdoor lights below adds to the tranquil atmosphere.

4.9 out of 5 average rating, 110 reviews

TOP FLOOR, OCEAN VIEW, INCREDIBLE LOCATION

A view from the lanai features lush green vegetation in the foreground with a glimpse of the ocean in the background. The landscape is dotted with palm trees and includes nearby buildings, showcasing a peaceful setting.

4.84 out of 5 average rating, 334 reviews

Kailua Village Condo in the Heart of Kona

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, 298 reviews

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

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, 146 reviews

Hawai'i paradise at Kona Isle

4.93 out of 5 average rating, 177 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!*

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, 121 reviews

Hawaii Retreat with Beautiful Ocean View and AC

Other holiday rentals with a pool

4.85 out of 5 average rating, 53 reviews

Guest suite in Keauhou

Comfortable, Relaxing Poolside Retreat

A wooden table is set on a balcony, featuring two plates and glasses, with a decorative arrangement of flowers. The ocean view is framed by palm trees and greenery, creating a serene backdrop for dining.

4.86 out of 5 average rating, 100 reviews

10 min to Town* AC*King Bed*Oceanside Pool

5 out of 5 average rating, 56 reviews

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

Superhost

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.

4.9 out of 5 average rating, 264 reviews

Direct Oceanfront - Magic Sands Beach!

5 out of 5 average rating, 39 reviews

Apartment in Keauhou

NEW! ADORABLEbungalow in Kona

Superhost

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, 61 reviews

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

A welcoming living space features a comfortable leather sofa and a wooden coffee table, accompanied by decorative accessories. Nearby, a TV is positioned on a contemporary cabinet. Natural light enters through large sliding doors, with a view of a lush green area. A bathroom entrance is visible in the background.

4.87 out of 5 average rating, 31 reviews

Beach Access: Peaceful 1 Bed Condo in Kailua-Kona

A spacious balcony offers expansive ocean views, featuring a comfortable seating area with a hanging chair and a small table. The serene waters and coastal scenery create a peaceful atmosphere, inviting relaxation and enjoyment of the surroundings.