Holiday rentals with a pool in Kailua-Kona

A spacious sleeping area features a large bed dressed with neatly arranged white linens and towels. Soft lighting from bedside lamps complements the artwork depicting a coastal sunset on the wall. A full-length mirror reflects the room's inviting ambiance.

4.94 out of 5 average rating, 137 reviews

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

º 1 Bed / 1 Bath 682 sq ft 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 Local recommendations & island guidebook 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 6 vehicles available for rent

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.

4.95 out of 5 average rating, 110 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.

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, 216 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, 220 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

A private solar heated pool is surrounded by tropical landscaping, featuring a waterfall cascading over black rocks. Comfortable outdoor seating is arranged nearby, with vibrant plants adding color and lushness to the serene atmosphere.

4.95 out of 5 average rating, 132 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.

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, 151 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 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, 216 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.

Guest suite in Kailua-Kona

A spacious outdoor lanai features a large umbrella providing shade over glass-top tables and bright teal chairs. The stunning ocean view is visible in the background, along with a beautifully maintained pool and lush greenery surrounding the area.

4.98 out of 5 average rating, 315 reviews

Poolside Studio🤙🏻Ocean View / AC / King🛌10min➡️Beach

A gorgeous remodeled studio featuring an ocean view lanai with a pool right outside. The lanai has a huge umbrella and bbq, and is a fully enclosed dining area with a self-closing gate to keep your kids safely away from the pool. The interior is all freshly renovated in 2020 with stylish and comfortable furniture. Covered parking is steps from the entry and plenty of quality beach gear is available for you to use anytime. Ice-cold A/C and Apple TV make relaxing inside just as nice.

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, 167 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, 236 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.

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, 283 reviews

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

This luxurious condo with custom interior design is located in historic downtown Kona from where you can walk to sandy Kailua Bay beach just 2 blocks away, restaurants, supermarket, shopping and entertainment. The condo features: pool with BBQ deck, private laundry, full kitchen with dishwasher and ice maker, two zoned ultra quiet AC, Cal. King bed, a screened-in Lanai with peekaboo view of the ocean, fiber optic internet, and a 65” 4K smart TV!

A spacious interior showcases a king bed with soft linens, positioned to offer views of the ocean through large sliding glass doors. A dining area with bar stools overlooks the water, while light drapes frame the windows, enhancing the coastal ambiance.

4.98 out of 5 average rating, 170 reviews

NEW! UNIQUE Top floor Oceanfront Magic Sands Beach

Aloha! Location, Location, Location! + NEWLY Remodelled interior & has A/C! This unique oceanfront is located on the TOP floor of Kona Magic Sands condominiums. It features A/C, brand NEW stainless steel appliances (Full kitchen & Dish Washer). The honest, elegant and minimal interior design of this space quietly invites in the majestic Pacific Ocean and its breathtaking sunset views. THE VIEW! THE DESIGN!

Popular amenities for Kailua-Kona rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a 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

4.96 out of 5 average rating, 111 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

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, 163 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, 249 reviews

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

5 out of 5 average rating, 35 reviews

A spacious living area showcases stylish furnishings, including a mix of light-colored sofas and accent pillows in vibrant hues. A wooden coffee table occupies the center, while large sliding glass doors open to reveal panoramic ocean views. Wood beams create a warm and inviting ceiling.

Home in Keauhou

Panoramic Ocean Views With Private Saltwater Pool

4.89 out of 5 average rating, 146 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!

Apartment rentals with a pool

A serene view of the ocean at sunset is framed by palm trees. The sky transitions from soft blues to warm tones, while distant boats are visible on the water. Rooftops of nearby buildings add a charming touch to the coastal landscape.

4.93 out of 5 average rating, 155 reviews

RARE FIND - Spacious 2BR, Steps from Ali’i Dr.

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, 227 reviews

Discounted A35 Kona Reef Oceanfront AC Park Free

4.92 out of 5 average rating, 185 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.

Apartment in Kailua

Magic Reef 306 Oceanfront

4.92 out of 5 average rating, 153 reviews

Partial Ocean View, AC, King Bed, 2 Pools

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, 322 reviews

Kailua Village Condo in the Heart of Kona

4.87 out of 5 average rating, 124 reviews

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.

Apartment in Keauhou

Keauhou Garden - Ocean view - Walk to Harbor

A dining table is set with dark dinnerware and glassware, accompanied by a vibrant floral centerpiece. The table is positioned on a balcony with a panoramic view of the ocean and rocky shoreline, where gentle waves can be seen meeting the coast.

4.96 out of 5 average rating, 138 reviews

Lovely 3rd Floor 2 bedroom Ocean Front Condo #312

A spacious lanai offers panoramic ocean views, with wooden furniture arranged for relaxation. A ceiling fan is visible above, and a single palm tree sways gently in the breeze. The ocean's vibrant blue contrasts with the light-colored tiles below.

4.94 out of 5 average rating, 179 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

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, 191 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, 114 reviews

Centrally Located Downtown Kona Condo

5 out of 5 average rating, 45 reviews

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

A cozy indoor hammock is suspended between two points, inviting relaxation. A side table with a small plant adds a touch of greenery. The large sliding glass doors provide a view of the patio and palm trees, allowing natural light to fill the space.

4.91 out of 5 average rating, 103 reviews

Mins to Ocean I By Main Strip I Pool I Hot Tub

A cozy living area features a large window with views of a sunset, showcasing silhouetted palm trees. Two chairs are positioned on a private lanai outside the window, with a minimalist white cabinet and a decorative surfboard accenting the room's decor.

4.96 out of 5 average rating, 134 reviews

Ocean view with central location tropical paradise

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.

4.93 out of 5 average rating, 55 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, 20 reviews

Stunning Oceanfront Beach Condo!