Holiday rentals with a pool in Kalaoa

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

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

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!

4.91 out of 5 average rating, 407 reviews

A sparkling swimming pool is surrounded by tropical plants, lounge chairs, and shaded umbrellas. The inviting water reflects the vibrant greenery and the house sits gracefully in the background, framed by palm trees and a clear blue sky.

Guest suite in Holualoa

Cozy Couples Retreat- Guest Suite w/ Pool & Patio

Perched above Kona on a serene hillside, the Monkeypod Villa offers a peaceful escape on a private country estate. Nestled off the beaten path & away from tourist crowds, you're just a scenic 7-mile drive from downtown Kona and pristine beaches. Wake to the gentle chorus of birds and sip your morning coffee beneath the shade of a magnificent monkey pod tree. After a day of exploring the Big Island, take a refreshing dip in the pool & unwind as the sky transforms with a stunning Hawaiian sunset.

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!

A table set for two features a bottle of wine, glasses, and a vibrant fruit arrangement, including pineapples and flowers. The backdrop consists of stunning ocean views and rocky shoreline, viewed from the condo's lanai.

4.97 out of 5 average rating, 234 reviews

Right-on-Ocean; Renovated; Walk to Beach/Town, A/C

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.

4.95 out of 5 average rating, 150 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, 109 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.

Flat 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, 211 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 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.

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, 234 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!

Popular amenities for Kalaoa rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 113 reviews

A clear blue sky envelops a scenic view of the ocean and distant mountains. The foreground includes a residential area with a house featuring solar panels. Lush greenery and palm trees are visible, enhancing the natural landscape.

Home in Waikoloa Village

Island Views Hale

A serene outdoor space features a private heated pool surrounded by tropical plants. Comfortable seating with umbrellas offers shade and relaxation. Ocean views are visible in the background, enhancing the tranquil atmosphere of the garden area.

4.99 out of 5 average rating, 80 reviews

Kini Kini Pua – Private Retreat in Paradise!

4.96 out of 5 average rating, 110 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

4.94 out of 5 average rating, 247 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, 18 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, 242 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

Apartment rentals with a pool

4.92 out of 5 average rating, 152 reviews

Partial Ocean View, AC, King Bed, 2 Pools

Apartment 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.

4.94 out of 5 average rating, 139 reviews

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

Superhost

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, 320 reviews

Kailua Village Condo in the Heart of Kona

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, 222 reviews

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

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, 178 reviews

2 Bedroom Penthouse Condo With Ocean View And Pool

A sandy beach area is surrounded by palm trees and lounge chairs, offering a serene seaside escape. Tiki torches stand along the pathway, and colorful flowers add to the landscape, while a soft sunset glow reflects on the ocean.

4.87 out of 5 average rating, 325 reviews

O/F View, on ocean 1 Bdrm, Casa De Emdeko Ironman

4.98 out of 5 average rating, 101 reviews

The upper left image showcases a private lanai with outdoor seating and an umbrella, framed by lush greenery and a sunset view. The upper right captures a well-lit king bedroom featuring soft bedding and tropical decor. The lower left displays an inviting open-concept living area with bright decor and cozy seating. The lower right reveals a scenic ocean view, surrounded by verdant foliage.

Apartment in Keauhou

Kona Ocean-View Retreat w/ A/C & Private Lanais

A well-maintained saltwater pool is surrounded by lush Hawaiian greenery and palm trees. Lounge chairs are positioned around the pool area on a stone patio, offering ample space for relaxation. Umbrellas provide shade for guests enjoying the outdoor amenities.

4.92 out of 5 average rating, 295 reviews

Kalanikai Condos! 5 Min walk to Kona Pier!

Other holiday rentals with a pool

5 out of 5 average rating, 36 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.

Flat in Kailua-Kona

Gorgeous Unit, Stunning Views!

4.96 out of 5 average rating, 113 reviews

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.

Flat in Kailua-Kona

Centrally Located Downtown Kona Condo

5 out of 5 average rating, 23 reviews

A rustic cabin is framed by lush trees and vibrant greenery. The entrance features a wooden deck with a railing. Large glass sliding doors provide a view into the interior, while natural landscaping enhances the inviting presence of the space.

Cabin in Kealakekua

Cozy jungle 2-bedroom cabin (TA-154-746-2656-01)

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, 53 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!

5 out of 5 average rating, 33 reviews

Flat in Keauhou

NEW! ADORABLEbungalow in Kona

5 out of 5 average rating, 39 reviews

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.

Apartment in Keauhou

Brand new Luxury Oceanfront Living in Kona with AC

A modern kitchen sink is situated beneath large windows, offering views of palm trees and the ocean. The contrasting dark cabinetry and light marble countertops are complemented by decorative plants on the windowsill, creating an inviting cooking space.