Holiday rentals with a pool in Kalaoa

4.95 out of 5 average rating, 187 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!

4.91 out of 5 average rating, 415 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.

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, 223 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 living area features a comfortable couch with decorative pillows, a glass coffee table, and a patterned area rug. Light-colored walls are complemented by ocean-themed art. A dining space is visible in the background with a modern table and woven chairs. Natural light fills the room.

4.88 out of 5 average rating, 186 reviews

Incredible Downtown Kona /Renovated/New Dual AC

Enjoy this wonderful getaway condo located in the heart of Kailua-Kona. Just steps from Alii Drive, the ocean, Kailua-Kona Pier, grocery stores, farmers markets, restaurants, and coffee stores. Fully renovated. Brand new dual AC (in both living and bedroom). In-unit washer/dryer. High speed wifi. One assigned parking space. Beach gears (snorkeling gears, beach chairs, boogie boards, and beach towels) are ready for you to use. And enjoy the saltwater pool that comes with a grill/picnic deck.

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, 117 reviews

Discounted KonaReef D33 OceanFront* AC* Park Free*

The Kona Reef is being renovated in 2026. Special construction rate of $295 per night! 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, 239 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.

4.95 out of 5 average rating, 155 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, 114 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.

4.93 out of 5 average rating, 176 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.

Apartment in Kailua

*Oceanfront Penthouse in Kona with AC!*

What better way to enjoy Hawaii than having an unobstructed 180 degree view in an oceanfront penthouse? Watch surfers cutting through the waves, turtles gliding in the shallows or whales spouting (in season) from the privacy of your own lanai. With views from both the living and master bedroom, you can relax your days away from the couch or bed. Imagine waking up to the lull of ocean waves at your feet and enjoying sunset dinners on the water’s edge. Truly paradise on the Big Island.

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, 202 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, 243 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 Kalaoa rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 115 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

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

4.91 out of 5 average rating, 162 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

4.97 out of 5 average rating, 197 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, 253 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.

4.95 out of 5 average rating, 112 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

4.89 out of 5 average rating, 148 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 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, 142 reviews

Oceanfront living - Floor to Ceiling wall of glass

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.

4.95 out of 5 average rating, 146 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 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, 290 reviews

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

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, 328 reviews

Kailua Village Condo in the Heart of Kona

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, 119 reviews

Hawaii Retreat with Beautiful Ocean View and AC

A tropical pool area features an inviting swimming pool surrounded by palm trees and lush greenery. Lounge chairs and umbrellas provide shaded seating options, while the two-story building stands in the background, showcasing a charming design that complements the serene atmosphere.

4.89 out of 5 average rating, 108 reviews

Heart of Kona Studio near beach!

Apartment 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.

4.96 out of 5 average rating, 166 reviews

Honua Studio *Ocean Views on the Golf Course!

Other holiday rentals with a pool

5 out of 5 average rating, 21 reviews

Flat in Kailua-Kona

Kona Condo:AC, Near Beach &Shops

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.

4.95 out of 5 average rating, 21 reviews

Clean Stocked Relaxing Kona Home • AC • Pool • BBQ

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, 27 reviews

Stunning Oceanfront Beach Condo!

5 out of 5 average rating, 36 reviews

Flat 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, 56 reviews

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

5 out of 5 average rating, 45 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 dining area is shown on a balcony, featuring a round fruit platter decorated with bananas, pineapple, and tropical flowers. The backdrop includes a clear view of the ocean, framed by palm trees and coastal buildings under a bright blue sky.

5 out of 5 average rating, 35 reviews

Oceanfront AC Penthouse -few feet to Ocean Waves