Vacation rentals with a pool in Kailua-Kona

A serene swimming pool is surrounded by lush tropical landscaping and palm trees. Several lounge chairs and shaded umbrellas are arranged around the pool area, inviting relaxation under the clear blue sky. The sun casts a warm glow, illuminating the vibrant greenery.

4.99 out of 5 average rating, 337 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

4.94 out of 5 average rating, 102 reviews

A spacious saltwater pool is framed by a wide deck featuring a circular seating area. The modern villa above offers multiple glass doors, providing easy access to outdoor views and relaxation spaces. Lush greenery and a clear blue sky enhance the serene atmosphere.

Home in Kailua-Kona

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.

An aerial view of the Sea Village complex highlights the oceanfront pool and spa area. Surrounding lush greenery and well-maintained gardens enhance the inviting atmosphere. Umbrellas shade the lounge chairs placed around the irregularly shaped pool, while the communal BBQ area is positioned nearby.

4.94 out of 5 average rating, 206 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!

An oceanfront view features a serene swimming pool, surrounded by palm trees. The calm waves of the Pacific Ocean are visible in the background, reflecting the sunlight. The landscape includes a rocky shoreline, enhancing the coastal atmosphere.

4.93 out of 5 average rating, 211 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

4.99 out of 5 average rating, 100 reviews

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.

Home in Kailua-Kona

Exceptional Oceanview Home - Pool & Stunning View

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

A refreshing pool is situated beside the ocean, surrounded by a patio area with lounge chairs. The backdrop features a multi-story building with balconies and palm trees, contributing to a relaxed coastal atmosphere under a clear blue sky.

4.93 out of 5 average rating, 162 reviews

True Oceanfront, Top-Floor, Downtown, A/C, Parking

Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

An oceanfront condo complex is shown, featuring a heated saltwater pool surrounded by lounge chairs. The building's balconies overlook the ocean, with a rocky shoreline visible. Clear blue skies enhance the tranquil setting, emphasizing the proximity to the water.

4.97 out of 5 average rating, 226 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, 140 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, 100 reviews

A tranquil backyard scene features a clear blue pool surrounded by mature tropical landscaping. The two-story villa is partially visible, showcasing large windows and a well-maintained exterior. Sunlight brightens the area, creating a relaxing 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.

4.97 out of 5 average rating, 202 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

4.98 out of 5 average rating, 301 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 tranquil swimming pool is surrounded by a stone patio and lounge chairs, offering ocean views. Palm trees gently sway in the background under a clear blue sky, creating a peaceful atmosphere for relaxation and enjoyment.