Vacation rentals with a pool in Holualoa

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Top-rated rentals with a pool in Holualoa

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Top guest favorite

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.

Condo in Kailua-Kona

4.94 out of 5 average rating, 196 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!

Top guest favorite

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

4.91 out of 5 average rating, 383 reviews

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.

Top guest favorite

The image displays a private pool surrounded by a spacious wooden deck, offering expansive ocean views and lush greenery. Several lounge chairs are positioned near the pool, with a large umbrella providing shade. The bright sky emphasizes the inviting atmosphere.

Guest suite in Kailua-Kona

4.96 out of 5 average rating, 156 reviews

Bungalow Bliss Ocean & Pool View Kailua-Kona HI

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!

Top guest favorite

A clear blue swimming pool is framed by a spacious patio, featuring multiple lounge chairs and a shaded umbrella. Lush tropical plants surround the area, providing a serene backdrop to the private home visible in the distance under a bright blue sky.

Guest suite in Kailua-Kona

4.98 out of 5 average rating, 132 reviews

Welcome to your Hawaiian Getaway

Airport is 20 minutes away. Centrally located to Kailua Kona downtown which has many restaurants and grocery stores. 6 minute drive to White Sands Beach. Fantastic snorkel beach is 10 minutes away. Take a private night dive with the Manta Rays. Walk to Ali’i drive. Travel the island and come back to a relaxing space with a swimming pool. Drive to Hapuna beach and spend the day at a beautiful stretch of white sand along the coast of Kona. Also travel to the waterfalls a must see.

Guest favorite

The living area features a spacious layout with comfortable seating arranged around a central coffee table. Large windows provide expansive views of the ocean and allow natural light to flow in. A dining table is visible in the background, enhancing the shared living space feeling.

Home in Kailua-Kona

4.94 out of 5 average rating, 234 reviews

Epic Kona Views • Pool • A/C • Sleeps 2 Families

Bringing the whole crew—or two families? This breezy 4BR, 3BA Kona home is built for fun and flexibility. Two stories mean plenty of space to gather—or sneak off for quiet time. With two kitchens, two living rooms, A/C, smart TVs, and indoor laundry, everyone gets room to relax. Take in an almost 180° ocean view of Kona bay, lounge on breezy lanais, fire up the BBQ, or float in the pool. Pick fresh mangoes and starfruit on-site. Just 5 mins to Kona town—your perfect island escape awaits.

Guest favorite

Condo in Kailua

4.94 out of 5 average rating, 159 reviews

Renovated 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.

Top guest favorite

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.

Condo in Kailua-Kona

4.97 out of 5 average rating, 188 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.

Top guest favorite

An aerial view of a spacious home surrounded by lush tropical landscaping, showcasing a private pool and hot tub. The colorful gardens feature various plants and trees, with a driveway visible in front of the house, highlighting the serene environment of this one-acre estate.

Home in Kailua-Kona

4.96 out of 5 average rating, 158 reviews

Private Pool - 180° Ocean View - Minutes to Beach

This is real Hawaii (except we have fast reliable Wi Fi). Located at 900 ft. elevation, 4 miles to the center of town where there are many restaurants to choose from and just minutes to the nearest beach where the sea turtles are sunning themselves on the shore. This is on one acre in Kona's safest and most desirable neighborhoods. It is the downstairs of a large home where I live quietly upstairs. You share nothing, the pool and spa are yours exclusively while you are here.

Top guest favorite

Guest suite in Kailua-Kona

4.98 out of 5 average rating, 288 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.

Guest favorite

A private deck surrounds a small swimming pool, framed by lush greenery and colorful foliage. Comfortable seating options, including patterned lounge chairs and a dark wicker stool, are positioned nearby, allowing for relaxation while enjoying views of the ocean in the background.

Guesthouse in Keauhou

4.89 out of 5 average rating, 113 reviews

“Pineapple Cottage” your true Hawaiian getaway

This cozy Holualoa studio offers comfortable accommodations, up-to-date amenities, and a private deck that overlooks the small Kona Coffee farm that resides on the property! While relaxing, relish the lush gardens, sounds of the local wildlife, and ocean views. When you're ready for adventure, head out the door to Kahalua Beach or enjoy a tour of Hula Daddy Kona Coffee. This is the perfect spot for a romantic getaway or a solo trip to the Big Island.

Top guest favorite

The image displays a refreshing saltwater pool, surrounded by tropical plants and equipped with lounge chairs. A barbecue deck and shaded umbrellas are visible nearby, providing an inviting outdoor area. The sleek pool design features a gentle slope, melding with the natural landscape.

Condo in Kailua-Kona

4.96 out of 5 average rating, 265 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!

Guest favorite

An inviting swimming pool is framed by neatly laid concrete and surrounded by lush tropical landscaping. Multiple lounge chairs are positioned beside the pool, with a multi-story condominium visible in the background, showcasing several balconies and greenery.

Apartment in Kailua-Kona

4.95 out of 5 average rating, 266 reviews

KJ's Place, in the heart of the city.

We would like to welcome you to your "home away from home" on the beautiful Big Island! Relax in this stunning, remodeled Kona Ali'i condominium and experience clean, luxurious accomodations in the heart of the city. From here you are within walking distance of all Kona has to offer; from restaurants and shops, to swimming, the Ironman Village (in Oct) & the Christmas Parade (in Dec). We hope you enjoy your stay!