Vacation rentals with a pool in Holualoa

4.94 out of 5 average rating, 202 reviews

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

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!

4.92 out of 5 average rating, 389 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 pool is featured, surrounded by tropical plants and vibrant flowers. A waterfall flows over black rocks into the clear blue water, providing a serene atmosphere. Sunlight reflects off the water's surface, enhancing the inviting feel of this outdoor space.

4.95 out of 5 average rating, 122 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.

Guest suite in Kailua-Kona

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.

4.99 out of 5 average rating, 135 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.

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.

4.94 out of 5 average rating, 238 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.

4.95 out of 5 average rating, 139 reviews

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.

Condo in Kailua-Kona

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 swimming pool is situated in the foreground, surrounded by tropical foliage. Lounge chairs are positioned poolside, and the two-story house features large windows that invite natural light. The roofline exhibits a distinctive architectural style, contributing to the overall island ambiance.

4.99 out of 5 average rating, 145 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai and Balinese architecture, and ornate, hand-carved wood. Floor-to-ceiling windows and skylights showcase the beauty of the Big Island. The kitchen and living rooms connect to spacious bedrooms with a covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a cooler breeze than busy downtown while not being far from the action.

Superhost

Condo in Kailua

4.94 out of 5 average rating, 161 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.

4.97 out of 5 average rating, 194 reviews

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

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.

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.

4.96 out of 5 average rating, 161 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.