Vacation rentals with a pool in Holualoa

4.99 out of 5 average rating, 308 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, 191 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!

4.96 out of 5 average rating, 130 reviews

Kona Makai Tropical Gdn Oceanfront, OceanVw, Pool

Crashing waves lull you to sleep in our OCEANVIEW Spacious 687sf condo. Steps to the water at the tropical Ocean Front Kona Makai. Our 2nd floor condo sleeps 4 with a King bed in the bedroom + Queen pullout sofabed in the living room. 2 A/C's + fans in each room to keep you cool. W/D in Condo and Full kitchen. Pool & Spa. Beautiful garden view. Gorgeous Oceanview from the Kitchen & Lanai to enjoy the Kona sunset or step down to the lava cliffs for bbq sunset dining! Photos don't do it justice!

4.91 out of 5 average rating, 379 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

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.

4.96 out of 5 average rating, 151 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!

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, 132 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.

4.99 out of 5 average rating, 131 reviews

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.

Home in Kailua-Kona

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.

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, 179 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.

4.96 out of 5 average rating, 157 reviews

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

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.

A view of the ocean is framed by tall palm trees, with a grassy area in the foreground. A road runs parallel to the beach, where pedestrians can be seen walking along the pathway. The sky is partly cloudy, enhancing the coastal scenery.

4.83 out of 5 average rating, 124 reviews

Oceanview condo walking distance to Kona Town

Location! Location! Location! Welcome to our centrally located studio condo #345 in the heart of Kona Town! Nestled between Ali’i Drive and Kuakini Hwy, you’ll be within walking distance of Kona’s best restaurants, shops, beaches, and bars. Enjoy swimming & snorkeling at the nearby pier, just a short walk away. Unwind by the pool or hot tub, take an evening stroll for a nightcap, or start your day with a morning walk for a cup of Kona coffee. Your perfect getaway awaits!

4.89 out of 5 average rating, 111 reviews

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

“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.