Vacation rentals with a pool in Holualoa

4.88 out of 5 average rating, 297 reviews

A living room area is depicted with a vibrant green sofa, complemented by colorful cushions. Artwork is displayed on the wall above a woven coffee table, while natural light enters through sliding glass doors leading to a balcony. A portable air conditioner is visible in the corner.

Apartment in Kailua-Kona

Ali'i Tiki Hale in the Heart of Kona!

Beautiful 2nd floor condo in cozy 12 unit complex near town. Pool (completely redone in July 2024), BBQ, great location on Ali'i Drive across from Banyans surf beach. 10 minutes drive from Magic Sands, Kahalu'u Beach and Downtown Kona. 1 bdrm, washer/dryer/dishwasher. 2 A/C units, kitchen, bathroom, shower. High speed internet/smart TV. King Bed, sofa bed, snorkel gear. Price includes 17.5% hotel/STVR tax. We have all permits to operate as vacation rental including those required by Bill 108.

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, 194 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!

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, 381 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.

A clear view of the saltwater pool is presented, surrounded by tropical landscaping. Lounge chairs are positioned along the pool's edge, while umbrellas provide shade. The area features a grill and picnic deck, perfect for gatherings.

4.88 out of 5 average rating, 166 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.

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, 155 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!

Guest suite in Kailua-Kona

4.98 out of 5 average rating, 287 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 clear blue pool is surrounded by a light-colored concrete deck, with stainless steel handrails leading into the water. Chaise lounges and a shaded seating area are visible nearby, complemented by tropical landscaping along the fence.

4.93 out of 5 average rating, 120 reviews

Downtown | AC | Pool | Kitchen | Desk |1 Gig | BBQ

º 1 Bed / 1 Bath condo with Pool + Hot Tub, BBQ, A/C, Gig WiFi 6E, Full Kitchen, In-unit Laundry, Patio, pull-out couch + queen air mattress º 5 min walk downtown to restaurants, shops, Ali'i & Kona Pier º Fully stocked and equipped kitchen & bathroom º Desk, chair, 2 monitors, color printer, wired ethernet & Wi-Fi; Full length closet º All beach equipment (chairs, umbrella, towels, snorkels, cooler, body board) º Honda Pilot, Honda HR-V, Honda CR-V or Kia Sportage SX for rent

A cozy studio space is presented with two beds, one a twin covered in a floral quilt and the other a queen with a neutral-toned coverlet. Decorative wall art and a clock adorn the walls, while bedside lamps provide soft illumination. A window offers access to natural light.

4.78 out of 5 average rating, 119 reviews

Condo w/private lanai & a peek-a-view of the pool!

Location! Location! Location! ☀️ Welcome to our centrally located studio condo #318 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!

Guest favorite

A private pool area is showcased, featuring clear blue water and surrounding palm trees. Comfy seating is positioned nearby, along with a grilling station. The sheltered space includes white columns and light-colored tiles, creating a relaxed atmosphere for guests.

Guest suite in Kailua-Kona

4.97 out of 5 average rating, 144 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

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.

A well-maintained pool area is surrounded by tropical landscaping, featuring several lounge chairs and a shaded gazebo. The pool, with clear water, is situated in front of a two-story building, showcasing balconies adorned with decorative railing. Lush greenery frames the scene.

4.8 out of 5 average rating, 171 reviews

Air Conditioned Beach-Front Gem in Kona Town!

Aloha and E Komo Mai! (Welcome) to Kona Escape! This tranquil studio condo with kitchenette is beautifully decorated, clean and located on Ali'i Drive in the Village. It is across the street from Kailua Bay and walking distance to restaurants, shops, churches, Kailua Pier, night life, beaches and ocean activities. There is also a large Farmers Market nearby. We are across the street from IronMan Swim Start/Finish line.