Holiday rentals with a pool in Hawaii County

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Top-rated rentals with a pool in Hawaii County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view captures the unique 12-sided home adjacent to a round pool surrounded by tropical landscaping. The pool is adorned with lava rock and colorful plants, while a separate structure, likely for amenities, is visible nearby. Lush greenery enhances the tranquil atmosphere.
Home in Pāhoa
4.94 out of 5 average rating, 469 reviews

Romantic Dodecagon Retreat Near a Black Sand Beach

Feel the tropical vibe as sunlight pours into a fun and unique 12-sided home with a central dome skylight and vaulted ceilings. Casual, stylish furnishings, playful textiles, beautiful Balinese hardwood floors, a well-appointed kitchen and a deep, jetted tub with an oversized rain-showerhead create an inviting interior. Outside is the irresistible allure of your own private pool surrounded by lush greenery made complete with a soothing outdoor shower. Enjoy exotic flowers, fruit trees, native plants, and a beautiful lava-rock wall landscaped to give you complete privacy. Close to Kehena Beach! The unique 12-sided architecture includes high-pitched ceilings, Balinese hardwood floors, interior cedar siding w/ Redwood rafters, four screened doors and several screened windows and two Haiku ceiling fans to offer plenty of air-flow and natural light. A large dome skylight offers views of palm trees during the day and the stars at night. With a beautiful, fully-outfitted kitchen that includes spacious, granite countertops, a six-burner gas stove, oven, large refrigerator and a central island, there is plenty of room to prepare meals and to entertain. The well-appointed furniture includes a comfortable day bed, an over-sized, cozy papasan, a custom, artisanal desk, and an organic latex queen-sized bed with 100% cotton, high-thread count sheets. Pool, outdoor shower, and laundry facilities. Dr. Bronner's Liquid Soap, Shikai Shampoo and Conditioner provided. Indoor jet-tub with oversized, rain-type shower-head. Manager (not on property) is available for assistance nearby. Pool guy comes every four days, Mondays & Thursdays around 3pm to maintain pool (will give advance notice). ‘Mahalo Kai’ is immaculately landscaped and surrounded by coconut, mango, ‘soursop’, avocado, papaya, and banana trees. ‘Kehena’ Beach, located just 2 blocks away, is a beautiful black-sand (clothing-optional) beach and is ideal for sunbathing, exploring, picnics, swimming, and body-surfing. Activities include the fun-filled Wed. Night Market at Uncle Robert’s in Kalapana, nearby Farmer's Markets and driving or biking the gorgeous "Red Road": one of THE most scenic coastal roads in the world! There is an island bus. A rental car is recommended. The pool is a 30-foot (10m) round pool with an average depth of 4 feet (1.3m) and, while temperatures can vary depending on weather, it has an average temperature of 82°F (27.8°C). It is typically warmer in the Summer months and a touch cooler in the Winter months. It is tended every three to four days by our pool caretaker. Sorry, but we do not offer a dishwasher for guest use. Please note that cell phone reception tends to be weak at our home but the WiFi is excellent and there is a landline (you will need a calling card for long distance calls.) Mahalo Kai is just a block from the black sand Kehena Beach and 5 miles from a brand new black sand beach. The natural surroundings feature coconut trees, coffee, tropical fruit, and exotic flowers. Activities include bike trails and a night market.

Top Guest favourite
A vibrant sunset casts rich orange and purple hues across the sky, reflecting on the ocean's surface. Palm trees frame the view, while soft outdoor lighting accentuates the lush landscaping below. The tranquil scene invites relaxation and contemplation.
Condo in Kailua-Kona
4.95 out of 5 average rating, 223 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 favourite
A private lanai is featured with a wooden table and two chairs, overlooking the vibrant blue ocean. Palm trees frame the scene against a clear sky, enhancing the peaceful outdoor setting. Colorful plants in pots add a pop of red to the coastal view.
Condo in Kailua-Kona
4.94 out of 5 average rating, 222 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

Guest favourite
A green cottage is set on a lush landscape, featuring a welcoming deck surrounded by tropical plants. A pathway leads to the entrance, with large windows inviting natural light into the space. The clear blue sky enhances the vibrant setting.
Home in Pāhoa
4.94 out of 5 average rating, 579 reviews

Puna Rainforest Retreat Hotspring: Green Bamboo

In a private retreat, this studio offers an idyllic escape with stunning ocean views. A full kitchen and bathroom with a queen-size bed for couples and additional small bed for a child or a small adult. This space is perfect for a romantic getaway or family vacation. Explore the one mile private rainforest trail, unwind in the pool, or experience the unique steam vent hot tubs. The owner resides on the 20-acre property to address any needs that may arise during your stay. TA-008-365-8240-01

Top Guest favourite
The interior of the octagon-shaped Treehouse features a spacious bed adorned with a decorative throw and pillows. Wood paneling offers a warm ambiance, while natural light filters through skylights and windows. A vintage dresser with a mirror complements the rustic decor.
Farm stay in Papaikou
4.94 out of 5 average rating, 173 reviews

Zen Treehouse Private Retreat & Farm Stay

Retreat to a Zen-like setting in the Trees! BRAND NEW (11/24) KING BED w/ DUAL BEDJET air systems for the most comfortable sleep surrounded by nature. Retreat to a Zen-like setting in the trees, slow down and relax in this beautiful redwood octagon artist studio on a working coffee, vanilla and chocolate farm. Private lanai in the treetops tucked into a tropical rainforest. Watch the stars or stream from bed. Wake to birdsong; de-stress, meditate, read, write, dance, create and breathe!

Top Guest favourite
A cozy suite is visible from the entrance, featuring a comfortable full bed dressed with soft linens. A bedside lamp provides warm light, and decorative plants add a touch of nature. The room is complemented by smooth wood flooring and a decorative area rug.
Guest suite in Kailua-Kona
4.97 out of 5 average rating, 172 reviews

Bungalow Bliss Ocean & Pool View

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 favourite
Condo in Kailua-Kona
4.95 out of 5 average rating, 239 reviews

Oceanfront Gem, Walk to Beach/Town, AC, Elevator

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.

Guest favourite
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
4.95 out of 5 average rating, 153 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.

Guest favourite
A circular pool with crystal-clear water is surrounded by lush greenery, including tall ferns and vibrant tropical plants. Sunlight is reflected on the water's surface, creating a serene atmosphere. A wooden deck provides access to the pool, enhancing the natural setting.
Guesthouse in Keaau
4.96 out of 5 average rating, 268 reviews

Magical Jungle Cabin with Pool

Nestled in a lush guava tree grove, this tropical sanctuary offers the nature sounds of camping with the comforts of a cozy bungalow. Perfect for a couple's getaway, a personal retreat, or a peaceful place to retire to after a full day of exploring. Wake up with an outdoor rainfall shower, soak up the Hawaiian sunshine while you float in the pool, grill locally caught fish in the kitchenette pavilion (hot plate and BBQ), and stargaze some of the darkest night skies. Primary residence.

Top Guest favourite
A vibrant tropical garden surrounds a modern villa, nestled within lush greenery and mature palm trees. A serene pool glimmers in the sunlight, creating a peaceful focal point amidst the rich landscaping. The sky above is bright with scattered clouds, enhancing the tranquil atmosphere.
Apartment in Kailua-Kona
4.96 out of 5 average rating, 114 reviews

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.

Top Guest favourite
Lush greenery frames the scene with tall palms swaying gently by the ocean. In the distance, waves roll onto rocky shores beneath a soft sky, where a faint rainbow arcs gracefully over the shimmering water.
Guesthouse in Hakalau
4.96 out of 5 average rating, 261 reviews

Oceanfront Estate Retreat 1 - Carriage w/ Horses

Experience unmatched luxury in a one-bedroom apartment of a world class, $10+M gated oceanfront estate perched on a dramatic cliff edge with a pool. Wake up to breathtaking sunrises, panoramic ocean views in your spacious apartment that features a private lanai, separate living and sleeping rooms, full kitchen, bathroom with walk-in rainfall shower, bidet, and custom furnishings. This property offers privacy, elegance, and stunning surroundings for singles, couples, or honeymooners.

Guest favourite
A tranquil pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant foliage. Lounge chairs are placed around the pool, where guests are seen enjoying the water and the sunny environment. The two-story building with balconies is visible in the background.
Condo in Kailua-Kona
4.9 out of 5 average rating, 467 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

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