Vacation rentals with a pool in Island of Hawai'i

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Top-rated rentals with a pool in Island of Hawai'i

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

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Top guest favorite
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.

Guest favorite
An expansive saltwater pool is framed by a wooden deck, offering views of the ocean and colorful sunset skies. Tropical foliage partially obscures the scene, adding a serene touch. The tranquil surroundings invite relaxation and peaceful moments.
Home in Kailua-Kona
4.95 out of 5 average rating, 111 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments of your life unfold. Tranquility, privacy, and stunning beauty await you. A masterclass of design in harmony with nature, this exquisite and inspired home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light.

Guest favorite
The modern villa features a large swimming pool reflecting the clear blue sky. A spacious outdoor area is bordered by tropical landscaping, with a combination of floor-to-ceiling glass walls and classic modernist design elements visible in the structure.
Villa in Pāhoa
4.94 out of 5 average rating, 106 reviews

Lava Flow House Pool Ocean View Kehena Beach w A/C

This luxurious modernist masterpiece with swimming pool and ocean view, sits in a serene setting in the untouched area of the Puna Coast on the Big Island of Hawaii. If you love great design and style, fantastic tropical weather, rugged yet lush landscapes, blue ocean, and relaxation, then you will love this place for your next vacation. The unique combination is a stunning contrast of rugged landscape and sharp minimalist architecture. This is a shared family home with a Main house and Studio.

Top guest favorite
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, 221 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

Top guest favorite
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
4.95 out of 5 average rating, 172 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 favorite
A private solar heated pool is surrounded by tropical landscaping, featuring a waterfall cascading over black rocks. Comfortable outdoor seating is arranged nearby, with vibrant plants adding color and lushness to the serene atmosphere.
Home in Kailua-Kona
4.96 out of 5 average rating, 136 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 favorite
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, 267 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 favorite
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, 260 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.

Top guest favorite
Home in Kailua-Kona
4.98 out of 5 average rating, 155 reviews

Peaceful Paradise

Experience ALOHA in this spacious, ocean view gem!💎 2 miles to downtown Kona. Comfortable, clean, sun-kissed and welcoming. Perfect for unwinding after a day of island sight-seeing. The charming, stylish space has a private entrance and is located on the ground floor of a large two-story home. You will experience all the comforts of home including an ohana kitchen, living area, bbq, and lovely, large outdoor lanai. Our goal is to give 5 star stays to every guest!

Superhost
An aerial view displays the cedar home nestled in lush greenery, with a pool and the ocean visible in the background. The surrounding landscape features hills and diverse vegetation, creating a serene atmosphere, with clear skies enhancing the scene.
Home in Papaaloa
4.85 out of 5 average rating, 114 reviews

Lush Paradise—Luxury Eco-Getaway

Escape to our luxurious cedar home on Hawaii's main island. Surrounded by rainforest, waterfalls, and a stream, our sustainable retreat offers serenity just 25 mins from Hilo. With 4 beds, 2 baths, and an open-concept kitchen, our spacious home blends Hawaiian charm with modern amenities. Unwind on the travertine lanai, and explore fruit trees and trails. Perfectly located for beach adventures and vibrant towns. Experience tropical living at its finest. Book now!

Top guest favorite
An outdoor spa room is shown, featuring a freestanding soaking tub that overlooks lush greenery. A comfortable day bed with a striped blanket is positioned nearby. Shelves display various spa products, while natural light filters in through large windows.
Guesthouse in Pāhoa
5 out of 5 average rating, 154 reviews

Kehena Beach Loft

Rural Beautiful space across street from serene black sand beach. One hour from Volcano National Park. Take it easy at this unique and tranquil getaway. Kehena Beach loft is part of an one acre luxury estate. You will have your own private separate corner of property, you wont see another person. We are remote, tranquil, one with nature. A great place to unplug, listen and watch ocean waves come ashore. Near several local markets , black sand beach.

Top guest favorite
A large lap pool is surrounded by a wooden deck and tropical landscaping. Poolside loungers are positioned for relaxation, with views of the ocean and distant trees. The area is bathed in natural light, creating a serene outdoor atmosphere.
Home in Kailua-Kona
4.97 out of 5 average rating, 201 reviews

Halia Hale

Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

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