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Holiday 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 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, 463 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 favourite
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, 110 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 favourite
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, 105 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 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.
Apartment in Kailua-Kona
4.94 out of 5 average rating, 220 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 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
4.95 out of 5 average rating, 169 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!

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.
Apartment in Kailua-Kona
4.95 out of 5 average rating, 151 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.

Top guest favourite
The spacious home features natural wood accents, a wide balcony, and large windows that reflect the tropical landscape. Surrounding gardens with lush greenery create a serene atmosphere, while a small pond with a waterfall adds a soothing element to the exterior.
Home in Kailua-Kona
4.99 out of 5 average rating, 165 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.

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.
Guest house in Hakalau
4.96 out of 5 average rating, 258 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.

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, 111 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 favourite
An open-air spa room features a soaking tub positioned on a wooden deck, surrounded by greenery. Two lounge chairs are placed nearby, inviting relaxation. The horizon is visible, hinting at a serene sunset, with soft colors illuminating the evening sky.
Guest house in Pāhoa
5 out of 5 average rating, 151 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 favourite
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, 200 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.

Top guest favourite
A spacious interior showcases a king bed with soft linens, positioned to offer views of the ocean through large sliding glass doors. A dining area with bar stools overlooks the water, while light drapes frame the windows, enhancing the coastal ambiance.
Apartment in Kailua-Kona
4.98 out of 5 average rating, 170 reviews

NEW! UNIQUE Top floor Oceanfront Magic Sands Beach

Aloha! Location, Location, Location! + NEWLY Remodelled interior & has A/C! This unique oceanfront is located on the TOP floor of Kona Magic Sands condominiums. It features A/C, brand NEW stainless steel appliances (Full kitchen & Dish Washer). The honest, elegant and minimal interior design of this space quietly invites in the majestic Pacific Ocean and its breathtaking sunset views. THE VIEW! THE DESIGN!

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