Holiday rentals with a pool in Hawaii

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Top-rated rentals with a pool in Hawaii

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
4.93 out of 5 average rating, 459 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
4.94 out of 5 average rating, 106 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.

Top guest favourite
A charming green cottage is surrounded by lush foliage, featuring a wooden deck with steps leading to the entrance. Large windows reflect the evening light, revealing a cozy interior. Bright blue outdoor chairs are positioned for relaxation amidst the tranquil tropical setting.
Home in Maui
4.97 out of 5 average rating, 246 reviews

Private Hot Tub + Pool Access + AC - Star Lookout

Dreaming of the perfect jungle honeymoon hideaway or retreat? Set amidst a mature coconut grove, (with your own hammock) this private cottage puts you in a romantic world of your own. We have that 'away-from-it-all' feeling but it's only a 20 minute drive to beaches and fabulous restaurants! A perfect romantic hideaway or artist's retreat! ☞ ★Jump Start to The to the Road to Hana! ✔ ☞ ★NEW COLD CENTRAL AC ✔ ★Private Hot Tub ✔ ★Swimming Pool ✔ ★King Bed ✔ ★Sunrise View ✔ ★Outdoor Shower ✔

Top guest favourite
An open-concept living area features a spacious blue sectional sofa and a dining table with wicker chairs. Large sliding glass doors frame ocean views, while vaulted wooden ceilings enhance the airy ambiance. A TV is mounted on the wall, complementing the contemporary decor.
Home in Kapaʻa
5 out of 5 average rating, 153 reviews

Panoramic luxury beachside condo in paradise A/C

Oceanside Paradise. 180 degree Ocean views. Large private Lanai with breathtaking 180 degree views inside and out. See dolphins, whales, turtles, rainbows & amazing sunrises. Steps from beach & centrally located on the famous Coconut Coast & steps from the Lae Nani beach. Beach chairs & gear included. Beautifully remodeled with an open, custom kitchen/baths & vaulted ceiling. Boasts double master suites, Beautiful Pool, BBQ area, beach access, A/C, washer/dryer & private covered parking.

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, 103 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.

Guest favourite
A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.
Apartment in Waianae
4.97 out of 5 average rating, 303 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

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, 160 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, 256 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 favourite
An aerial view showcases a charming cottage surrounded by lush tropical foliage. A private hot tub is nestled on a deck, complemented by a cozy lounging area. Vibrant flowers and greenery create a serene outdoor space, enhancing the sense of seclusion and tranquility.
Cottage in Hanalei
4.95 out of 5 average rating, 370 reviews

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a secluded romantic haven nestled on an acre of lush gardens in Kauai’s breathtaking Wainiha River Valley. Perched on a bluff with panoramic valley views, this retreat offers tranquility and luxury. Unwind by your private pool and spa, surrounded by vibrant tropical flora, where nature creates an atmosphere of enchantment. Just a short drive away, explore some of the world’s most stunning beaches. Let this serene paradise immerse you in romance and blissful relaxation

Guest favourite
A private balcony features a small round table adorned with a colorful mosaic design and two wicker chairs. The view showcases the scenic Waikiki Beach, the shimmering ocean waves, and the lush lagoon bordered by palm trees.
Apartment in Honolulu
4.9 out of 5 average rating, 197 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Top guest favourite
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.
Guest house in Pāhoa
5 out of 5 average rating, 149 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.

Guest favourite
Home in Kihei
4.96 out of 5 average rating, 442 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

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