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Holiday rentals with a pool in Hawaiian Islands

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Top-rated rentals with a pool in Hawaiian Islands

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

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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 Puna

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.

4.95 out of 5 average rating, 118 reviews
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 Wailua

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.

5.0 out of 5 average rating, 189 reviews
Guest favourite
A large oceanfront pool area is surrounded by lush tropical landscaping and swaying palm trees. The inviting pool features a gradual entry and a spacious deck for relaxation, with the ocean visible in the background under a clear blue sky.
Cottage in Molokai

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore, or unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

4.95 out of 5 average rating, 128 reviews
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 Makaha

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.

4.97 out of 5 average rating, 344 reviews
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 Holualoa

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai/Balinese architecture, hand-carved wood everywhere, and ample windows/skylights that showcase the beauty of the Big Island. The kitchen/living rooms connect to the owner's retreat via covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a quiet atmosphere and cooler temps than busy downtown while not being far from the action.

4.98 out of 5 average rating, 202 reviews
Guest favourite
Home in Holualoa

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 unfold. Tranquility, privacy, and beauty await you. A masterclass of design in harmony with nature, this exquisite 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. Tax ID # TA-110-823-1680-01

4.94 out of 5 average rating, 136 reviews
Guest favourite
A spacious living area features a king size bed with fresh linens, complemented by two boucle fabric chairs and a round coffee table. Natural light filters through a nearby window, highlighting the modern wood accent wall and a decorative wall clock.
Flat in Waikiki

39FL-Chic Modern in Waikiki-Upgraded King Studio

With high-end finishes and a newly renovated interior, this studio in Waikiki is picture-perfect. Located on the 39th floor, it boasts partial ocean views and views of the Waikiki skyline. The building is surrounded by amazing dining and shopping options. The world-famous Waikiki beach is only a few minutes' walk away. Whether you're traveling as a couple or a small family, this unique experience is perfect for you. You'll feel right at home with all the essential amenities provided.

4.95 out of 5 average rating, 138 reviews
Top guest favourite
A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.
Flat in Napili-Honokowai

Maui Full Oceanfront Paradise

Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

4.97 out of 5 average rating, 107 reviews
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

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

4.95 out of 5 average rating, 406 reviews
Top guest favourite
A serene sunset view is captured over the ocean, with silhouettes of trees and palms framing the scene. The sky displays soft hues of orange and pink, reflected gently on the water's surface. The tranquil atmosphere is complemented by a still pool in the foreground.
Guest house in Hakalau

Oceanfront Estate Retreat 2 - Solar w/ Horses

Experience unmatched luxury in a private, hi-end artistic apartment on 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 this spacious apartment featuring living, dining, desk, garden, sleeping, kitchen, bathroom with walk-in rainfall shower, bidet, and a luxurious furnishing. This property offers privacy, elegance, and stunning surroundings for singles, couples, or honeymooners.

4.93 out of 5 average rating, 277 reviews
Guest favourite
A spacious bedroom is illuminated with natural light, featuring a large bed adorned with a patterned blanket. A wall decorated with palm leaf designs complements the beach view visible through expansive glass doors, which open onto a private balcony with an outdoor seating area.
Apartment in Waikiki

Floor-to-Ceiling Oceanfront Home (Car Available)

* Aloha! Welcome to the happiest place in the world. * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. This beachfront home is within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Every time I come to Hawaii, I am so happy. I hope our place can bring you some happiness too. :-)

4.93 out of 5 average rating, 130 reviews
Top guest favourite
An inviting interior is captured from an elevated perspective, featuring a spacious bed with white linens and blue accent pillows. Warm wood floors enhance the cozy ambiance, while large windows frame outdoor views. A dining area with chairs is visible through the glass doors, complemented by soft lighting.
Apartment in Maunaloa

Sweet Upstairs Corner Ocean View Studio on Molokai

Top floor corner unit at Kepuhi Beach Resort, on the special island of Molokai....in between Maui and Oahu! Vaulted open ceilings, spacious and airy. Completely remodeled and freshly outfitted. Close to beach and ocean-side pool, views of Kaiaka Rock, ocean surf, vivid sunsets. Fully equipped kitchen, luxurious King sized bed. Fast wireless , 40” SmartTV. Perfect setting to unplug, hike or bike the red dirt trails, explore beaches, and experience Molokai fully.

4.97 out of 5 average rating, 270 reviews

Popular amenities for Hawaiian Islands rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
A panoramic view of the ocean stretches across the horizon, framed by scattered clouds in a clear blue sky. Lush greenery and rooftops are visible in the foreground, with tall trees adding height to the landscape, creating a serene scene.
Home in Waikoloa Village

Ocean, Sunset, Mountain & Celestial Views

4.99 out of 5 average rating, 282 reviews
Top 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 Puna

Puna Rainforest Retreat Hotspring: Green Bamboo

4.94 out of 5 average rating, 613 reviews
Top guest favourite
A tranquil scene features lush greenery and palm trees framing a scenic view overlooking a valley. In the distance, mountains are visible against a colorful sunset sky, with soft clouds adding depth to the picturesque landscape.
Home in Makawao

Exceptional Upcountry Villa, breathtaking views!

4.94 out of 5 average rating, 108 reviews
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 County

Private Hot Tub + Pool Access + AC - Star Lookout

4.97 out of 5 average rating, 275 reviews
Top guest favourite
The image captures a panoramic view of a private heated swimming pool surrounded by lush greenery. Lounge chairs are positioned around the pool, and a shaded gazebo adds to the outdoor space. In the background, the vibrant blue ocean stretches under a clear sky.
Home in Holualoa

Exceptional Oceanview Home - Pool & Stunning View

4.99 out of 5 average rating, 113 reviews
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 Puna

Romantic Dodecagon Retreat Near a Black Sand Beach

4.93 out of 5 average rating, 507 reviews
Top guest favourite
An outdoor lanai features comfortable seating with a coffee table, overlooking vibrant tropical foliage and ocean views. The wooden deck reflects warm tones, while the ceiling showcases exposed beams. An American flag is visible to the side, and a hot tub is positioned nearby, awaiting relaxation.
Home in Captain Cook

Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Views

4.99 out of 5 average rating, 100 reviews
Top guest favourite
Home in Princeville

Princeville Home w/Private Pool and Mountain View

4.96 out of 5 average rating, 173 reviews

Apartment rentals with a pool

Top guest favourite
Apartment in Napili-Honokowai

On Top of Water View-5 Stars-Pohailani 303

4.98 out of 5 average rating, 252 reviews
Guest favourite
A corner studio offers large windows with panoramic views of the city and mountains, allowing natural light to fill the space. A spacious bed is positioned near the window, complemented by a modern desk area with stylish chairs. Soft blue curtains frame the windows.
Apartment in Waikiki

Renovated Cozy Home in Waikiki

4.89 out of 5 average rating, 381 reviews
Top guest favourite
A serene pool area is surrounded by lush tropical foliage. The water is clear, reflecting the natural surroundings, with a thatched-roof cabana visible in the background offering shaded seating. The name 'Bamboo' is subtly integrated into the pool's design.
Apartment in Waikiki

Large Corner Unit at Bamboo with Full Kitchen

4.8 out of 5 average rating, 392 reviews
Guest favourite
Apartment in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

4.94 out of 5 average rating, 149 reviews
Top guest favourite
An inviting lanai features a woven hanging chair beside a small round table. A steaming cup is placed on the table, accompanied by a book. The background reveals lush greenery and panoramic ocean views under a soft sunset glow.
Apartment in Princeville

~The Surfshack~ with breathtaking ocean views!!

4.99 out of 5 average rating, 366 reviews
Top guest favourite
A tranquil outdoor seating area features a cozy hanging chair beside a round dining table. The expansive balcony overlooks city views and distant mountains, with soft clouds enhancing the bright sky. Green plants add a touch of nature to the serene space.
Apartment in Waikiki

38th FLR- Luxury King Boutique Studio 1000 Cranes

4.95 out of 5 average rating, 175 reviews
Guest favourite
A cozy seating area is highlighted by a green sofa adorned with a decorative pillow featuring a flowered design. A small side table with a potted plant is positioned nearby, and wall art displaying a tropical motif adds visual interest to the space.
Apartment in Waikiki

Fall Promos! 1.5 Blocks to the beach Pool+hot tub

4.91 out of 5 average rating, 214 reviews
Top guest favourite
A spacious King Size Bed is presented with plush pillows, complemented by a bedside lamp. The large sliding glass doors provide access to a private balcony featuring outdoor seating. A vibrant landscape photo adorns the wall above the bed, enhancing the modern decor.
Apartment in Lahaina

Lahaina Studio: Beachfront, Mountain View, Hot Tub

4.95 out of 5 average rating, 303 reviews

Other holiday rentals with a pool

Superhost
A spacious studio features a king size bed with a plush mattress, flanked by bedside lamps. A large window allows natural light to fill the room, complemented by soft neutral tones. A 75-inch smart TV is mounted on the wall, and a wooden table with water bottles and amenities is in the foreground.
Flat in Waikiki

Walk to the beach!-Cozy Renovated Waikiki Studio~

4.89 out of 5 average rating, 120 reviews
Guest favourite
A spacious studio is highlighted by a large 65” Smart TV and a king-size bed featuring fresh linens. Natural light pours in from the sliding glass doors, leading to a balcony. A dedicated work area with a desk and chair complements the modern decor.
Apartment in Waikiki

43F-Island Colony Studio-Ocean & City Skyline View

4.95 out of 5 average rating, 151 reviews
Top guest favourite
A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Apartment in Maalaea

Coastal Dream Oceanfront Condo!

4.98 out of 5 average rating, 127 reviews
Top guest favourite
A modern studio space features a queen-sized bed with a soft aqua throw. Light wood accents and a wooden feature wall complement the decor. An open kitchen area is equipped with appliances, including a blue stove, while a small dining table with two stools is visible nearby.
Flat in Waikiki

Luxury Waikiki Condo w/ Retro Charm & FREE Parking

4.98 out of 5 average rating, 116 reviews
Guest favourite
A spacious living area showcases a king-size bed with fresh linens and a plush mattress. Natural light floods the room through large glass windows, complemented by a cozy seating area featuring a table and two chairs, and a sleek entertainment unit housing a large flat-screen TV.
Flat in Waikiki

43FL-Modern High-FL Studio w/Ocean & City Views

4.95 out of 5 average rating, 115 reviews
Guest favourite
A modern bedroom features a spacious white bed with neatly arranged linens and a soft blue throw. A mirrored closet reflects the room’s layout. The kitchen area, equipped with appliances, is visible in the background, enhancing the open and airy feel of the space.
Flat in Waikiki

Ocean View Corner Modern Studio w/ Full Kitchen

4.91 out of 5 average rating, 219 reviews
Top guest favourite
Two sparkling glasses of rosé wine are positioned beside a bottle on a tiled table. Softly flickering candles are set within arm's reach, while a scenic sunset casts warm hues across the sky, viewed through an open balcony overlooking the ocean.
Apartment in Maunaloa

Oceanfront Condo With Glorious Ocean View

5.0 out of 5 average rating, 71 reviews
Top guest favourite
Lush green lawns are framed by swaying palm trees, leading to a serene ocean view in the distance. The sky is bright and partly cloudy, enhancing the tranquil atmosphere of the surrounding landscape.
Apartment in Maunaloa

2BR Home, Amazing Views, Pool, Lanai, Fast WiFi

4.98 out of 5 average rating, 55 reviews

Destinations to explore