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

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

🌴 Guest Favorite - Top 10% on the Big Island Enjoy stunning ocean, mountain, sunset, and starry views from nearly every room in this cozy, family-friendly three-bedroom, two-bathroom Waikoloa Village, Hawaii home. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear such as boogie boards, snorkels, coolers, umbrellas, towels and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys, and a BBQ grill.

LocationFamilyAir conditioning

4.99 out of 5 average rating, 282 reviews

Top Guest favourite

The oceanfront lanai features a dining table with four wooden chairs, overlooking a sunset-lit ocean. Two lounge chairs are placed nearby. Palm trees frame the scene, and string lights provide a soft glow, enhancing the serene atmosphere.

Condo in Holualoa

Ocean-front penthouse, sunsets, whales, surfers!

*Gorgeous views from oceanfront lanai *See whales, surfers, turtles from lanai *Beach/snorkel/surf right outside *4th Floor Penthouse w/ A/C *Stocked kitchen incl air fryer *Covered parking *Oceanfront Gas grill *Da Poke Shack in complex *Pack 'N Play/High Chair *Shared Pool w/ hot tub *Completely remodeled w/ split air unit & double vanity in master

FamilyValueWalkability

4.99 out of 5 average rating, 127 reviews

Top Guest favourite

A serene outdoor space features a sparkling turquoise pool and a hot tub, with a stunning sunset in the background. Comfortable seating under an umbrella is arranged nearby, surrounded by lush greenery and palm trees, enhancing the tranquil atmosphere.

Home in Kailua-Kona

Private Pool - 180° Ocean View - Minutes to Beach

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

ValueLocationBackyard

4.96 out of 5 average rating, 174 reviews

Guest favourite

A spacious living area is shown with a light-colored rug and comfortable seating, complemented by ceiling fans. Large glass doors open to an outdoor space, revealing views of the adjacent garden and ocean. Natural light brightens the room, enhancing its airy feel.

Townhouse in Keauhou

Seahorse Luxury Suite at Seaspray Ocean View

A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a great place to relax with ocean views and the sounds of ocean waves. The chef of the family will appreciate a fully stocked modern kitchen. The whole group will enjoy everything Kona has to offer from this centrally located Oasis.

ValueLocationDecor

4.92 out of 5 average rating, 131 reviews

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.

FamilyValueCheck-in

4.95 out of 5 average rating, 118 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

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

LocationFamilyCheck-in

4.99 out of 5 average rating, 113 reviews

Top Guest favourite

Condo in Kailua-Kona

True Oceanfront, Top-Floor, Downtown, A/C, Parking

Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

ValueLocationNearby

4.94 out of 5 average rating, 208 reviews

Top Guest favourite

Home in Holualoa

Kona Estate: Infinity Pool, Ocean Views, Orchard

Welcome to Akoa Hale — wake up to sweeping 180° Pacific Ocean views and step outside to your private 40-ft heated saltwater infinity pool and spa. Beyond it, over 1 acre of lush tropical orchard — fresh mango, citrus, and starfruit all yours to pick. The covered lanai. The deep, rare quiet of an exclusive gated Kona estate for up to 10 guests. And yet, Magic Sands Beach, Ironman Pier, and the best restaurants on Ali'i Drive, all just minutes away. This is Hawaii living at its absolute finest.

FamilyValueAmenities

4.96 out of 5 average rating, 129 reviews

Top Guest favourite

A tranquil pool area features a heated pool with a small waterfall and tropical landscaping. Two lounge chairs sit beside the pool, adorned with rolled towels and a refreshing drink. The vibrant greenery enhances the serene atmosphere.

Home in Holualoa

Tropical oasis: Heated pool, hot tub & ocean views

Immaculate updated home nestled on a private corner lot in an upscale gated community, just minutes away from downtown Kona. Immerse yourself in the resort-style backyard w/a heated pool, a cascading waterfall, a relaxing hot tub and lush tropical landscaping. Comfortably sleeps 8, perfect for families. Enjoy fast Wi-Fi, smart TVs, luxurious linens, updated bathrooms, a well-stocked kitchen, and plenty of beach and pool gear to make your stay truly memorable. Fully licensed: STVR-19-365351

FamilyValueLong stay

4.99 out of 5 average rating, 156 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.

LocationValueCheck-in

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

LocationFamilyNearby

4.94 out of 5 average rating, 136 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

Relax and enjoy 3.5 acres of tropical paradise with epic ocean views, complete privacy, and pure natural surroundings. You'll be far from traffic, crowds, and noise. Just sunsets and total relaxation enjoyed from the spacious lanais, pool deck, or hot tub. The views and setting are unmatched. This is a peaceful, rural retreat away from commercial areas. The distance from town is intentional and is ideal for guests who value tranquility and space over convenience.

ValueFamilyAir conditioning

4.99 out of 5 average rating, 100 reviews