Vacation rentals with a pool in Waikoloa Village

4.99 out of 5 average rating, 279 reviews

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.

A cozy living area is highlighted by a brown wicker sofa and matching chairs. Decorative pillows with marine designs adorn the sofa. A round coffee table with a woven texture is positioned on a wooden floor, while two lamps provide soft lighting. Large windows offer views of the surrounding area.

4.95 out of 5 average rating, 130 reviews

Lush Tropical Oasis at Waikoloa Shores, Big Island

Enjoy your stay at this serene 2nd floor, newly remodeled, 2 bedrooms 2 baths condominium in one of the best location of Waikoloa Beach Resort. * Elegant & comfortable * Large lanai with lounge chairs & dining table * Lush tropical landscaping with ponds & waterfalls * Next to pool, tennis court, BBQ & fitness center * Walk to beach, shops, restaurants, entertainments & Grand Hilton * Fast WiFi. Cable TV. Central A/C. Washer & dryer * Spectrum Cable and Roku streaming TVs * Private Parking spot

Lush green lawn stretches out under clear blue skies, framed by swaying palm trees. In the background, manicured homes line a serene body of water, with hints of distant mountains adding depth to the landscape.

4.95 out of 5 average rating, 155 reviews

Casa Chilin-Waikoloa Beach Resort

Aloha and thank you for considering our home for your visit to the Big Island of Hawaii. Our recently remodeled 2bd/2bath home is walking distance from Shopping (Kings/ Queens Shops), Dining, Entertainment, A’ Bay Beach, Historic Sites. The home is stocked with all your basic necessities. 1 covered parking spot included, steps from home. Great location for couples, groups, families with kids, everyone is welcome! Enjoy the sunset and trade wind breeze from the lanai. Washer and dryer in unit.

Superhost

The resort pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant foliage. Loungers are positioned near the pool, providing a relaxing atmosphere. Soft clouds are visible in the sky, creating a serene outdoor environment.

4.89 out of 5 average rating, 115 reviews

Hawaii Big Island Villa | Waikoloa Beach Resort

Our spacious 3 bedroom, 2 1/2 bath villa is the perfect place to call home as you enjoy the Big Island of Hawaii. Located in the Waikoloa Beach Resort area on the sunny Kohala Coast, you will find yourself perfectly situated within all the conveniences while being in a tranquil and private setting. This beautifully appointed villa offers all the comfort and amenities of resort living. A few minutes drive out or a lovely walk away, you will find cafes, shops & restaurants. Welcome to Paradise!

A clear view of a community pool surrounded by palm trees, with lounge chairs set up on the side. The sun shines brightly on the water, creating a refreshing atmosphere. In the background, a clubhouse structure is visible, enhancing the poolside experience.

4.94 out of 5 average rating, 159 reviews

Corner Lanai·Golf Views·Pool·Top 10% Island

Guest Favorite - Top 10% on the Big Island Wake up to golf course views from your private lanai in this bright, renovated corner-unit condo — best-positioned in Fairway Terrace, flooded with natural light. Modern furnishings, fully stocked kitchen & king bed. A/C or open the windows to catch Waikoloa’s evening breezes. Steps from a resort-style pool, hot tub, and gym. Hapuna Beach and A-Bay are 20 min away — world-class snorkeling, surf, and sunsets. Shopping and dining are minutes away.

Apartment in Waikoloa Village

The exterior of a two-story condo is showcased, featuring a light blue and beige color scheme. Lush green grass surrounds the pathway leading to the entrance, with tropical plants and vibrant flowers adorning the landscape. A peaceful atmosphere is suggested by the trees in the background.

Affordable family condo near Hapuna beach

Recent cancellation: Oct 12 -21, now available at discounted rate. You want an unforgettable Hawaii vacation with family and friends. But you're on a budget—we get it. That's why we've created a clean, modern, and comfortable condo with everything you need for an amazing Hawaii vacation—and more money left to enjoy it. Spend less on your stay and more on beaches, adventures, great food, and making memories. If you need anything, our local co-host, Tracy, lives nearby and is happy to help.

4.98 out of 5 average rating, 120 reviews

The image features a lagoon-style pool surrounded by tropical landscaping. Gentle lights illuminate the water, reflecting the vibrant colors of the sunset. Palm trees are visible in the background, and the ocean horizon adds a serene touch to the scene.

4.95 out of 5 average rating, 124 reviews

Hali‘i Kai Ocean View | 3BR/3BA | Sleeps 8

Spacious 3BR/3BA ocean-view townhome ideal for families and friends, with 2 king bedrooms plus a flexible 3rd bedroom. Open concept greatroom and fully-equipped gourmet kitchen. Enjoy stunning ocean and mountain views while you relax in the most spacious floor plan at Hali’i Kai. Everything during your stay will be managed personally by us…the owners. No management companies, no “we’ll get back to you’s.” Our only goal is to make your Hawaiian holiday as memorable (and easy) as possible!

The Ocean Club grounds are depicted, featuring lush tropical landscaping and a lagoon-style pool surrounded by seating areas. Palm trees sway gently in the breeze, with a sunset sky adding a warm glow. Private cabanas offer shaded relaxation spots near the tranquil waters.

4.94 out of 5 average rating, 166 reviews

Newer Luxury Townhouse - Exceptional Value

Hali'i Kai is the nicest ocean front condo resort property in Waikoloa Beach and arguably along the entire Kohala Coast. The grounds & amenities are very nice and appealing to the most discerning of guests. - Ocean Club with its lagoon style pool - Sand bottom hot tub - Ocean front fitness center - Resort bar & restaurant - Tennis and basketball - Beach toys, umbrellas, chairs - Amazing beaches - 2 Pro golf courses - Outdoor shopping - More than 15 restaurants - Great snorkeling

Superhost

A serene pool area is surrounded by palm trees and landscaped gardens. Lounge chairs are positioned around the pool, inviting relaxation. The buildings in the background provide a resort-style ambiance, enhancing the tranquil setting under a clear blue sky.

4.84 out of 5 average rating, 208 reviews

Bright, airy 2 bed, 2 bath, Q sofabed, near pool!

This condo is located within the Waikoloa Beach Resort Area. It is close to the beach (A-Bay--free parking), petroglyphs, restaurants and shopping (King's Court and Queen's Marketplace). You’ll love it because of the location (a 15 min. drive to world class Hupuna Beach), the ambiance, and the relaxing outdoor Lanai with sofa and chairs. It is steps to 1 of 2 pools on the property. It's a good place for solo adventurers, business travelers, couples and families. TA-090-830-2336-01

The cozy sleeping area features a queen bed dressed in crisp white linens, flanked by two bedside tables with lamps. A decorative throw lies across the bed, and plants add a touch of greenery to the room. Natural light filters through the sliding glass doors.

4.97 out of 5 average rating, 197 reviews

Honua Studio *Ocean Views on the Golf Course!

Unwind at Honua Studio in Waikoloa Village, nestled above the Robert Trent Jones golf course. Our cozy retreat offers air-conditioned comfort for those warm Hawaiian nights and a comfortable queen bed, perfect for a couples retreat. Take in the sweeping views of the ocean, golf course, and, on clear days, the distant allure of Maui. Embrace the easygoing vibe, soak up the beauty, and make memories at your own pace. Ready for a relaxed escape? Book your spot at Honua Studio now.

A spacious living area is furnished with a light beige sofa and a complementary love seat adorned with decorative pillows. A dark wood coffee table sits atop a geometric area rug, surrounded by large windows providing natural light and views of greenery.

4.92 out of 5 average rating, 109 reviews

Ka Hale O Malie

This NEWLY remodeled unit comes with central AC, ocean views, high end furnishings, a well stocked kitchen, comfortable beds, two pull out couches and a bathroom for each bedroom! You’ll basically have 3 master bedrooms for you and your guests. Not to mention the amenities! Large pool, kiddie pool, jacuzzi, a brand new tennis/basketball court, small gym, game room, BBQ area with new Weber grills, putting green, well stocked vending machine, and so much more!

The lanai is furnished with a seating area featuring a wooden table and comfortable chairs. A ceiling fan provides airflow, while palm trees frame the sunset view over the horizon. Soft lighting and a calming ambiance are present, creating an inviting outdoor space.

4.95 out of 5 average rating, 103 reviews

Hale Honu -Turtle House Oceanview Luxury Penthouse

Welcome to Hale Hunu – Penthouse Paradise at Vista Waikoloa! This renovated 3rd-floor suite offers ocean, pool, and mountain views from a tiled wraparound lanai. Just a 7-min walk to A-Bay, shops, dining, and more. Enjoy 2BR/2BA, a full kitchen, washer/dryer, Smart TVs, Wi-Fi, and beach gear. Nestled on lush grounds near Hilton Waikoloa, with scenic walking paths. Peaceful, stylish, and perfect for up to 4 guests. Book now and enjoy your Big Island escape!

Popular amenities for Waikoloa Village rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 118 reviews

A clear blue sky envelops a scenic view of the ocean and distant mountains. The foreground includes a residential area with a house featuring solar panels. Lush greenery and palm trees are visible, enhancing the natural landscape.

Home in Waikoloa Village

Island Views Hale - Panoramic Ocean & Sunset Views

4.94 out of 5 average rating, 260 reviews

A single-level home is framed by lush tropical landscaping and solar panels on the roof. A pathway of stepping stones leads to a welcoming outdoor seating area with chairs. The garden features vibrant plants, and warm light reflects off the home's exterior during sunset.

Home in Waikoloa Village

1+ Acre Private Resort | 4BD + 3BTH | Cinema | Spa

4.97 out of 5 average rating, 219 reviews

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

Halia Hale

5.0 out of 5 average rating, 135 reviews

An inviting outdoor space features a private pool surrounded by lush tropical plants. The soft glow of pool lighting highlights the stone patio, while lounge chairs are positioned for relaxation. Tall palm trees are visible against a colorful evening sky.

Home in Keauhou

Mollie’s Paradise Resort Home & Private Pool

4.88 out of 5 average rating, 132 reviews

A stunning community pool area is surrounded by tropical plants and palm trees. Natural stone features create an inviting space, while the clear water reflects the bright blue sky overhead. The pool's design includes gentle curves and relaxation spots, offering a tranquil atmosphere.

Home in Puako

Mauna Lani Golf Paradise*Beach Cards*Bikes

4.99 out of 5 average rating, 112 reviews

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

4.98 out of 5 average rating, 200 reviews

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]

4.96 out of 5 average rating, 173 reviews

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

Condo rentals with a pool

A scenic view of the heated saltwater infinity pool is presented, surrounded by palm trees and lush greenery. Guests can be seen enjoying the pool area, while a golf course and tranquil water feature are visible in the background under a clear sky.

4.98 out of 5 average rating, 128 reviews

Beautiful Villa ... walk to most everything!

A comfortable living area is furnished with a woven sofa and armchairs, complemented by a glass coffee table. Large sliding doors allow natural light to fill the space, revealing views of the golf course and lush surroundings.

4.98 out of 5 average rating, 108 reviews

Beautifully Remodeled 2 BR 2 BA & Stunning Views

An open living area is displayed, featuring a comfortable sofa and armchair with tropical print. A wooden coffee table is centered in the space. Large windows provide views of the outdoor patio, where a dining set is visible, and natural light fills the room.

4.98 out of 5 average rating, 123 reviews

Fairway Villas F33, Penthouse 2 bedroom & Loft

A serene landscape displays a vibrant sunset with hues of purple and orange reflecting on calm water. Silhouetted palm trees line the shore, and boats can be seen docked in the background, enhancing the tranquil atmosphere.

4.79 out of 5 average rating, 165 reviews

Shores 137 - Large 1 BR, minutes from the beach

A modern living area is featured, with a gray sofa and round coffee table at its center. A large television stands on a wooden console. Soft light enters through sheer curtains, illuminating decorative elements such as a potted plant and wall art.

4.83 out of 5 average rating, 115 reviews

Newly renovated, top floor 2 BR condo w/ pool/spa

A tranquil pool area is surrounded by lush greenery and tropical plants. Sun loungers are positioned on the deck, and gentle waves can be seen in the distance. Bright flowers add a pop of color alongside palm trees swaying under a clear blue sky.

4.88 out of 5 average rating, 112 reviews

You Found It. Kolea's Hidden Gem—Read Our Reviews

A scenic view of the ocean is framed by lush greenery and vibrant tropical plants. The rocky shoreline contrasts with the blue waters and the clear sky above. Palm trees sway gently, enhancing the serene coastal atmosphere.

4.99 out of 5 average rating, 105 reviews

Flawless ocean view stay @ Hali’i Kai at Waikoloa

A spacious living area is furnished with comfortable seating arrangements, featuring two large sofas and a glass coffee table. Natural light filters in through the sliding doors, which offer views of the outside lanai surrounded by lush greenery.

4.94 out of 5 average rating, 184 reviews

Hale Le'ale'a - relaxing fun, perfect to de-stress

Other vacation rentals with a pool

An infinity pool glistens in the sunlight, surrounded by lush tropical landscaping. Steps lead from the pool area to a relaxing hot tub, both offering views of palm trees and the nearby golf course. The serene setting invites restful moments and leisure activities.

4.81 out of 5 average rating, 169 reviews

Waikoloa Beach Fairway Villas

4.98 out of 5 average rating, 123 reviews

Villa in Puako

Beachfront Kolea, Garden Level, BBQ on Lanai

An outdoor dining area is surrounded by lush greenery, featuring a table with a decorative surface and four cushioned chairs. A bottle of champagne and glasses are prepared on the table, set against a backdrop of colorful foliage and a well-maintained garden.

4.98 out of 5 average rating, 156 reviews

Luxurious 3 bedroom at The Fairways at Mauna Lani

A clear pool reflects the blue sky and surrounding palm trees, featuring a gently sloping entry. Covered seating areas are visible nearby, with lounge chairs arranged for relaxation. The scene conveys a serene atmosphere ideal for enjoying the outdoors.

4.94 out of 5 average rating, 204 reviews

Spacious Fairways 2BD townhome. Pool/Beach Club!

4.97 out of 5 average rating, 86 reviews

A spacious home with a modern design features solar panels on the roof, surrounded by lush landscaping. The backyard showcases a large swimming pool and spa, accompanied by chaise lounge seating. Nearby, vibrant tropical flowers enhance the serene outdoor environment.

Home in Puako

Luxury Home w/Pool + Spa | Sleeps 10 | Waikoloa Re

A spacious lounge area is highlighted by a light-colored sectional couch, positioned to offer views through large windows. Natural light fills the space, with a textured area rug beneath a wooden coffee table. Greenery is present, enhancing the connection to the outside landscape.

4.92 out of 5 average rating, 96 reviews

NEW! Expansive OceanView Retreat/Best Beaches/ AC

A spacious living area features soft cream-colored sofas arranged for comfort. Natural light fills the room through large windows, while a warm, woven pendant light hangs above. A wooden side table holds a cup, complementing the relaxed atmosphere.

4.96 out of 5 average rating, 73 reviews

Hilton Pool • Designer Penthouse • Walk2Beach