Holiday rentals with a pool in Waikoloa Village

4.99 out of 5 average rating, 271 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.

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, 151 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.

4.9 out of 5 average rating, 113 reviews

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.

Townhouse in Puako

Hawaii Big Island Waikoloa Beach Luxury Villa

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!

Apartment in Waikoloa Village

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, 156 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.

4.97 out of 5 average rating, 191 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]

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.

4.93 out of 5 average rating, 273 reviews

Home in Holualoa

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

Bringing the whole crew—or two families? This breezy 4BR, 3BA Kona home is built for fun and flexibility. Two stories mean plenty of space to gather—or sneak off for quiet time. With two kitchens, two living rooms, A/C, smart TVs, and indoor laundry, everyone gets room to relax. Take in an almost 180° ocean view of Kona bay, lounge on breezy lanais, fire up the BBQ, or float in the pool. Pick fresh mangoes and starfruit on-site. Just 5 mins to Kona town—your perfect island escape awaits.

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.

4.99 out of 5 average rating, 121 reviews

Beautiful Villa ... walk to most everything!

Location, Location, Location! Fairway Villas is walking distance to most everything you could want. Located in beautiful Waikoloa, this condo is arguably the best unit in the entire complex. You have beautiful views of Mauna Kea, the heated saltwater infinity pool, the golf course and palm trees. Walk to A-Bay Beach & the grocery store, most restaurants are a short walk, Tommy Bahamas Restaurant, Lava Lava Restaurant, Starbucks, the Hilton Waikoloa Village. Must be 25 years old to book.

Apartment in Waikoloa Village

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, 188 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 comfortable living area features a beige sofa, complemented by colorful cushions. A wooden coffee table sits at the center, with a decorative bowl on top. In the background, a modern kitchen and dining space are visible, creating an open and inviting layout.

4.96 out of 5 average rating, 165 reviews

Enjoy lush tropical lifestyle in Waikoloa Resort

Enjoy your stay at this serene ground floor, remodeled in 2023, 1 bedroom 1 bath corner unit condominium in one of the best location of Waikoloa Beach Resort. * Lush tropical landscaping with ponds and waterfalls * Next to pool, tennis court, BBQ and fitness center * Walk to beach, shops, restaurants, entertainments and Grand Hilton * Free fast WiFi. Central A/C. Washer and dryer. * Spectrum Cable and Roku streaming TVs * Private Parking spot 50 yards from the front door

4.89 out of 5 average rating, 152 reviews

The image showcases a spacious home with a covered second-floor balcony overlooking a heated pool. Lush greenery surrounds the well-maintained lawn, while a few lounge chairs are situated near the water's edge, inviting relaxation. Palm trees and tropical foliage frame the scene.

Home in Waikoloa Village

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Beautiful view home 4 bedrooms, Heated Pool! Big private yard, gourmet kitchen, 2 car garage, BBQ. Each bedroom leads out to the lanai(s) through French doors. Comfortably sleeps 8 in beds but can accommodate up to 10 maximum. Less than 10 minutes to awesome beaches, shopping, and restaurants. We now offer air-conditioning for a nominal fee. Please let us know if you would like to add this option to your reservation, the cost is $20/night.

The exterior of a three-story condominium is showcased, surrounded by lush greenery and tropical plants. A well-manicured lawn leads to a ground-level patio with large windows, offering a view of the inviting space within. Sunlight illuminates the façade, enhancing its architectural features.