Vacation rentals with a pool in Captain Cook

Family-Friendly Retreat Guest Suite-Pool & Lanai!

Escape to paradise in the heart of coffee country! This private guest apartment in a family home in Holualoa is just 7 miles from Kona. A peaceful retreat for families looking to get away from it all, yet just a scenic 20 minute drive to the conveniences of Kona town. Come back and unwind, enjoy our gardens and take a sunset dip in the pool after a fun-filled day of island adventures. Your Big Island home away from home awaits! Please read the entire listing prior to booking. TA-125-991-5264-01

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.

Aloha Paradise! Remodeled with A/C & Ocean View!

Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

Tropical Private Oasis, Heated Pool & OceanView!

3 bedroom/2.5 bath, Sleeps 8 with Private Solar Heated Pool with Waterfall, Lanai, Gazebo with Ocean View, Tropical Yard. 5 min to downtown Kona along the water. This "model home" sits in a gated community of Kahakai with breathtaking views. It has all upgrades throughout the house for ultimate luxury. A pathway on this 1/2 acre plus property leads to an elevated private gazebo for that amazing romantic evening dinner or relaxing with your special one while looking at an amazing ocean view.

Bungalow Bliss Ocean & Pool View Kailua-Kona HI

Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, & downtown Kailua-Kona! Sun-kissed ocean & pool views await you in this cozy, stylish space. A perfect budget-friendly, clean, cool place to rest between your island adventures! Located near downtown Kailua-Kona and 500 ft above sea level, this property offers cooler temperatures and breezes that delight guests. This suite best fits solo travelers or couples who like to be cozy!

Downtown Kona Plaza Condo w/AC

Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

Hale Kapena (Captain's House)

Hale Kapena (Captain's House) is a cute golf course frontage condo with peekaboo ocean views. This cozy unit features one full bedroom and a convertible second sleeping area in the living room area. Great for visiting guests or children. This ground floor unit offers easy access with a reserved parking place. Hawaii accommodation taxes of 2023 should be be included in quotes. Also early check-in or late check-out, if available, can be requested for additional fees.

Milolii Whale House With Ocean Views and Pool!

The Whale House is a great home to watch the whales migrate down the Kona Coast in season! The house has 3 private bedrooms and 2 1/2 baths on two levels. The upper (primary level) includes a full service kitchen, two master bedrooms and 1 & 1/2 bathrooms. The lower living area is separate from the main living space, is handicap accessible (See Accessibility Notes) and has a private master bedroom and master bath. The house is perfect for couples or families.

Inna's Downtown-Walk to Beach and to Supermarket!

This luxurious condo with custom interior design is located in historic downtown Kona from where you can walk to sandy Kailua Bay beach just 2 blocks away, restaurants, supermarket, shopping and entertainment. The condo features: pool with BBQ deck, private laundry, full kitchen with dishwasher and ice maker, two zoned ultra quiet AC, Cal. King bed, a screened-in Lanai with peekaboo view of the ocean, fiber optic internet, and a 65” 4K smart TV!