Holiday rentals with a pool in Kailua-Kona

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.

The Olena at Keauhou Bay

Discover the calm of The Olena, a contemporary 1-bedroom ground floor apartment with A/C, nestled in a quiet complex at the heart of Keauhou in Kailua-Kona. Designed with natural accents and thoughtful details, it is an ideal getaway for 2 guests to enjoy easy walking access to Keauhou Bay and the shops at Keauhou Shopping Center. Enjoy a shared pool, savor sunsets on the expansive lanai with a picturesque view of the Kona Country Club, and immerse yourself in the laid back lifestyle of Hawaii.

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!

Longboard Studio at Kona Magic Sands Beach

Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

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.

Updated condo with ocean views & air conditioning

Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.

Suite Magic Sands Beach

Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

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.

Peaceful Paradise

Experience ALOHA in this spacious, ocean view gem!💎 2 miles to downtown Kona. Comfortable, clean, sun-kissed and welcoming. Perfect for unwinding after a day of island sight-seeing. The charming, stylish space has a private entrance and is located on the ground floor of a large two-story home. You will experience all the comforts of home including an ohana kitchen, living area, bbq, and lovely, large outdoor lanai. Our goal is to give 5 star stays to every guest!

On-the-Ocean, Stunning Corner Unit, Spacious, AC!

Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Unbelievable views from the lanai and living room. Top floor corner unit with windows everywhere so you feel like you are living outside. King bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Ocean-front pool with community BBQ. Quiet; set back from Ali'i Drive. Close to everything--just one mile from downtown Kona. Reserved parking spot. AC.

Halia Hale

Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

Blissful paradise with epic view- Hale Mahana

Serenity in Kona- with epic ocean views! Wake up with the ocean waves crashing below. Hang out on the lanai with some Kona coffee from the Green Flash cafe next door. You have a front row seat for whale watching during whale season. Or, hang out and enjoy the sunsets- at times with our local manta ray! We have a queen sofa bed, and AC. Close to town- an 18 minute walk. Quiet, very little road noise here. You can rent bikes too across the street.