Holiday rentals in Kailua Bay

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!

"Harbor View Hale" Romantic Retreat

Aloha! Escape to this romantic, luxuriously designed 1-bedroom retreat with A/C. Sleep soundly in a teak canopy Cal King bed, cook in a sleek kitchen with stainless steel appliances, and enjoy the convenience of an in-unit washer/dryer. Relax on your private lanai with stunning ocean views overlooking a lush tropical garden full of fruit trees and birdsong. A custom *tablet* offers local tips, property info, and more. Guests love the cool comfort and authentic vibe of our Hawaiian neighborhood.

Radiant Ocean View Cottage on a Coffee Farm. Very Private.

Centrally located between South Kohala's beaches, and the dining and entertainment scene of Kailua-Kona, the Kaloko Coffee Cottage is at a cool elevation making naps after adventures a...well a dream! Far from any roads, the dominant sounds are the many birds who make their homes in the surrounding trees. This is a thoughtfully furnished home with an open layout, on a coffee farm, just bring your food and clothes for which ever adventure you intend; leave the accommodations and ambiance to us.

Kona Ocean Front Cottage on Keauhou Bay

Waterfront cottage on private, gated 1 acre estate. Close as you can get to an over the water bungalow in Hawaii with direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. Queen bed. Living room with 50 in TV. Bathroom with large shower. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower.

Romantic Cabin Treehouse in Hawaii Cloud Forest

Stay in a unique cloud forest at a 2500 foot elevation, yet minutes to airport, beaches, restaurants, bars and shops. Extraordinary lodging, perfect for a honeymoon, writers retreat or meditation vacation. Surrounded by native forest, with tree fern and Hawaiian song birds. Afternoon rains end in grand sunsets. Nights are cool for sleeping with windows open. State forest hiking trails are at your doorstep. Great bird watching, including a local flock of cockatoos that visit in the morning!

Romantic Kona Hideaway | Modern + Private Hot Tub

Tucked away in a peaceful native Hawaiian forest, this modern hideaway offers the perfect romantic escape just 10 miles from Kona’s beaches, airport, and town. Thoughtfully designed for couples, honeymooners, and those craving serenity, this stand-alone retreat blends minimalist style with beauty. Unwind in the private hot tub surrounded by nature, watch sunsets from the lanai, or grill under the stars. Inside, enjoy 384 sq. ft. of creative space that captures luxury, nature and seclusion.

Oceanfront Gem, Walk to Beach/Town, AC, Elevator

Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

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.

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.

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Hale Kamalei in Kailua Kona

Enjoy all the comforts of home in this stylish guesthouse in the heart of Kailua Kona. This detached one bedroom ohana is centrally located - just minutes from the airport, shops, restaurants and some of the best beaches on Hawai'i Island. Experience Hawaii away from the hustle and bustle of resorts and overcrowded condominiums and stay where the locals live! The designated parking space is just steps from the front door. Private, clean, and convenient.

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.