Vacation rentals in Kailua Bay

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Top-rated vacation rentals in Kailua Bay

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Top guest favorite
A comfortable sleeping area features a spacious queen bed adorned with a white quilt. A cozy sitting area is visible with a light green couch and a small coffee table. Warm light from a lamp illuminates the room, complemented by tropical artwork on the walls.
Condo in Kailua-Kona
4.99 out of 5 average rating, 348 reviews

Oceanfront/Hawaiian Charm W/Modern Amenities

Welcome to Hale Kani Moana (House of Ocean Sounds❤️)…the best location, city center on world famous Ali’i Drive. Cozy Hawaiian Charm w/ modern amenities. At your doorstep are the best restaurants, nightlife, and shopping. Stunning oceanfront unit w/sunset views (Fall/Winter). Listen to the ocean waves gently crash as you fall asleep. Fully stocked kitchenette, bathroom/shower, and all the beach equipment you’ll need. FREE Parking+FAST Wifi :-) Note: 3rd (Top Floor) stairs only, no elevators

Guest favorite
A spacious bed is adorned with patterned bedding and a decorative yellow pillow. Framed by two pendant lights, a nature-themed artwork hangs above the headboard. A bench with tufted upholstery is positioned at the foot of the bed, complementing the room's serene design.
Condo in Kailua-Kona
4.82 out of 5 average rating, 146 reviews

Studio condo, King bed, pool view on Alii Drive

Super convenient and affordable studio in the heart of Kona. Only a few minutes' walk to all the best oceanfront restaurants, bars and coffee shops on Alii Drive. Our unit is a ground floor end unit with a view of the pool and hot tub from the back Lanai. Located at the front of the complex near the parking and lobby. There is AC, a 50 inch smart TV, free Wi-Fi. The Kitchenette features a microwave, coffee maker, electric skillet, refrigerator and cups, plates and silverware. TA-032-125-9008-01

Guest favorite
A private lanai is displayed, furnished with a wooden dining table and two chairs. The table is set with plates and mugs. Lush greenery and palm trees surround the space, offering a view of the ocean in the distance under a clear blue sky.
Apartment in Kailua-Kona
4.94 out of 5 average rating, 484 reviews

"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.

Top guest favorite
A charming cottage with a red exterior features large windows and a welcoming porch. Surrounded by lush greenery and native plants, a well-maintained yard is visible. A paved driveway leads up to the cottage, complemented by a stone wall in the background.
Cottage in Kailua-Kona
4.94 out of 5 average rating, 429 reviews

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.

Top guest favorite
A private lanai is enclosed by a decorative railing, offering expansive views of the ocean and vibrant tropical plants. Wicker seating is arranged for relaxation, complementing the serene outdoor setting bathed in natural light.
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 772 reviews

Private Kona Oceanview Retreat with parking

Escape to a private oceanview retreat in North Kona! This cozy guesthouse offers breathtaking views from your private deck, surrounded by lush tropical plants. Enjoy your morning coffee while soaking in the serene ocean scenery, and unwind in a tastefully decorated interior with all essentials, a well-equipped kitchen, modern bathroom with a luxurious shower, and convenient laundry facilities. Perfect for couples or solo travelers and easy access to Kona’s attractions! Tax ID W01822068-01

Top guest favorite
A wooden sign carved with the word 'ALOHA' is displayed against a backdrop of dark volcanic rocks. Colorful hibiscus flowers are painted on either side of the sign, adding a tropical touch to the natural surroundings.
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 242 reviews

Tiny House in Kona - 5 Minute Walk to the Beach!

Mahalo nui for your Interest! After a short break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1400+ 5-Star Reviews and book with Confidence! This is a real Tiny House on Wheels with an additional connected open air and fully screened kitchen for dining and relaxing. You'll love this "rustic" and private experience in an upscale neighborhood just 4 miles south of downtown Kona! And, you are only a 5 Minute Walk to Magic Sands - the best beach in town!

Top guest favorite
A colorful quilt covers a spacious bed, complementing the serene atmosphere of the room. A wall-mounted television displays a scenic image. Large glass doors provide access to a private lanai with ocean views, creating a bright and inviting space.
Guest suite in Kailua-Kona
5 out of 5 average rating, 352 reviews

Your Big Island Escape - King Bed & A/C

Kona sweet spot with private lanai, amazing ocean view, ideal temperatures & personal parking spot. Devoted Super-hosts on-site to maximize your accommodations & experience. Very safe neighborhood. Lots of amenities / beach gear. Only 6 minutes to beaches & great snorkeling, 10 minutes to downtown for diverse food options, shopping & historic sites. Exquisite Kohala beaches 30 minutes north. Popular Walua Trail just 2 blocks away to stroll or jog. * Please no 3rd party bookings. Mahalo.

Top guest favorite
A vibrant tropical garden surrounds a modern villa, nestled within lush greenery and mature palm trees. A serene pool glimmers in the sunlight, creating a peaceful focal point amidst the rich landscaping. The sky above is bright with scattered clouds, enhancing the tranquil atmosphere.
Apartment in Kailua-Kona
4.96 out of 5 average rating, 107 reviews

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.

Guest favorite
A private lanai features a wooden table and two chairs, surrounded by tropical plants and palm trees. A view of the ocean and landscaped gardens is visible in the background, with bright blue skies complementing the tranquil setting.
Condo in Kailua-Kona
4.89 out of 5 average rating, 201 reviews

Cozy Oceanfront, 1Qn bed, 1Qn Sofa bed. Paradise

Completely remodeled (August 2020) 2nd floor Oceanfront studio (within feet of the ocean) is located in the Kona Islander Inn complex that extends from Kuakini Hwy to Alii Drive. The beautiful tropical gardens with banana trees, exotic flowers and green lawns surround you as you find your way to the Pool, Jacuzzi, and Barbecue area. You may never want to use your car once you settle in because many of the finest restaurants, great dancing and live entertainment are within a short walk.

Top guest favorite
A vibrant sunset fills the sky with orange and pink hues, contrasted by the silhouette of a historic church with a tall spire. Lush palm trees frame the scene, adding to the tropical atmosphere as the day transitions into evening.
Condo in Kailua-Kona
4.97 out of 5 average rating, 206 reviews

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.

Top guest favorite
A modern kitchen is visible, featuring white cabinetry, sleek black appliances, and a glossy countertop. A dining area with bar seating is positioned near a cozy living space, which includes a light-colored couch and large ottoman, complemented by soft lighting along the walls.
Condo in Kailua-Kona
4.96 out of 5 average rating, 280 reviews

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!

Guest favorite
A bright studio space features a spacious bed adorned with tropical-themed bedding. Comfortable seating is provided near a large window, with natural light filtering through sheer curtains. A dining table is visible in the background, creating a cozy atmosphere. Decorative art pieces add character to the walls.
Condo in Kailua-Kona
4.9 out of 5 average rating, 115 reviews

Downtown Kona studio, steps from beach, quiet

Unwind in this completely remodeled downtown Kona studio, across the street from the beach -- and a quick walk to cafes, bars and restaurants. This second story corner unit -- decorated in a tropical theme -- is the perfect place to relax after a day of nearby sight-seeing and ocean adventures. Enjoy the glow of Tiki torches around the pool and hot tub from your lanai surrounded by a lush native garden in this old-style Hawaiian complex.

Popular amenities for Kailua Bay vacation rentals

  1. Airbnb
  2. United States
  3. Hawaii
  4. Hawaii County
  5. Kailua-Kona
  6. Kailua Bay