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Holiday houses in Kailua Bay

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Top-rated holiday rentals in Kailua Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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, 357 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

Top Guest favourite
An outdoor space surrounded by lush tropical plants creates a serene atmosphere. A concrete path leads to a seating area with natural wood furniture and a comfortable wicker chair, while soft lighting enhances the inviting environment.
Apartment in Kailua-Kona
4.99 out of 5 average rating, 303 reviews

Private Oasis with FIVE STAR Service and Amenities

See our 6 or 7-NIGHT STAY DISCOUNT - Cleaning fee ONLY $45 - Book now Approx 2hr drive to the volcano from Kona 924sq feet/85sq meters private entrance apartment attached to my house. Three miles/seven minutes from the center of town. Not conducive for walking or biking. Early/Late check-in/out are almost always available. We block 1 to 2 days between guests. If you are a day short at the beginning or end of your intended stay, please contact us and we will open some dates for you if possible.

Top Guest favourite
A spacious wooden deck surrounds a geodesic dome, offering a serene outdoor setting. Two hanging egg chairs are positioned for relaxation, while a portable heater is located nearby. The dome features a transparent facade that reflects sunlight, surrounded by lush greenery.
Dome in Holualoa
5 out of 5 average rating, 240 reviews

The Dome at Ulu Inn: Luxury Couples Retreat, Kona

Overlooking the beautiful Kona Coast...The Dome at Ulu Inn says: "Aloha...let's Disconnect, to Reconnect" Nestled within a gated 5 acre estate, Settle into our exclusive Geodesic Dome suite...experience elevated glamping, designed for ultimate relaxation and ensured seclusion from the outside world. THE DOME & neighboring unit THE CUBE, are an ample distance apart, providing privacy from each other. You may get up close and personal with our Goats, Pigs, Geckos & wild birds that roam freely.

Guest favourite
Condo in Kailua-Kona
4.93 out of 5 average rating, 171 reviews

True Oceanfront, Top-Floor, Downtown, A/C, Parking

Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

Top Guest favourite
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, 781 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 favourite
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
4.99 out of 5 average rating, 363 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 favourite
Condo in Kailua-Kona
4.94 out of 5 average rating, 138 reviews

Downtown 1BR • AC • Pool & BBQ • 1Gb WiFi

Stay productive & relaxed in our upgraded 1BR condo featuring AC, a sparkling pool and 1 Gig ultra-fast WiFi. What guests love: • Queen-size bed, blackout curtains, AC • Fully stocked kitchen, BBQ grills by the pool & beach gear • In-unit laundry • Desk, ergonomic chair & monitor for WFH • Smart TV with streaming, board games for nights in • 1 Free assigned parking spot; 5-min walk to cafés, farmers’ market & waterfront Book with confidence with a Superhost—over 130 five-star stays!

Guest favourite
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
4.95 out of 5 average rating, 216 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.

Guest favourite
A tranquil pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant foliage. Lounge chairs are placed around the pool, where guests are seen enjoying the water and the sunny environment. The two-story building with balconies is visible in the background.
Condo in Kailua-Kona
4.9 out of 5 average rating, 460 reviews

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.

Superhost
A spacious studio is furnished with a queen-sized bamboo bed, complemented by rattan seating and a coffee table. A flat-screen TV is placed on a woven chest of drawers, enhancing a relaxed atmosphere. Natural light filters through the nearby window, illuminating the room.
Condo in Kailua-Kona
4.88 out of 5 average rating, 213 reviews

Walk around KonaTown Restaurants Beach!

Aloha and E Komo Mai! (Welcome) to Kona Escape! This Hawaiiana inspired 1/bed, 1/bath studio condo with convenience kitchen is beautifully decorated, clean and located on Ali'i Drive in the Village. It is across the street from Kailua Bay and walking distance to restaurants, shops, churches, Kailua Pier, night life, beaches and ocean activities. There is also a large Farmers Market nearby. We are across the street from IronMan Swim Start/Finish line.

Top Guest favourite
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, 285 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!

Top Guest favourite
A fully equipped kitchenette features light blue walls, granite countertops, and wooden shelves. Glassware and plants are neatly displayed, alongside a coffee maker and toaster. The space is designed for convenience, enhancing the functionality of the studio.
Apartment in Kailua-Kona
4.99 out of 5 average rating, 131 reviews

Cozy Pineapple Studio 2 Blocks From The Ocean

You'll love the peaceful and chill vibe of the comfy Pineapple Studio, with a private full bathroom and well-appointed kitchenette including an on-demand hot and cold filtered water server. Located less than half a mile from Ali'i drive, it's convenient for exploring restaurants, retail shops, bars, coffee and smoothie spots, fresh farmers markets, beaches, and much more. Click the reserve button below to book your stay with us today.

Popular amenities for Kailua Bay holiday rentals

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