Holiday rentals 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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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.
Apartment 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 favourite
An open living space is presented, featuring a modern kitchen with black cabinetry and stainless steel appliances. Comfortable gray seating is arranged around a circular coffee table, while a staircase leads to an upper level. Natural light fills the area, complemented by green foliage nearby.
Apartment in Kailua-Kona
4.92 out of 5 average rating, 188 reviews

Downtown Kona! Ocean View<1/2mi to Beach!

Say ‘Aloha’ to the good life when you book one of the best located condos in downtown Kailua-Kona! Located in the heart of downtown, this modern loft style home is just a 5-10 minute walk to the beach, the famous Alii Drive, restaurants, and on-the-water fun. Equipped with a private lanai and community amenities, you’ll have everything you need to enjoy Kona to it's fullest. Walk to the best downtown Kona Beach for a fun family-friendly day of sun, white sand, turquoise waters, and snorkeling!

Guest favourite
A private lanai features a round table with two chairs overlooking the ocean. The table is set with plates and glasses, complemented by a bottle of wine. The deep blue water and rocky shoreline are visible in the background, under a clear sky.
Apartment in Kailua-Kona
4.93 out of 5 average rating, 168 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 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 favourite
The living area features a comfortable sectional sofa and a large television with various streaming options. Large windows offer expansive views of the ocean and surrounding greenery, while a dining table and chairs are visible in the background.
Home in Kailua-Kona
4.97 out of 5 average rating, 370 reviews

Kona Sunsets & Ocean Views at Hillside Home

Watch Kona’s world-famous sunsets from two private balconies at this spectacular tropical retreat. Perched on a Hualalai hillside among sleepy palms, this luxury getaway boasts unmatched ocean views. This modern home features a full kitchen, indoor & outdoor dining, 2bd/1.5 bath, office, parking, and free laundry. When the breeze isn’t enough, air-conditioned bedrooms keep you cool. We are proud to be top-rated Airbnb Superhosts and provide you with an award-winning level of service. Aloha!

Guest favourite
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.
Guest house 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 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
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 favourite
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.
Flat 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 favourite
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.
Apartment 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.

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.
Apartment 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.

Guest favourite
A dining table set for breakfast is situated on the lanai, featuring plates, cups, and a glass with a beverage. In the background, lush tropical greenery and the ocean are visible under a clear blue sky.
Apartment in Kailua-Kona
4.89 out of 5 average rating, 184 reviews

Kailua Bay Resort - Hale Ho’omaha

Modern Hawaiian style, freshly updated top floor condo with ocean and mountain views from the lanai. Spacious living, full kitchen, private bedroom, open upstairs loft, 2 bathrooms. Perfectly situated near downtown Kona which hosts an array of restaurants, shopping options, and adventure opportunities such as paddle boarding, snorkeling, and ocean kayaking. Kailua Bay Resort - Hale Ho’omaha, “house of rest” offers everything you need for a relaxing vacation on Big Island.

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.
Apartment in Kailua-Kona
4.88 out of 5 average rating, 207 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.

Popular amenities for Kailua Bay holiday rentals

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