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Holiday rentals in Kailua Bay

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Top-rated holiday rentals in Kailua Bay

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Apartment in Kailua-Kona

4.89 out of 5 average rating, 124 reviews

Incredible Downtown Kona /Renovated/New Dual AC

Enjoy this wonderful getaway condo located in the heart of Kailua-Kona. Just steps from Alii Drive, the ocean, Kailua-Kona Pier, grocery stores, farmers markets, restaurants, and coffee stores. Fully renovated. Brand new dual AC (in both living and bedroom). In-unit washer/dryer. High speed wifi. One assigned parking space. Beach gears (snorkeling gears, beach chairs, boogie boards, and beach towels) are ready for you to use. And enjoy the saltwater pool that comes with a grill/picnic deck.

8–15 Jun

$208 SGD per night

Guest favourite

Cottage in Kailua-Kona

4.95 out of 5 average rating, 347 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.

6–13 Apr

$257 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.99 out of 5 average rating, 366 reviews

Inna’s Cottage - Modern, Tropical Getaway

Located conveniently in Kailua-Kona, just minutes from downtown in upscale neighborhood! This 360 sf (34 sq m) studio with private patio, private entrance, air conditioning, private laundry facilities, high speed Wi-Fi, spa-inspired bathroom, queen bed, and a full size kitchen with dishwasher, ice maker, and filtered cold water. Relax in two recliners and enjoy a 65” (165 cm) OLED TV with Internet streaming, Hulu Live, Netflix! Wake up in a tropical garden to a chorus of birds! Aloha!

9–16 Jun

$192 SGD per night

Apartment in Kailua-Kona

4.89 out of 5 average rating, 385 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.

29 Jul – 5 Aug

$225 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.93 out of 5 average rating, 399 reviews

Ohana Suite Close to Town with A/C

This is our ohana suite in a quiet residential area. The suite includes access to your own lanai complete with patio furniture. We are 20 minutes from the international airport and less than a 10 min drive to center of downtown with restaurants and shopping areas. 7 min drive to magic sand beach and only a 15 min walk to Ali'i drive. We live on the property upstairs and you will have your own entrance. There is keyless entry via code for your convenience. A/C available.

16–23 Jul

$160 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.93 out of 5 average rating, 470 reviews

Hale Walua Ocean View Artist's Ohana

Welcome to Hale Walua. We love sharing our Ohana and aloha with fellow travelers. Your apartment has a private entrance, ocean view, gorgeous garden dining areas abundant with flowers and fruit, comfy queen bed, kitchenette, lounge room, wifi, Apple TV and full bath along with all the beach toys you'll need during your visit to Hawaii's Big Island. Beauty and peace abounds. Several world premier beaches are within a 10- 25 minute drive.

9–16 Dec

$215 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.91 out of 5 average rating, 225 reviews

Cozy ohana, close to airport

Aloha, welcome to my cozy ohana! Located just minutes away from the airport and some of our most beautiful beaches. It has 1 queen bed plus a couch for a 3rd person. 2 walk-in closets. Kitchen and bathroom are brand new! Kitchen includes full fridge, microwave, toaster oven, and hot plate. There's free wifi and a smart TV so you can watch your own Netflix, hulu, e.t.c. Private entrance and oh yeah, the best part...AC! Taxes included.

5–12 Oct

$166 SGD per night

Guest favourite

Guest house in Kailua-Kona

4.95 out of 5 average rating, 317 reviews

Cottage with Ocean and Sunset view

Situated on the western side of the island at a cool 1300ft elevation, this is a small cottage suitable for two people. Privacy is the key word. This is a quiet, clean, peaceful place with A/C, near the airport, town + beautiful beaches located in a safe, affluent neighborhood. After the lava eruption on the other side of the island in 2018 subsided, we are now thrilled to have the best air quality and blue skies since 2007!

6–13 Oct

$154 SGD per night

Guest favourite

Guest suite in Hōlualoa

4.97 out of 5 average rating, 475 reviews

Cozy apartment in Holualoa

Aloha and Mahalo for visiting my listing. "Pl.note that I don't have included the State& County Transient /Ge tax ( 17.50%) in my price since it would reflect in the fee you pay to airbnb. I will collect it upon arrival." This place is nesteld on the slope of Hualalei mountain inmidst of coffee farms, from this cooler elevation (1200ft.) it is only 15 min./7 miles to Kailua -Kona, the nearest Beaches and Supermarket.

1–8 Apr

$208 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.97 out of 5 average rating, 143 reviews

Picturesque Private Studio / Panoramic Ocean Views

Breathtaking studio suite perched at 1100 feet elevation in a residential neighborhood of tropical one acre estates, providing privacy, expansive 180 degree ocean views and cool breezes. Enjoy the peaceful sanctuary of your private lanai for sipping your favorite beverage while gazing at the fabulous coastal views and sunsets. You will find everything you need for your vacation or business stay.

12–19 Jun

$201 SGD per night

Guest favourite

Flat in Kailua-Kona

4.95 out of 5 average rating, 428 reviews

"Harbor View Hale" Romantic Retreat

Aloha! Retreat in a romantically-luxurious and renovated 1 Bedroom apt with teak canopy CAL KING bed, stainless steel appliances, washer/dryer, a lanai that overlooks the ocean with view on our lush garden with fruit trees, plants, tropical birds. We feature an in-rental TABLET to provide cutting edge support for your most extraordinary vacation experience. Property Guide, Concierge, etc...

23–30 Jul

$211 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 486 reviews

Cozy, Private Studio with an Incredible View!

Just 10 minutes from Kona International Airport, this private studio is perfectly situated as the start for your Big Island adventure. The space is bright and airy with French doors that open to the lanai for an even more spacious feel. There is a closet, a private washer and dryer, basic amenities, a 65” smart TV, and USB outlets. There is a queen bed and a comfortable couch.

6–13 Mar

$206 SGD per night

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Popular amenities for Kailua Bay holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Kailua Bay

Guest favourite

Dome in Holualoa

5.0 out of 5 average rating, 102 reviews

The Ulu Inn: Luxury Couples Retreat Dome, Kona

2–9 Mar

$407 SGD per night

Apartment in Kailua-Kona

4.8 out of 5 average rating, 280 reviews

Comfy, Clean & stylish condo w/ ocean&sunset views

17–24 Dec

$222 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 198 reviews

Walk to Magic Sands Beach! Prime Location

5–12 Jul

$194 SGD per night

Guest favourite

Guest house in Kailua-Kona

4.96 out of 5 average rating, 156 reviews

Our Hawaii Hale: Detached 2 bed ohana with parking

28 Mar – 4 Apr

$198 SGD per night

Apartment in Kailua-Kona

4.82 out of 5 average rating, 117 reviews

Beautiful Kona Condo in the middle of Ali'i Drive.

17–24 Jan

$212 SGD per night

Guest favourite

Guest suite in Kailua-Kona

5.0 out of 5 average rating, 246 reviews

Your Big Island Escape - King Bed & A/C

2–9 Sep

$211 SGD per night

Apartment in Kailua-Kona

4.82 out of 5 average rating, 150 reviews

2-Unit AC, Full Kitchen, Washer/Dryer, City Center

24–31 Aug

$221 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.9 out of 5 average rating, 374 reviews

Honu Ohana - walk to White Sands

8–15 Aug

$213 SGD per night

Destinations to explore