Holiday rentals in Kailua Bay

4.92 out of 5 average rating, 169 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!

5 out of 5 average rating, 214 reviews

Dome in Holualoa

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.

5 out of 5 average rating, 117 reviews

Cabin in Kailua-Kona

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.

4.86 out of 5 average rating, 214 reviews

In Town ALII ,Oceanview, 1 bdrm Ironman Kona Plaza

This is a lovely, well stocked, 1 bedroom, 1 bath condo. Tastefully decorated with a wonderful Hawaiiana Feel. Enjoy the over sized lanai, with comfortable furnishings, for reading, relaxing and dining. The evenings are peaceful with the waves crashing against the shore The sunsets are amazing, and the mornings are cool and quiet. Sleep well, in a large A/C king sized bedroom Beaches, restaurants, snorkeling, all within a quick walk. OVER IRONMAN THE RATE GOES UP AND IT IS A 9 NIGHTS.

4.97 out of 5 average rating, 185 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.

4.9 out of 5 average rating, 441 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.

4.93 out of 5 average rating, 120 reviews

Downtown | AC | Pool | Kitchen | Desk |1 Gig | BBQ

º 1 Bed / 1 Bath condo with Pool + Hot Tub, BBQ, A/C, Gig WiFi 6E, Full Kitchen, In-unit Laundry, Patio, pull-out couch + queen air mattress º 5 min walk downtown to restaurants, shops, Ali'i & Kona Pier º Fully stocked and equipped kitchen & bathroom º Desk, chair, 2 monitors, color printer, wired ethernet & Wi-Fi; Full length closet º All beach equipment (chairs, umbrella, towels, snorkels, cooler, body board) º Honda Pilot, Honda HR-V, Honda CR-V or Kia Sportage SX for rent

Superhost

4.78 out of 5 average rating, 119 reviews

Condo w/private lanai & a peek-a-view of the pool!

Location! Location! Location! ☀️ Welcome to our centrally located studio condo #318 in the heart of Kona Town! Nestled between Ali’i Drive and Kuakini Hwy, you’ll be within walking distance of Kona’s best restaurants, shops, beaches, and bars. Enjoy swimming & snorkeling at the nearby pier, just a short walk away. Unwind by the pool or hot tub, take an evening stroll for a nightcap, or start your day with a morning walk for a cup of Kona coffee. Your perfect getaway awaits!

4.96 out of 5 average rating, 263 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!

4.97 out of 5 average rating, 104 reviews

Relaxing Ocean Studio Close To The Beach

The comfy and clean Ocean Studio has a private full bathroom and well-appointed kitchenette, including a hot/cold filtered water dispenser. Centrally located in Kona, it's less than half a mile from Ali'i drive where you can explore all the best attractions such as tasty restaurants, retail shops, bars, coffee and smoothie spots, farmers markets, Magic Sands Beach, and much more. Click the reserve button below to book your stay with us today.

Superhost

4.8 out of 5 average rating, 171 reviews

Air Conditioned Beach-Front Gem in Kona Town!

Aloha and E Komo Mai! (Welcome) to Kona Escape! This tranquil studio condo with kitchenette 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.

Guest suite in Kailua-Kona

4.98 out of 5 average rating, 179 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.

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Other great holiday rentals in Kailua Bay

4.96 out of 5 average rating, 46 reviews

Home in Kailua-Kona

Luxury Villa Above Kailua Bay

RozelleRating, 5 stars2 weeks ago

This place was just perfect, close to town yet away from all the noise. Definitely plan on staying here again! George was very quick to respond and a great host overall. The views of the ocean were amazing. We loved waking up and drinking our coffee on the lanai and enjoying the view. Place was comfortable and spacious.

5 out of 5 average rating, 13 reviews

Kona Hale 9

JeremyRating, 5 stars1 month ago

Great location, clean, was as described. Only downside is the walls are thin as said in previous reviews.

4.97 out of 5 average rating, 97 reviews

Centrally Located Downtown Kona Condo

BrendaRating, 5 stars1 month ago

Had a great stay, clean and great location.

4.99 out of 5 average rating, 75 reviews

Home in Kailua-Kona

The Mango Cottage on Keauhou Bay

KaylieRating, 5 stars3 weeks ago

Peter and Lori are friendly and welcoming and their property is truly lovely -- it is evident that a lot of care, effort and thought goes into to maintaining it. The cottage makes a perfect home base for exploring the area. It is also so pretty and comfortable that you just might want to pick up a pizza, watch some Jeopardy and dream about what it would be like if every Friday evening was that perfect :) Thank you so much Peter & Lori!

4.86 out of 5 average rating, 121 reviews

Downtown Kona Condo / Vintage Hawaii / Fast WiFi

NatalieRating, 5 stars1 week ago

Perfect place to hang your hat when visiting Kona. The beach/restaurants/shops are literally right down the hill and it's smackdab in the middle of so many amazing beaches. Kahalu'u and Waialea are a MUST if you like snorkeling! Don't worry about packing or renting any gear because that's all fully stocked. Felt like a home away from home. An AC unit was added to the main living space since some of the other reviews so it was nice and cool. There are grocery stores minutes away and the kitchen has everything you could need. It's an older residential property, so you can hear your neighbors, but they were all friendly and it felt very safe.

5 out of 5 average rating, 27 reviews

Brand NEW Oceanfront Retreat! Steps to Beach!

ChelseaRating, 5 stars2 weeks ago

Very responsive, and kind! Loved my stay at this Airbnb, the weather wasn’t that great for my visit but the Airbnb made it better! View was great, looked just like the pictures!

4.97 out of 5 average rating, 29 reviews

1BR Kona Condo w/ Chef’s Kitchen & Tropical Lanai

JuanitaRating, 5 stars2 weeks ago

Ina is a very informative and responsive host. She recommended some great local restaurants and places to hang out. The house is clean and the neighborhood is very peaceful. There is a beautiful view of the beach behind the apartment (2 minutes walk). The kitchen is fully equipped with utensils and ingredients. However, we didn't have time to cook. One thing we found annoying was that the AC was portable and a bit noisy.