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Kailua-Kona Vacation Rentals

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Kanaloa at Kona by Castle

Kanaloa at Kona by Castle

3 out of 5
78-261 Manukai Street, Kailua-Kona, HI
The price is CA $283 per night from Mar 27 to Mar 28

Situated by the ocean, this condo resort is 0.5 mi (0.8 km) from Keauhou Bay Beach and within 3 mi (5 km) of Kahalu'u Beach Park and Magic Sands Beach. Haleo ...…

3.6/5Good! (276 reviews)
Extremely Nice!

"It was really nice. Much too big for me. I loved the waves crashing on the lanai. It was a very healing experience."…"

Reviewed on Jan. 10, 2021

Kanaloa at Kona by Castle
Kona Reef Resort

Kona Reef Resort

3 out of 5
75-5888 Alii Dr, Kailua-Kona, HI

Located in Kailua-Kona, this beachfront condo building is in the city center and within 1 mi (2 km) of Honl's Beach and Kailua-Kona Wharf. Swing Zone and Magic ...…

4.3/5Excellent! (133 reviews)

"Really beautiful, relaxing setting, convenient location near local restaurants. The condo was clean and came with all necessary amenities. Very quick response from desk concerning brief wireless outage. Polite service. The bed was very uncomfortable like a giant pillow case stuffed with pillows. ..."…"

Reviewed on Feb. 8, 2021

Kona Reef Resort
Aston Kona by the Sea

Aston Kona by the Sea

3 out of 5
75-6106 Alii Dr, Kailua-Kona, HI

Located in Kailua-Kona, this beachfront condo building is in the historical district and within 3 mi (5 km) of Honl's Beach, Magic Sands Beach, and Kailua-Kona ...…

4.3/5Excellent! (924 reviews)

"Great location and views from the balconies- plan to stay there again."…"

Reviewed on Nov. 28, 2020

Aston Kona by the Sea
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Castle Kona Bali Kai , a Condominium Resort

Castle Kona Bali Kai , a Condominium Resort

3 out of 5
76-6246 Alii Dr, Kailua-Kona, HI

Nestled on the beach, this Kailua-Kona condo building is within 3 mi (5 km) of Magic Sands Beach, Kahalu'u Beach Park, and Kailua-Kona Wharf. Honl's Beach and ...…

3.3/5 (1,294 reviews)
Great property, amazing location, property manager very helpful. Would stay again. 5 star all arou!

"Great centralized location for exploring the big Island or just relaxing on property. Within 2 hours of anywhere on the island. Right on the water in with a second floor view of wildlife and beautiful sunsets. We saw whales, fish, turtles from the balcony. This property was stocked with everything ..."…"

Reviewed on Jan. 28, 2021

Castle Kona Bali Kai , a Condominium Resort
Direct Oceanfront 2BR/2BA Townhouse with Pool and Tennis Courts

Direct Oceanfront 2BR/2BA Townhouse with Pool and Tennis Courts

Kailua-Kona, HI
The price is CA $284 per night from Mar 8 to Mar 9

Located in Kahaluu Bay, this romantic vacation home is within a 15-minute walk of Keauhou Shopping Center and Kahalu'u Beach Park. Magic Sands Beach is 1.7 mi ...…

4.6/5Exceptional! (63 reviews)

"Great location. Easy, reliable and friendly communication with the property owners."…"

Reviewed on Jun. 23, 2020

Direct Oceanfront 2BR/2BA Townhouse with Pool and Tennis Courts
Royal Sea Cliff Kona by Outrigger

Royal Sea Cliff Kona by Outrigger

3 out of 5
75-6040 Alii Dr, Kailua-Kona, HI

Situated on the waterfront, this eco-friendly condo building is 0.7 mi (1.1 km) from Honl's Beach and within 3 mi (5 km) of Kailua-Kona Wharf and Magic Sands ...…

4.1/5Very Good! (354 reviews)

"Great property, comfortable and extremely quiet. The staff was helpful and friendly and responded quickly to our needs. I would definitely stay here again."…"

Reviewed on Jan. 29, 2021

Royal Sea Cliff Kona by Outrigger
Kanaloa at Kona by Outrigger

Kanaloa at Kona by Outrigger

3 out of 5
78-261 Manukai St, Kailua-Kona, HI

Situated in Kailua-Kona, this golf condo building is 0.3 mi (0.5 km) from Keauhou Bay Beach and within 3 mi (5 km) of Kahalu'u Beach Park and Magic Sands Beach. ...…

4.2/5Excellent! (466 reviews)

"The location and view were excellent. The size of the condo was great. However, the dishwasher worked, but a strong smell of mold was present when it was opened and it was not secured and the entire dishwasher would fall forward when the drawers were opened. The clothes washer was inoperable and ..."…"

Reviewed on Nov. 2, 2020

Kanaloa at Kona by Outrigger
Kona Reef, A Raintree Vacation Club Resort

Kona Reef, A Raintree Vacation Club Resort

3 out of 5
75-5888 Alii Drive, Kailua-Kona, HI

Situated by the ocean, this condo building is within 1 mi (2 km) of Honl's Beach and Kailua-Kona Wharf. Swing Zone and Magic Sands Beach are also within 3 mi ...…

4.4/5Excellent! (84 reviews)

"Beautiful and convenient location, with free parking and minimal "resort fee." Staff very helpful and friendly. Absolutely loved our stay here."…"

Reviewed on Dec. 22, 2020

Kona Reef, A Raintree Vacation Club Resort
Castle Kona Reef, a Condominium Resort

Castle Kona Reef, a Condominium Resort

3 out of 5
75-5888 Alii Dr, Kailua-Kona, HI

Located in Kailua-Kona, this beachfront condo building is in the historical district and within 1 mi (2 km) of Honl's Beach and Kailua-Kona Wharf. Swing Zone ...…

3.8/5Good! (677 reviews)

"I only like the pool tho! But I didn’t like that if I need it anything I didn’t have no one to ask for it!"…"

Reviewed on Feb. 16, 2021

Castle Kona Reef, a Condominium Resort
Waterfall House 4 Bedroom Home

Waterfall House 4 Bedroom Home

4 out of 5
78-6814 Keaupuni Street, #78 (KEWH), Kailua-Kona, HI

Situated in Kailua-Kona, this golf vacation home is 1.1 mi (1.8 km) from Original Hawaiian Chocolate Factory and within 3 mi (5 km) of Kahalu'u Beach Park and ...…

Waterfall House 4 Bedroom Home
Keauhou Kona Surf & Racquet Club#37

Keauhou Kona Surf & Racquet Club#37

4 out of 5
78-6800 Alii Drive, Kailua-Kona, HI

Situated in Kailua-Kona, this golf vacation home is steps from Kamakahonu Beach and Kailua-Kona Wharf. Swing Zone is 0.9 mi (1.5 km) away.…

Keauhou Kona Surf & Racquet Club#37
Jilly Bean"s Condo, fresh and new remodeled, on Ali'i Drive

Jilly Bean"s Condo, fresh and new remodeled, on Ali'i Drive

Kailua-Kona, HI

Located in the heart of Kailua-Kona, this condo building is within a 15-minute walk of Mokuaikaua Church and Kailua-Kona Wharf. Swing Zone is 1.3 mi (2.1 km) ...…

4.8/5Exceptional! (78 reviews)
Nice place, great location.

"The room was nice and so convenient for everything we wanted to do. Owner was responsive. I didn’t have good cell reception which made communication a bit tricky."…"

Reviewed on Feb. 13, 2021

Jilly Bean"s Condo, fresh and new remodeled, on Ali'i Drive
Keauhou Kona Surf & Racket Club Townhouse #3

Keauhou Kona Surf & Racket Club Townhouse #3

4 out of 5
78-6800 Alii Drive, Unit #3, Kailua-Kona, HI

Situated in Kailua-Kona, this golf vacation home is steps from Kamakahonu Beach and Kailua-Kona Wharf. Swing Zone is 0.9 mi (1.5 km) away.…

5/5Exceptional! (1 review)

"Ocean side Townhouse, really the ocean and surf was right there! We loved the sound of the surf always."…"

Reviewed on Dec. 28, 2019

Keauhou Kona Surf & Racket Club Townhouse #3
Kona Shores #203

Kona Shores #203

3.5 out of 5
75-6008 Alii Drive #203, Kailua-Kona, HI

Situated in Kailua-Kona, this apartment building is 0.5 mi (0.9 km) from Honl's Beach and within 3 mi (5 km) of Kailua-Kona Wharf and Magic Sands Beach. Swing ...…

Kona Shores #203
Keauhou Kona Surf & Racquet Club #176

Keauhou Kona Surf & Racquet Club #176

4 out of 5
78-6800 Alii Drive, Kailua-Kona, HI

Situated in Kailua-Kona, this golf vacation home is steps from Kamakahonu Beach and Kailua-Kona Wharf. Swing Zone is 0.9 mi (1.5 km) away.…

Keauhou Kona Surf & Racquet Club #176
Quiet Cozy Studio - 5 Minute Walk to Beaches and Kahaluu Free Wifi

Quiet Cozy Studio - 5 Minute Walk to Beaches and Kahaluu Free Wifi

Kailua-Kona, HI

Located in Kahaluu Bay, this historic apartment building is within a 15-minute walk of Magic Sands Beach and Kahalu'u Beach Park. Keauhou Shopping Center and ...…

4.7/5Exceptional! (80 reviews)
Nice place in town!

"Looking for a clean place to stay while in Kailua-Kona? This place will fit that bill. There are a few units in the building and the one my wife and I stayed in was completely comfortable. Loved the ceiling to floor screens and the two ceiling fans to keep the air moving. The bed was outstanding ..."…"

Reviewed on Feb. 23, 2021

Quiet Cozy Studio - 5 Minute Walk to Beaches and Kahaluu Free Wifi
Keauhou Surf & Racquet Townhouse #36

Keauhou Surf & Racquet Townhouse #36

3.5 out of 5
78-6800 Alii Drive, UNIT#36, Kailua-Kona, HI

Situated in Kailua-Kona, this golf condo building is steps from Kamakahonu Beach and Kailua-Kona Wharf. Swing Zone is 0.9 mi (1.5 km) away.…

Keauhou Surf & Racquet Townhouse #36
Kahaluu Bay Villas #304

Kahaluu Bay Villas #304

3.5 out of 5
78-6715 Alii Drive, #304, Kailua-Kona, HI

Situated in Kailua-Kona, this golf condo building is steps from Kamakahonu Beach and Kailua-Kona Wharf. Swing Zone is 0.9 mi (1.5 km) away.…

Kahaluu Bay Villas #304
Downtown Kona. 250 Feet From Your Toes in the Water With an Unobstructed View!

Downtown Kona. 250 Feet From Your Toes in the Water With an Unobstructed View!

Kailua-Kona, HI

Situated on the waterfront, this condo building is within a 15-minute walk of Mokuaikaua Church and Kailua-Kona Wharf. Swing Zone is 1.4 mi (2.2 km) away.…

4.6/5Exceptional! (23 reviews)
great location with soft bed but the lanai door lock is broken

"This place has all the essentials plus some (beach chairs, pool noodles, cooler, boogie boards, etc.). The bed was heavenly soft and comfortable. More than enough pillows and blankets. Do not depend on the air conditioning unit for comfort. It turns on but does not cool down the room sufficiently. ..."…"

Reviewed on Jan. 10, 2021

Downtown Kona. 250 Feet From Your Toes in the Water With an Unobstructed View!
A/C and Ocean front pool, 1bedroom Condo on Ali’i drive in the heart of Kona ❤️

A/C and Ocean front pool, 1bedroom Condo on Ali’i drive in the heart of Kona ❤️

Kailua-Kona, HI
The price is CA $139 per night from Mar 2 to Mar 3

This family-friendly Kailua-Kona condo building is located by the ocean, within 2 mi (3 km) of Honl's Beach and Kailua-Kona Wharf. Magic Sands Beach and Swing ...…

4.5/5Wonderful! (17 reviews)
A hidden jem

"It was a nice convenient place to stay. Would definitely visit again."…"

Reviewed on Jul. 8, 2020

A/C and Ocean front pool, 1bedroom Condo on Ali’i drive in the heart of Kona ❤️
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Kailua-Kona you may be interested in

Royal Kona Resort

Royal Kona Resort

3.5 out of 5
75-5852 Alii Dr, Kailua-Kona, HI
Free cancellationReserve now, pay when you stay
The price is CA $221 per night from Mar 5 to Mar 6
Royal Kona Resort
Courtyard by Marriott King Kamehameha's Kona Beach Hotel

Courtyard by Marriott King Kamehameha's Kona Beach Hotel

3.5 out of 5
75-5660 Palani Road, Kailua-Kona, HI
Free cancellationReserve now, pay when you stay
The price is CA $251 per night from Feb 27 to Feb 28
Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kailua-Kona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Kailua-Kona?
Yes, we have vacation rentals in Kailua-Kona close to Kona Le’a Plantation, or you can choose a secluded option if you’d like a relaxing place to stay. Visitors like the array of shops and popular beaches in Kailua-Kona. While you’re here, grab a bite or have a drink at the charming coffeehouses and top-notch restaurants.
What are some of the best vacation home rentals that Kailua-Kona has to offer?
Waterfall House 4 Bedroom Home: Visitors like this Kailua-Kona vacation home rental. It is located next to a golf course and has a hot tub, a barbecue grill, and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a coffee maker. Some other homes for rent in Kailua-Kona include Direct Oceanfront 2br/2ba Townhouse With Pool and Tennis Courts and Pu’u Kole Street Home Unit 106 by RedAwning.
How many vacation rentals will I find in Kailua-Kona?
With 634 Expedia vacation rentals, you’re sure to find just the right place for your Kailua-Kona stay.
What can I see and do in Kailua-Kona?
Family-friendly attractions include Kona Le’a Plantation and Mountain Thunder Coffee Plantation, whereas Kua Bay and Magic Sands Beach are a couple of great spots to enjoy the outdoors. You can also visit some other popular places in town, such as Big Island Country Club and Kailua-Kona Wharf.
What are vacation rentals like in Kailua-Kona?
Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Kailua-Kona. Vacation rentals feature amenities like WiFi and washers and dryers so you’ll have all the conveniences of home. If you’re concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You’ll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips.