Kaupulehu Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Kaupulehu

Aston Kona by the Sea
4.0 star property
8.8 out of 10, Excellent, 982 reviews
"Awesome!"
The price is CA $519
CA $814 total
includes taxes & fees
Jun 1 - Jun 2
Aston Kona by the Sea
Kanaloa at Kona by Castle
3.0 star property
7.6 out of 10, Good, 391 reviews
"Very nice property thank you 🤗"
Kanaloa at Kona by Castle
Royal Sea Cliff Kona by OUTRIGGER
3.0 star property
8.4 out of 10, Very good, 432 reviews
"Beautiful"
Royal Sea Cliff Kona by OUTRIGGER
Save an average of 15% on thousands of hotels when you're signed in
Kanaloa at Kona by OUTRIGGER
3.0 star property
8.4 out of 10, Very good, 471 reviews
"This was a great property. The grounds and condo were beautiful. Small amount of beach stuff to use. Washer and dryer came in handy. It would have been nice to have some tupperware or foil in the kitchen. The walls are thin and we could hear every step made upstairs. There is a nice quiet bay within walking distance. "
Kanaloa at Kona by OUTRIGGER
Castle Hali'i Kai at Waikoloa
4.0 star property
9.0 out of 10, Wonderful, 629 reviews
"Beautiful place to stay but communication with the staff is difficult because office hours is 10 to 6 only. Don’t even put a number where you can contact after hours. I arrived at the property after 6 and l was struggled to find out how to check into my unit not knowing that they emailed me an instruction how to get into my unit"
Castle Hali'i Kai at Waikoloa
Sea Village
2.5 star property
9.2 out of 10, Wonderful, 15 reviews
"Check in was snow, the room guaranteed by 4:00 pm, I was there at 3:40pm and they won’t let us to the room till 4:00pm, this resort didn’t provide shampoo and conditioner, it is kind of weir."
The price is CA $259
CA $305 total
includes taxes & fees
Jun 6 - Jun 7
Sea Village
Kona Reef, A Raintree Vacation Club Resort
3.0 star property
8.4 out of 10, Very good, 312 reviews
"I loved it"
Kona Reef, A Raintree Vacation Club Resort
Fairway Villas Waikoloa by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, 455 reviews
"Well equipped, and clean condo (we got a three BR, two level) with sliders to back patio table and recliners overlooking beautiful surrounding grounds, a golf course (which our family golfers said was great), a community infinity pool/jacuzzi a short walk away, small open air gym and bbq area with 6 grills for use near the pool area. Only issue was transportation to condo from check-in office in shopping center which is within 5 minute walking distance, but difficult if walking with luggage. ...
Fairway Villas Waikoloa by OUTRIGGER
Mauna Lani Point
4.0 star property
9.2 out of 10, Wonderful, 262 reviews
"Comfortable, clean, quaint, well-equipped unit! Marvallee was wonderful with communication! Location is EXCELLENT!!!"
Mauna Lani Point
Newly updated condo in the heart of downtown Kona. One block from the beach
9.8 out of 10, Exceptional, 13 reviews
"Location is perfect! Totally enjoyed the apartment, very clean and relaxing. Nice quiet and the screened in balcony is a plus!"
Newly updated condo in the heart of downtown Kona. One block from the beach
Kona Islander Inn Condo, fresh and new remodeled, on Ali'i Drive
9.6 out of 10, Exceptional, 162 reviews
"The unit was very clean. It had everything needed for an awesome stay. Plenty of shopping and restaurants very close. Across the street from the ocean. Loved being on the ground floor. I would stay here again."
The price is CA $150
CA $364 total
includes taxes & fees
Jun 3 - Jun 4
Kona Islander Inn Condo, fresh and new remodeled, on Ali'i Drive
Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.
10.0 out of 10, Exceptional, 135 reviews
"We had an amazing stay at this property. Exceeded our expectations from the pictures online. We loved being able to hang out in the several lounging spots at the house, being able to walk the beach and tidepools directly in front of the home and easily walk to town. We didn't feel like we needed to leave the property it was so great. Mei, the property manager helped us immediately and gave recommendations. We would absolutely book again."
Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.
Kona Mansions#301 Top Floor, Corner Unit w/Ocean views & AC
9.6 out of 10, Exceptional, 32 reviews
"Everything was great, from the cleanliness, to the prompt communication with the staff when any questions were had. It was a nice addition to have swim/snorkel accessories, such as the boogey boards, swim noodles, sun screen, etc. Definitely had a comfortable stay and would stay here again."
Kona Mansions#301 Top Floor, Corner Unit w/Ocean views & AC
Mauna Kea Residences
4.0 star property
10.0 out of 10, Exceptional, 27 reviews
"The beach on the property was awesome. The guys on the ATV's on the beach need to minimize there trips past the chairs with umbrellas, they went back and forth too much. They also need to travel down the sides of the chairs not through the middle divide of the chairs. "
Mauna Kea Residences
Contemporary Studio 1 minute to the Ocean!
9.0 out of 10, Wonderful, 51 reviews
"Very nice unit with a nice view of the pool. As other people has stated parking is challenging. But I always found a place in the lot or right next to the property on the street. The bed is comfortable and I slept well. Minor issue with some small ants in the bathroom.owner was very responsive. I would definitely stay here again."
The price is CA $157
CA $337 total
includes taxes & fees
Jun 13 - Jun 14
Contemporary Studio 1 minute to the Ocean!
HO'OMAHA! *Well equipped, Cozy Condo* Steps from Ali'i drive, Kailua-Kona town
9.4 out of 10, Exceptional, 155 reviews
"While not for the view, it is clean and reasonably appointed with a short walk to coast and main drag in Kona. Pullout couch works for a teen. Roomy enough. Nice shower. Our only real issue was a water outage during stay which was very inconvenient but probably beyond the control of host. Would return."
HO'OMAHA! *Well equipped, Cozy Condo* Steps from Ali'i drive, Kailua-Kona town
2BR/2BA Kona Reef Ocean & White Sand Beach From Every Room
9.2 out of 10, Wonderful, 181 reviews
"This was a perfect destination for my family and i. Kitchen set up.for full meals, clean, spacious, and oh man the views. The sunsets off the lanai were spectacular. Easy walking to everything in town, and a great starting point for longer destinations. Beach outside the door, waves crashing, it was awesome. Easy to get to, only caveat is you need to be a pretty good at parking in tight spots. The garage is clean, safe, and small. Other than that, awesome all around."
2BR/2BA Kona Reef Ocean & White Sand Beach From Every Room
Fresh tropical stay with pool and hot tub access, large lanai, W/D - golf nearby
9.4 out of 10, Exceptional, 8 reviews
"We enjoyed our stay at the condo. Very comfortable and walking distance from grocery store and eateries. Thank you for providing the welcome goodies! We woo love to stay again."
Fresh tropical stay with pool and hot tub access, large lanai, W/D - golf nearby
Direct Oceanfront Condo! Sea Turtles & Beautiful Sunsets from the Lanai
9.6 out of 10, Exceptional, 118 reviews
"My husband and I honeymooned here in early May 2024. The pictures on the listing are EXACTLY what to expect we were so excited to see the view in person. The building itself is a little dated, but as soon as we got to our room we completely forgot about it. When we first arrived we were nervous about the noise level we would hear from being so close to the street, however the waves themselves were so loud we couldn’t hear anything over them. Kitchen was perfect for our breakfasts and lunches,...
The price is CA $280
CA $638 total
includes taxes & fees
Jun 23 - Jun 24
Direct Oceanfront Condo! Sea Turtles & Beautiful Sunsets from the Lanai
Castle at Kona Reef
3.0 star property
7.6 out of 10, Good, 602 reviews
"This was our second time staying at the Kona Castle Reef . This oceanfront unit was comfortable, tidy and an excellent layout. Some of the lighting fixtures seemed dated and Could use replacement . Having the bbq’s there as an alternative cooking option was fantastic. We can’t wait to visit again next year and hopefully secure the same unit as we did this time ."
Castle at Kona Reef
Don't see what you're looking for?
See all available properties in Kaupulehu
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 Kaupulehu you may be interested in

Four Seasons Resort Hualalai
5.0 star property
9.6 out of 10, Exceptional, 425 reviews
"Best resort in all of HI, maybe the U.S. "
The price is CA $1,642
CA $1,948 total
includes taxes & fees
Jun 1 - Jun 2
Four Seasons Resort Hualalai
Kona Village, A Rosewood Resort
5.0 star property
9.0 out of 10, Wonderful, 18 reviews
"Our stay was incredible. Lovely beaches and pools, impeccable service, and beautiful, spacious rooms. Facilities like the spa and gym were top notch, refined and stylish without being fussy. Would stay here again in a heartbeat, highly recommend for anyone looking for a quiet, stress free stay."
The price is CA $1,535
CA $1,811 total
includes taxes & fees
Jun 1 - Jun 2
Kona Village, A Rosewood Resort
Royal Kona Resort
3.5 star property
8.2 out of 10, Very good, 2,531 reviews
"This property was in a beautiful area with many opportunities for dining and shopping within a few minutes walking distance. The rooms were clean and nice and the property was great overall. Very good experience with Royal Kona Resort and the area that it is in."
The price is CA $266
CA $354 total
includes taxes & fees
Jun 1 - Jun 2
Royal Kona Resort
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 Kaupulehu. 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 Kaupulehu?

Yes, you can find vacation rentals near the most popular sights in Kaupulehu, or you can go with a secluded option if you're looking for a relaxing stay. Discover why Kaupulehu is known for its spas and beaches. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation home rentals that Kaupulehu has to offer?

Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.: This vacation home near Kaupulehu is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Kaupulehu?

Expedia has 44 vacation rentals for your stay in Kaupulehu.

What’s there to see and do in Kaupulehu?

Kailua-Kona Beaches and Manini'owali Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Four Seasons Resort Hualalai Golf Course and Kua Bay are other places worth a visit.

What’s a vacation rental in Kaupulehu like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Kaupulehu. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

Recent reviews of Kaupulehu properties
Expedia verified reviews