Discover a selection of 1,000 vacation rentals in Kaupulehu that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $835 per night, and houses and villas are popular options for a stay in Kaupulehu. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Kaupulehu
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What are the top vacation rentals in or near Kaupulehu?

From upmarket condos to inexpensive cottages, Vrbo has properties to match every taste and budget. Pack your bags and check out these top vacation rentals in Kaupulehu:

  • Luxury Oceanview Villa At Hualalai W: If you're searching for somewhere in North Kona with 2 bedrooms and plenty of charm, this escape will tick your boxes. Amenities include a chef and a stovetop.
  • Luxury Coastal View Villa At Hualalai W: Located in North Kona, this home away from home has 3 bedrooms and lots of handy amenities. Shopping and a garage are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Kaupulehu vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Kaupulehu?

Get far away from the busyness of everyday life at one of our weekend getaways in or near Kaupulehu. Whether you want to hang out with friends or spend valued time with the fam, we'll have something to suit your style. Here are a few places we think you'll love:

  • New Kitchen/bath Remodel - Ocean Front is perfect for a few days of enjoyment and rest. It offers a host of amenities, such as off-street parking options and a beach view, and is located 14 miles to the south of Kaupulehu.
  • Alternatively, pack a few clothes into your bag and enjoy a mini break at Oceanfront Poolspa Private 4 Bedroom Home Walk To Town Christmas Open. This well-liked getaway is about 13 miles south of Kaupulehu and comes with tennis and a porch.

What are the best romantic weekend getaways in or near Kaupulehu?

Forget chocolates and roses. Sometimes all you need is to take off for the weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Kaupulehu that would make Cupid swoon. Here are some we think you'll be enamored with:

  • Sneak off on Friday for a few passion-filled nights at 5 Star Luxury Oceanfront Beach Home. Roughly 14 miles from Kaupulehu, it comes with lots of nice touches, including spa and beauty services and a beach.
  • Kona Reef - Oceanfront. . . See And Hear The Ocean Waves is another top option that'll impress. It's about 13 miles from Kaupulehu and comes with an ocean view and golf.

What's the best place to stay if you're looking to rent a house for a weekend in or near Kaupulehu?

A long weekend of crisp, clean sea air and carefree vibes at Magic Sands Beach in Kahaluu Bay will work wonders. Book a rental home and stay a couple of nights at this attractive coastal destination located 16 miles to the south of Kaupulehu.

What are the best large group vacation rentals in or near Kaupulehu?

Share your trip and have more fun. Whether you're planning an epic getaway with your best friends or a big family get-together, you'll have your choice of large group vacation rentals in and around Kaupulehu:

  • Providing comfort, space and privacy, you'll get your guests' stamp of approval at Luxury Elegant Oceanfront Gated Estate. Up to 12 people can be accommodated at this property which has 5 bedrooms, a washing machine and a nearby marina. This group favorite is around 15 miles to the south of Kaupulehu.
  • Nothing is more important than spending time with the people you love, and Kona Dream 3 Spacious Units, 2 Pools is the ideal place to do that. Located around 18 miles to the south of Kaupulehu, as many as 12 guests can stay in this vacation rental which has 3 bedrooms. An iron and ironing board and internet services are among the numerous amenities here.

What are the best houses for rent with a pool in or near Kaupulehu?

Nothing screams fun like a pool does. Grab your inflatable swan and browse these houses in or near Kaupulehu that come with this vacation perk:

  • Pack your swimsuit and book a few days or more at The Onion House "architecture So Full Of Life It Seems To Breathe. There are also lots of other great amenities here, including a barbecue grill and a stovetop.
  • Kona Sunset House" On Walua: Breathtaking Ocean Views With Incredible Pool is the type of place you go to escape from it all and enjoy your surroundings, starting with its inviting pool. WiFi and a free nearby fitness center are also on hand to make your stay nice and comfy.

Kaupulehu has an oceanic climate, with average summertime temperatures fluctuating between 75 ºF and 80 ºF. But there's no need to wait until summer to visit! Take a look at the search bar at the top of the page and adjust the filters to find the ideal Kaupulehu vacation rental and organize your getaway for whatever season you like.

What are the best large family vacation rentals in or near Kaupulehu?

Whether your perfect escape is out in the countryside or by the ocean, you'll enjoy it even more if you share it with people you love. Check out these large family vacation rentals in or near Kaupulehu and bring the whole gang:

  • Around 14 miles to the south of Kaupulehu, 5 Star Luxury Oceanfront Beach Home has 4 bedrooms and fits up to 8 guests. It's equipped with a range of amenities, including beach towels and a free nearby fitness center.
  • Oceanfront Poolspa Private 4 Bedroom Home Walk To Town Christmas Open is also popular with families. It's around 13 miles to the south of Kaupulehu, has 4 bedrooms and accommodates up to 10 people. Handy amenities here include a restaurant dining guide and a beach view.

When you're ready to get out and explore, there are lots of family-friendly attractions in the area to keep everyone happy and entertained. Mauna Kea Summit, Kailua Pier and Kona Community Aquatic Center should be top of your to-do list.

Can I find family cabin rentals in or near Kaupulehu?

Escape the hustle and bustle and treat the people you love to a different kind of vacation. Stay in one of these family cabins in or near Kaupulehu and get the camping experience — but with all the comforts of home!

  • Kaloko Mountain Cabin Above Kona With Hot Tub And Fireplace - Enjoy quality time with your gang at this getaway, which is around 7 miles south of central Kaupulehu. A wood stove and water sports equipment are among its family-friendly amenities.
  • Hawaii Bamboo Grove Cabin - Another awesome choice, this cabin comes with a kitchenette, cookware, dishware and utensils and more. You'll find it around 20 miles to the south of Kaupulehu.

For more options, use the search bar at the top of the page and adjust the filters to find the Kaupulehu vacation rental that's perfect for your needs.

Can I find two-bedroom vacation rentals in or near Kaupulehu?

It's easy to plan a wonderful getaway with Vrbo. Whether you prefer a comfy cottage or a modern apartment, you'll find great two-bedroom options in or near Kaupulehu: Here are just some of our faves:

  • Leading our list is Luxury Oceanview Villa At Hualalai W. This two-bedroom beauty has handy amenities like a stovetop and an iron and ironing board. Explore Kaupulehu's excellent attractions from this comfortable pad.
  • Another popular option is Four Seasons Luxury Ocean View Hainoa Villa 2905b. With useful amenities such as an iron and ironing board and outdoor furniture, you'll have no trouble making yourselves at home here. Choose your rooms, unpack your bags and let the fun begin!

What are the best three-bedroom vacation rentals in or near Kaupulehu?

Three-bedroom rentals in or near Kaupulehu give you both space and flexibility to make the most out of your vacation. Take a look at some of the options available here:

  • Offering the trifecta of comfort, space and privacy, you'll get your entire gang's nod of approval at Luxury Coastal View Villa At Hualalai W. This retreat comes with amenities including a garage and a TV.
  • Alternatively, check out the spacious vacation rental that is Hualalai Ke Alaula 217a - Split Level Luxury Villa W. Stretch out with your loved ones and make the most of its many conveniences, such as a fridge and a washing machine.