Discover a selection of 2,000 vacation rentals in Historic Kailua Village, Kailua-Kona 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 air conditioning. Prices start at $96 per night, and houses and condos are popular options for a stay in Historic Kailua Village. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Historic Kailua Village
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Destination guide

Take in the waterfront beauty of Historic Kailua Village

The island views and other outdoor surroundings create an inviting atmosphere in Historic Kailua Village. Travelers to this walkable city praise the snorkeling, shopping and restaurants. If you're looking for accommodations with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Things to do

Activities and attractions in and around Historic Kailua Village

Are you hoping to find top things to see and do in the city? You'll be sure to enjoy Historic Kailua Village for its snorkeling and jogging trails. Venture out of your vacation home and check out everything that makes Historic Kailua Village a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Kona Le'a Plantation (4.2 mi / 6.8 km)
  • Kona Country Club (5.8 mi / 9.3 km)
  • Four Seasons Resort Hualalai Golf Course (12.9 mi / 20.8 km)
  • Makani Golf Club (15.7 mi / 25.3 km)
  • Kona Community Aquatic Center (0.7 mi / 1.1 km)
  • UCC Hawaii Kona Coffee Estate (2.6 mi / 4.1 km)
Weather

Seasonal weather averages in Historic Kailua Village

Travelers speak highly of Historic Kailua Village for its snorkeling. If you're planning a vacation around the weather, September, October, August and July are the hottest months to visit, when temperatures average 78°F.

Natural features

Exploring the beaches and other natural features in Historic Kailua Village

Historic Kailua Village is famous for its island views, breathtaking sunsets and tropical locale. Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Historic Kailua Village. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Mauna Kea Summit (0.5 mi / 0.8 km)
  • Old Kona Airport State Recreation Area (0.7 mi / 1.1 km)
  • Magic Sands Beach (3.4 mi / 5.5 km)
  • Kaloko-Honokohau National Historical Park (3.7 mi / 5.9 km)
  • Kahalu'u Beach Park (4.5 mi / 7.2 km)
  • Keauhou Bay Beach (5.7 mi / 9.2 km)
How to get there

How to get to and around Historic Kailua Village

The nearest airport is in Kona Intl. Airport (KOA), located 7.4 mi (11.8 km) from the city center.

What are the top vacation rentals in or near Historic Kailua Village?

Whether you're searching for an intimate retreat for you and your sweetie or a sprawling house to fit family and friends, you'll find some top vacation rentals in and around Historic Kailua Village. Here are a couple to get you thinking:

  • Take advantage of conveniences like a toaster and a coffee grinder at "Stunning, Romantic Cottage On Slope Of Hualalai". Located around 4 miles from Historic Kailua Village, this unique property has 1 bedroom and good guest reviews.
  • Another excellent choice is "Absolute Hawaiian Luxury Private 5 Acres Stunning Views Sunsets Wood Pizza Oven", which is around 6 miles from Historic Kailua Village. Featuring 4 bedrooms, an ice maker and a nearby hospital, it has everything you need to make your visit comfortable.

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

What are the best tiny house vacation rentals in or near Historic Kailua Village?

Punching above its weight when it comes to character, a tiny house vacation rental in Historic Kailua Village delivers big adventure. Shut down your gadgets and turn your focus to outdoor fun at one of these fun-sized stays:

  • Enjoy a simpler way of life at "Red Hawaii Tiny House". Amenities at this small wonder in Pacific States include a microwave oven, cookware, dishware and utensils and more.
  • "Green Hawaii Tiny House" in North Kona is another top-rated option. Heating and a kitchen will make your time here even more comfortable.

What are the top-rated vacation rentals for weekend getaways in or near Historic Kailua Village?

If you've been busier than a hamster on a treadwheel, you deserve to escape for a couple of glorious days. Leave work early on Friday and live it up at one of these weekend getaways in or near Historic Kailua Village:

  • "Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home" is around 1 mile west of Historic Kailua Village and an ideal place to recharge your batteries. You'll enjoy the amenities here, including a restaurant dining guide and beach sun loungers.
  • Otherwise, make new memories with your crew at "5 Star Luxury Oceanfront Beach Home", which is around 2 miles to the south of Historic Kailua Village. You'll have use of housekeeping services, a nearby marina and more here.

Can I find studio apartments for rent in and around Historic Kailua Village?

Studio apartments are a simple yet stylish option, ideally suited for traveling sweethearts or solo stays. Spend your days exploring the area and your nights kicking back in your comfy hideaway. These vacation properties in or near Historic Kailua Village are guaranteed to please:

  • Escape on your own or take a friend along to "Stunning, Romantic Cottage On Slope Of Hualalai". You'll have loads of amenities at your disposal, including a nearby laundromat and a washing machine.
  • Another fantastic choice is "Kona Reef - Oceanfront. . . See And Hear The Ocean Waves". Don't be fooled by its modest size — this cozy apartment is packed with convenient amenities like a nearby beach, internet services and plenty more.

Can I find short term rentals in or near Historic Kailua Village?

Whether you're searching for a studio apartment for you and a pal or a villa that'll fit the family, short-term rentals are easy to find in and around Historic Kailua Village. These properties are an ideal base for a whirlwind visit:

  • If you only need to stay a couple of nights, "Kona Reef - Oceanfront. . . See And Hear The Ocean Waves" is a fantastic choice. It's close to the center of Historic Kailua Village, so you'll be near all the best attractions.
  • Another excellent option is "New Kitchen/bath Remodel - Ocean Front". Round up your nearest and dearest and enjoy a comfortable stay near the heart of Historic Kailua Village.

What are the best romantic weekend getaways in or near Historic Kailua Village?

Forget about roses and chocolates. Sometimes all you need is to escape for a weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Historic Kailua Village that would make Cupid green with envy. Here are some we think you'll fall in love with:

  • Sneak away on Friday afternoon for a few passionate nights at "Stunning, Romantic Cottage On Slope Of Hualalai". Around 4 miles from Historic Kailua Village, it comes with lots of nice touches, including a nearby bay and a nearby marina.
  • "Absolute Hawaiian Luxury Private 5 Acres Stunning Views Sunsets Wood Pizza Oven" is another popular option that's bound to impress. It's about 6 miles from Historic Kailua Village and comes with beauty services and air conditioning.

What are the best large group vacation rentals in or near Historic Kailua Village?

Share your vacation and have more fun. Whether you're organizing an adventurous getaway with your besties or a family reunion, you'll have your pick of large group vacation rentals in and around Historic Kailua Village:

  • Offering comfort, space and privacy, you'll get your guests' stamp of approval at "Sky Villa Estate - Luxury Gated Retreat With Amazing Ocean View". Up to 14 people can stay at this retreat which has 5 bedrooms, a swimming pool and a fireplace. You'll discover it around 2 miles to the east of Historic Kailua Village.
  • Invite as many as 12 of your favorite folks to "Luxury Elegant Oceanfront Gated Estate" and fill the place with love and laughter. This popular option has 5 bedrooms and is around 3 miles to the south of central Historic Kailua Village. It's packed with features to keep your large group comfortable and content, including a swimming pool and mountain views.

What are the best houses for rent with a pool in or near Historic Kailua Village?

Of all the amenities a vacation rental can have, a pool is one of the most coveted. Browse these houses for rent with a pool in or near Historic Kailua Village and spend your time splashing about. Just remember to bring your inflatable doughnut:

  • Treat the gang to a memorable break at "The Onion House "architecture So Full Of Life It Seems To Breathe". There's plenty to love about this getaway besides its pool, such as towels and childrens activities.
  • "Independent Private House, With A Cellar Master" is the sort of place you go to escape the everyday and enjoy your surroundings, starting with its glorious pool. A living room and a kitchen are also on hand to make your visit as comfortable as possible.

Not sure how to pack for your Historic Kailua Village break? This enticing destination has an oceanic climate. In the summertime, you can expect average temperatures of between 75 ºF and 80 ºF. Look up our range of Historic Kailua Village vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Historic Kailua Village?

You'll always have more fun sharing the good times with the folks you love the most. Whether you're planning a family break or getting away with friends, Vrbo has a large vacation rental to suit your needs. These are two of our best in and around Historic Kailua Village:

  • Sleeping up to 10 guests in 4 bedrooms, "Absolute Hawaiian Luxury Private 5 Acres Stunning Views Sunsets Wood Pizza Oven" is the ideal place to spend quality time with the family. This popular retreat is 6 miles to the southeast of Historic Kailua Village and has amenities that include a garden and a dining table.
  • "Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home" also has the space you need to connect with the ones you love. This rental is around 1 mile to the west of central Historic Kailua Village and accommodates 8 guests in its 4 bedrooms. A travel crib and books will help keep everyone comfortable and happy.

If you'd love to do some sightseeing, there are plenty of family-friendly attractions nearby to add to your to-do list. Mauna Kea Summit, Kailua Pier and Kona Community Aquatic Center are fine places to start.

Can I find family cabin rentals in or near Historic Kailua Village?

Cozy up with the kids in a family cabin rental in or near Historic Kailua Village and get ready to make some lovely new memories together. Here are a couple of favorites:

  • "Kaloko Mountain Cabin Above Kona With Hot Tub And Fireplace" - This popular escape offers a microwave oven and a DVD player and is located approximately 6 miles northeast of central Historic Kailua Village.
  • "Granma's Cabin Kona Coast" - Rally the troops and spend a few days or more at this inviting property, which is around 6 miles to the north of Historic Kailua Village. You'll have access to free toiletries, nearby birdwatching activities and a good deal more.

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