Discover a selection of 27 vacation rentals in Kailua-Kona, HI, US 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 pool and internet/wifi. Prices start at C$ 155 per night, and house rentals and condo and apartment rentals are popular options for a stay in Kailua-Kona. Either way, you'll find a rental for everyone's needs.

What are the top vacation rentals in or near Kailua-Kona?

Elegant mansions, tranquil houseboats and sprawling homes — everyone's ideal escape is different. Whatever your style, you're sure to find something you love among these top vacation rentals in Kailua-Kona:

  • "Stunning, Romantic Cottage On Slope Of Hualalai": If you're after a comfy living space in Kalaoa, this rental won't disappoint. It offers 1 bedroom and great amenities including a kitchenette and a dining table.
  • "Absolute Hawaiian Luxury Private 5 Acres Stunning Views Sunsets Wood Pizza Oven": Stay a few nights or more at this property in Keauhou and you'll have access to games, an ocean view and more. It has 4 bedrooms to accommodate your friends and family.

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

What are the best tiny house vacation rentals in or near Kailua-Kona?

You need only step foot inside one of our tiny house vacation rentals in Kailua-Kona to discover that good things really do come in small packages. Designed to maximize every spare inch of space, these mini wonders promise a big vacation experience:

  • Experience a simpler way of life at "Red Hawaii Tiny House". Amenities at this small wonder in Pacific States include a firepit, a garden and more.
  • "Green Hawaii Tiny House" in North Kona is another superb option. A barbecue grill and a garden will make your time here extra comfortable.

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

If you've been busier than an ant at a picnic lately, you deserve to escape for a few blissful days. Skip out of work early on Friday and head for one of these weekend getaways in or near Kailua-Kona:

  • Put your feet up at "Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home". Located about 19 kilometers to the southwest of Kailua-Kona, it has all you need for a chilled out stay, including winery tours and a pool.
  • Alternatively, live it up with loved ones at "5 Star Luxury Oceanfront Beach Home", which is around 19 kilometers to the southwest of Kailua-Kona. You'll have use of water sports equipment, cable/satellite TV services and more here.

Can I find studio apartments for rent in and around Kailua-Kona?

Studio apartments may be small in size, but they pack a mighty punch when it comes to location and convenience. Make yourself comfortable at one of these popular studio apartments in or near Kailua-Kona:

  • After a fun-filled day of outdoor exploration, relax in total comfort at "Stunning, Romantic Cottage On Slope Of Hualalai". Nearby ecotour services and a fridge are among the amenities you'll find here.
  • An equally fantastic rental is "Kona Reef - Oceanfront. . . See And Hear The Ocean Waves". Don't be fooled by its compact size — this comfy apartment is packed with useful amenities like a water view, towels and lots more.

Can I find short term rentals in or near Kailua-Kona?

From simple studio apartments to large vacation homes, Vrbo has your quick escape sorted. Here are two of our most popular stays in and around Kailua-Kona:

  • If you can only spare a few nights, "Kona Reef - Oceanfront. . . See And Hear The Ocean Waves" has you covered. It's not too far from the center of Kailua-Kona, so you'll have easy access to all the top attractions.
  • Another great choice is "New Kitchen/bath Remodel - Ocean Front". Round up your nearest and dearest and enjoy a relaxing stay close to the heart of Kailua-Kona.

What are the best romantic weekend getaways in or near Kailua-Kona?

Forget chocolates and flowers. Sometimes all you need is a weekend away, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Kailua-Kona that would make even Cupid envious. Here are some we think you'll fall in love with:

  • Located around 11 kilometers from Kailua-Kona, "Stunning, Romantic Cottage On Slope Of Hualalai" is an ideal place for doting lovebirds. A nearby bay and a dining table are among the many amenities here.
  • Otherwise, spend your break drinking wine and canoodling at "Absolute Hawaiian Luxury Private 5 Acres Stunning Views Sunsets Wood Pizza Oven", around 23 kilometers from Kailua-Kona. Beauty services and outdoor furniture will help set the mood.

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

About 13 kilometers to the west of Kailua-Kona, Kona Palisades is an awesome spot to rent a vacation home for a weekend. Spend Saturday sightseeing in the local area and then Sunday doing whatever your heart desires! Alii Heights Mauka is another favorite place for a weekend visit. It's located 21 kilometers southwest of Kailua-Kona.

What are the best large group vacation rentals in or near Kailua-Kona?

Share your vacation and multiply the fun. Whether you're planning an epic escape with your best friends for a family get-together, you'll have your choice of large group vacation rentals in and near Kailua-Kona:

  • A wealth of amenities including a swimming pool and a garden make "Luxury Estate With Huge Pool And Hot Tub" a top pick for groups. This getaway has 5 bedrooms and sleeps up to 15 people. From the center of Kailua-Kona, it's around 11 kilometers away to the southwest.
  • Invite as many as 14 of your friends to "Sky Villa Estate - Luxury Gated Retreat With Amazing Ocean View" and fill the place with love and laughter. This option has 5 bedrooms and is around 16 kilometers to the southwest of central Kailua-Kona. It's crammed with features to keep a large group happy and comfortable, such as a fireplace and a beach view.

Are there large vacation rentals that sleep 30 or more in or near Kailua-Kona?

Go on and plan that fancy shindig. We've got large vacation rentals in and around Kailua-Kona that offer plenty of space to live it up with loved ones. Rally the troops and head for one of these retreats:

  • "When You Want To Be Close - But Not Too Close": Sleeping up to 30 guests, there's enough room to make everyone feel comfortable. Make the most of amenities including a firepit and a garden.
  • "New Oceanfront Kona Studio With Pool Access + Bbq": Make yourselves right at home with top amenities like a kitchen and a nearby bay. This spacious retreat sleeps up to 100 guests.

What are the best houses for rent with a pool in or near Kailua-Kona?

Nothing screams fun and frivolity like a pool does. Pump up your unicorn floatie and browse these rental houses in or near Kailua-Kona that feature this vacation necessity:

  • Say hello to "The Onion House "architecture So Full Of Life It Seems To Breathe", where your main priority will be relaxing by the pool. Amenities including outdoor furniture and a barbecue grill help make this retreat a favorite with guests.
  • "Independent Private House, With A Cellar Master" is the sort of place you go to get away from it all and enjoy your surroundings, starting with its pool. Towels and a swimming pool are also on hand to make your stay as comfortable as possible.

Not sure how to pack your bags for your Kailua-Kona getaway? This leading destination has an oceanic climate. In the summertime, expect average temperatures of between 75null and 80null. Check out our selection of Kailua-Kona 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.