Kailua-Kona Vacation Rentals

Paradise awaits you when you book your home-away-from-home in Kailua-Kona.

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Visit Kailua-Kona

Nestled in between North and South Kona sits Kailua-Kona, a white-sand beach paradise perfect as its own destination or home base for exploring the Kona Coast. Aliʻi Drive’s eateries serve up the ocean’s catch-of-the-day and give you ample chance to fill your shopping bags. Golfers flock to Kailua-Kona’s course and maybe the paradise views even up their games. The volcanoes, white-sand beaches, and lush landscape draw people to the Kona Coast for good reason and once you savor the vibes, waters, and of course the perfect cup of Kona coffee, odds are this won’t be your last visit to this Hawai‘i shining star. 

Your Kailua-Kona Vacation, Your Way.

Find Your Kailua-Kona Rental

New Property

Kailua-Kona, HI

2 Bdrms 1.75 Baths 4 Guests
From $200.00
per night + taxes & fees
Featured Property

Kailua Kona, HI

3 Bdrms 3.5 Baths 6 Guests
From $375.00
per night + taxes & fees
Featured Property

Waikoloa Village, HI

3 Bdrms 2 Baths 6 Guests
From $200.00
per night + taxes & fees
Featured Property

Kailua Kona, HI

3 Bdrms 2 Baths 6 Guests
From $184.00
per night + taxes & fees
New Property
Featured Property

Waimea, HI

3 Bdrms 3.5 Baths 6 Guests
From $736.00
per night + taxes & fees

Featured Kailua-Kona
Vacation Rentals

Your Local Team

Locally Owned and Operated In Kailua-Kona

Remember, when you rent with SkyRun, you can expect superior, prompt, and personalized service.

  • Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly.
  • Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay. 
  • Our property manager are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation.

Meet Rich and Toni, full-time residents of West Hawai‘i for the past 15 years. They are excited to help you plan the perfect getaway to the beautiful Kailua-Kona, HI.

Rich & Toni White

Kailua-Kona, HI

Owners

Let's Talk!

Mahai’ula Beach (Red House Beach)

Spy the red house that gives this beach its nickname and enjoy sitting under the shade of trees that beckon you to take a break from the Hawaiian sun. Getting there requires a short walk or high-clearance vehicle, but this keeps the crowds at bay. Pack everything you need, since there are no amenities at this natural beauty. 

Kikaua Point Park (Keiki Beach)

Keiki Beach means “children’s beach”,  so you can guess that families love this locale for its manmade lagoon that’s ideal for the little ones to splash around. The adjacent grassy area invites you to spread a blanket and enjoy a surfside picnic. 

Kekaha Kai State Park

Head to the North Kona Coast and explore three distinct parts of the park. Maniniʻowali Bay (Kua Bay)’s calm waters invite a day of swimming and play. Makalawena Beach dazzles with black sand—remnants of volcanoes past but this area’s currents make swimming too challenging. A little farther out sits Mahaiʻula Bay, ideal for trekking along the sandy dunes. In addition to fabulous snorkeling, be sure to visit the petroglyph fields and ponds full of tropical fish. 

Hōnaunau Bay

Housing the Puʻuhonua o Hōnaunau National Historical Park, this Kona area overflows with Hawai‘ian culture. The park’s history as the spot where lawbreakers of the past flocked for refuge infuses its 180 acres. 

Hiking

Put on  your hiking boots for Makau’ula O’oma Trail’s moderate 4.5 mile course that  hugs the Hualālai volcano. Ascend 2,000 feet and feast on the views of  Mauna Loa, Mauna Kea,and Hualālai when you reach the pinnacle of Pu’u Wa’awa’a Cinder Cone Trail. Hike these trails and more and let the Kailua-Kona flora, fauna, water, and sky cast their spells upon you. 

Fishing

Will you be the next fisherman to catch a record-breaking marlin? It’s possible when you fish along the Kona Coast. In fact, this stretch has netted people marlin clocking in at more than 1,000 pounds. Fishing charters can take you to the hottest spots where tuna, mahi mahi, ono, sailfish, and, of course, marlin, bite. Inshore fishing can net you smaller catches like mackerel and papio and might be a better choice for your little fisherman. For an even lower key outing, cast your line from the beach and see what’s biting!

Golfing

Tee off in paradise at one of Kona Coast’s public or private courses. Kona Country Club and Kukio Golf Club both offer lush views, challenging courses, and plenty of time to perfect your game against a paradise backdrop. Head to North Kona’s Makalei Golf Club where native plants, lava tubes, and native plants make this a very Hawai‘in golfing experience. 

Arts & Culture

Kona Coast’s natural beauty is rivaled only by its historical and cultural connections to Hawai‘in culture. Visit Hulihe’e Palace and walk into a site dedicated to preserving Hawai‘in history and language. The “Westminster Abbey of the Pacific”, Maku’aikaua Church is the first Christian church built on the island. Take a guided tour of Ahu’ena Heiau, a  heiau, or sacred temple, constructed to honor Lono, the god of prosperity and fertility. And you might not be on the run from the law, but those rebels who broke the law of the kapu only had two choices: death or flee to Pu’uhonua o Honuaunau. Pu’uhonua o Honuaunau National Historical Park (aka Place of Refuge) might not offer legal sanctuary but does offer visitors films screenings detailing the site’s history and tours as well as offering a natural refuge to all who visit. 

Lūʻau

Don’t let your Kona Coast stay pass without basking in this Polynesia celebration of food, culture, music, and dance. The first lūʻau dates from around 1819 and the celebration continues today with poi, poke, and laulau. Multiple lūʻau happen in Kona, so don your leis and bring your appetites to take part in this cultural feast. 

Water Adventures

Surfing, snorkeling scuba diving, and parasailing. Do it all when you stay along the Kona Coast. Fly high above the turquoise waters and gaze on lush mountains and volcanic fields when you parasail above the water. Some Kona picks for snorkeling that brings you close to the ocean’s world include Kealakekua Bay, Kahaluʻu Beach Park, and Puʻuhonua o Honaunau National Historical Park. Manta rays and coral reefs greet you when you dive into the Pacific. Check out scuba tours, including day dives, night dives, and guided dives to take you to the perfect underwater spot.

Tours

Taste your way along the Kona Coast with a tour of  a chocolate farm or coffee farm–after all, this is where Kona coffee hails from. Maybe you want to explore more of the waters with a manta ray boat tour and watch these fish meet to feast at night. If a 360-degree view is a must, helicopter tours take you up and take your breath away. Too adventurous? Take to the waters for a whale watching excursion. Book one of all of these excursions for the ultimate Hawaiian experience. 

Biking

Take a gentle ride along the coast and let the salt air ride with you, waves providing the only soundtrack you’ll want. Maybe you choose to explore the forest trails and discover the lushness of the plants on the forest floor. Amp it up with ascents along Hualalai Road and Waipio Valley’s switchbacks and terrain that leaves you breathless. 

Surfing

If you’re a seasoned wave rider or dipping your toes in the surfing pool for the first time, the Kona Coast serves up some of the world’s premier areas. North of Kona Airport sits Kohanaiki Beach, a spot well-suited for intermediate and advanced riders. Newbies might want to check out Kahaluʻu Beach in Keauhou. Kohanaiki Beach Park’s waves offer tons of practice to hone your wave riding skills. 

Aliʻi Drive

Make time to dine, shop, and explore Aliʻi Drive,  Kailua-Kona’s hub for retail, bars, and dining. Of course Kona coffee dots the menu, and sipping that first-morning cup or cooling off with an icy afternoon blend oceanside might just be the best java experience you’ll ever have. Cap it off with art from one of the galleries lining the area and take a little piece of the Kona Coast home.

What To Expect

Get that “home away from home” feel while enjoying the streamlined, convenient guest experience that includes full attention to every detail.

During your stay, you can expect SkyRun staff to be close by and available to help you make the most of your trip. You can reach them via web chat, email, text, or phone. They’re available and accessible daily, and on-call 24/7 for emergencies.

What’s included
Independent homeowners contract with SkyRun Vacation Rentals to professionally manage their properties and create stellar vacation experiences for their guests.

Every SkyRun property is unique, so certain features and amenities are variable. To ensure you’re selecting the right property for your needs, review the photos and note the amenities listed for the property. Read the sections called “What you’ll love” and “What to be aware of” at the bottom of each listing, and check out reviews from prior guests.

Included Services:

  • Full cleaning prior to your arrival
  • Pre-arrival inspection
  • Wi-Fi and TVs
  • Most properties have free parking (check each property for possible charges)
  • Luxury linens and towels
  • Fully stocked kitchen
  • Cleaning and trash removal upon departure

Included Amenities and Starter Supplies:

  • Coffee and coffee filters (if applicable)
  • Salt and pepper
  • Soap/shampoo/lotion
  • Toilet paper
  • Paper towels
  • Hair dryer
  • Ironing board
  • Dish soap and dishwasher detergent (if applicable)
  • Laundry detergent (if applicable)
  • Alarm clock
  • Firewood (if applicable)

Additional Services:

  • Crib or toddler bed with sheet: $10/day
  • Pump-up bed with sheets: $10/day
  • Mid-stay cleaning service: Ask your local SkyRun staff for pricing
  • Grocery delivery: Cost of groceries +10% + $20/hr
  • Travel insurance: 7% of your stay

Property Damage Waiver

SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure.  It does not cover damage that is willful, the result of negligence, or damage caused by the misuse of household items.  It also doesn’t cover unreported damage.  SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is nonrefundable.

If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file.  Coverage is provided to you and all traveling companions that are staying in the home overnight during your stay.

Coverage is not provided for loss due to:

  • Your intentional acts or gross negligence.
  • Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party).
  • Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
  • Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report.

Your Duties in the Event of Damage. You must:

  • Take all reasonable, necessary steps to protect the property and prevent further damage to it.
  • Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
  • Provide us documentation such as pictures to substantiate the claim.

Travel Insurance

Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more.

Group coverage protects everyone in your traveling party for one low price.

Get a quote.

Check-In Instructions

Check-In:

  • Check-in is 4:00 p.m. HST. 
  • Seven days prior to the arrival date, guests will receive an email that contains directions and access information for the property. 
  • In most cases, guests will access a property via a lockbox or smart lock using an access code. 
  • Early check-ins can be confirmed only on the day of arrival.

 

Check-Out:

  • Check-out is 10:00 a.m. HST.  
  • Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. 
  • Late check-outs must be coordinated directly with the SkyRun office no later than 9 a.m. on the day of departure. Please note that if we have an incoming guest we will not be able to accommodate a late checkout.  
  • We ask that guests remove major trash from the unit, return the furniture to its original location, and load and run the dishwasher.

 

Parking:

  • The check-in instructions email will contain information regarding parking at your property.   
  • Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us.  Parking fines can be significant.

Property Management You Can Trust

Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions.

Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties.

Learn More

“My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.”

 

Kay JohnsonDestin, FL

SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them.

Nan S.Sarasota, FL

The entire process has been incredibly smooth, providing us with a true sense of peace of mind. From property management to timely payments, it’s been hassle-free. We couldn’t be happier with the service provided by SkyRun.

Melissa TaylorW. Bradenton, FL

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Kailua-Kona Frequently Asked Questions

SkyRun provides photos, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions.

Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials.  We sweat the details and provide starter supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc.  We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions.

When you book direct with SkyRun you avoid paying service fees that traditional listing channels charge, like Airbnb. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. SkyRun can help you plan and save on your entire vacation experience, not only the rental itself.

Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you book with a 3rd party booking site. You may also add travel insurance to your reservation within 48 hours of booking. The cost of travel insurance varies and is usually between 7%-9.5% of your total reservation cost, depending on the coverage type.  If you do not have travel insurance, you cannot cancel your reservation for any reason.  If you have travel insurance and need to cancel or make a claim, refer to your specific policy.

You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner.  When you book, 1/3 of your total reservation cost, or a minimum of $300, is charged as a non-refundable deposit to secure your rental. Thirty days before your arrival, the remaining amount is due. At this time, the credit card we have on file will be automatically charged for the balance. You may cancel for a full, no-questions-asked refund up to 14 days before your arrival. After that, your payment becomes non-refundable. (See travel insurance above for exceptions).

For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if any questions arise.

No smoking and no pets (unless specifically designated as a pet-friendly property) are allowed in the rentals.  House parties and exceeding the maximum occupancy at any time are prohibited. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves.

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