Vacation rentals with a kayak in Kailua-Kona

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Top-rated kayak rentals in Kailua-Kona

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Guest favorite

A spacious lounge area features a light grey sectional couch adorned with several white pillows. Large windows frame stunning ocean views, offering a bright and airy atmosphere. A small wooden coffee table sits at the center, complemented by a decorative bowl.

Condo in Waikoloa Village

4.9 out of 5 average rating, 40 reviews

NEW Sweeping Ocean View Retreat/Golf/Pool/PB Court

Hale Kai II Penthouse-unparalleled ocean views, offering a sense of serenity and luxury that is unmatched! This unforgettable escape, is the place where ocean gazing memories are made. Take in a spectacular sunset or enjoy a read on the oversized lounge couch. Embrace the charm of this vibrant community, where you can indulge in a round of golf, enjoy fresh seafood, explore local beaches, and relax in this 1br + open loft br,2 full bathroom villa... a very spacious penthouse w gourmet kitchen.

Top guest favorite

A lush green yard is framed by palm trees, with vibrant blue water visible beyond. A pathway of stepping stones leads through the manicured grass towards the ocean, highlighted by a clear sky dotted with scattered clouds.

Home in Keauhou

4.99 out of 5 average rating, 74 reviews

The Mango Cottage on Keauhou Bay

Cottage on private, gated, 1 acre waterfront estate. Swim, surf, kayak, and snorkel from yard. Watch dolphins and boats in the bay. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. King bed. Living room. Full kitchen. Bathroom with large shower. Covered deck with partial ocean views. Use of kayaks and stand-up paddle boards. Book alone or with Ocean Cottage. Couples and single travellers only.

Guest favorite

A cozy sleeping area features a spacious bed adorned with a floral-patterned blanket in blue and yellow. Windows allow natural light, and a television is mounted on the wall. A decorative shelf holds towels, contributing to the room's functionality.

Guest suite in Kailua-Kona

4.9 out of 5 average rating, 286 reviews

Jasmine Studio; No Cleaning Fee. King Bed

Located conveniently 5 minutes from the airport and a short 15 min drive to downtown Kailua Kona. Vaulted ceilings, a cute lanai to enjoy your morning coffee, large bathroom with double vanity, and a kitchenette make this rental a real gem. The AC is powerful for when the tropical breeze isn't quite cool enough, The WIFI is reliable and there is a large screen TV with ROKU for when you just want to hang out. We offer automated check in, excellent room amenities and flexibility with booking.

Top guest favorite

The kitchen features warm wooden cabinetry and open shelving, complemented by modern appliances including a stainless-steel fridge and dishwasher. A round dining table is surrounded by light-colored chairs, while natural light floods the space through a wide window, enhancing its bright and functional design.

Home in Waikoloa Village

5 out of 5 average rating, 19 reviews

Waikoloa Treehouse 3 bed 2 bath

Aloha! 🌺 Relax with the whole family at this peaceful home in Waikoloa Village with many great nearby restaurants and shopping. Just 6 miles to world class beaches and resorts. Newly remodeled kitchen fully stocked with everything you need for your Hawaiian vacation. The home has been remodeled and landscaped with peek-a-boo ocean and sunset views from a huge backyard deck with a gas fire pit and BBQ. Community pool/tennis/pickleball access and ample beach gear, paddles/rackets included.

Top guest favorite

A spacious living area features large glass doors opening to a covered patio with outdoor seating. A comfortable sofa is complemented by a modern coffee table, while a television provides entertainment. Natural light fills the room, creating a connected indoor-outdoor environment.

Apartment in Waikoloa Village

5 out of 5 average rating, 13 reviews

Sweeping Views - Spacious 3 Bds!

This stylish place to stay is perfect for group trips. “Ho'ohano” is a Hawaiian word that can be used to describe something pleasing or enjoyable, and believe us when we say that it’s the perfect word for this stunning 3-bedroom on Hawaii’s Big Island! Located in the desirable Waikoloa Village, fine dining and shopping are very close as well as amazing on-site amenities of the pool, hot tub, shuffle board, spacious patio with chaise lounge seating, and a pavilion with barbeque grills.

Guest favorite

A spacious home is depicted against a lush green backdrop, featuring a large deck with a hot tub. The structure showcases multiple solar panels on the roof, white railings, and an elegant staircase leading to the ground level, surrounded by vibrant tropical foliage.

Home in Kailua-Kona

4.91 out of 5 average rating, 128 reviews

Kona Mountain Home, 3/2, lanai, hot tub, sleeps 8

My home is a classic Hawaiian ranchette on the slopes of Hualalai, on 3 acres of beautiful Hawaiian forest. It has beautiful lanais, a deck with hot tub downstairs, along with a workout room and ping pong table. KMH is close to several of Kona's beautiful beaches, the Big Island's most challenging golf, and has great views of the Kona coast. It is also adjacent to a Nature Preserve where you can hike for miles through the Forest. My home will make you feel like you live in Hawaii!

Top guest favorite

A modern kitchenette features a refrigerator, microwave, and a small stove. Natural light enters through the window, creating a bright atmosphere. A dining table is situated nearby, accompanied by four chairs. In the background, a cozy bedroom is visible, showcasing a spacious bed with colorful decorative accents.

Guesthouse in Captain Cook

4.98 out of 5 average rating, 118 reviews

Pebble Beach House- 2 Minute Walk to the Beach!

Come enjoy our guest house with Pebble Beach just a 2 minute walk down the road! Our piece of paradise is located in a peaceful neighborhood where you can see and hear whales spouting and slapping their tails (in season) and enjoy ocean sunsets. Pebble Beach is a great place to snorkel, kayak, or start a hike along the Kings Trail to volcanic formations or a hidden black sand beach. We are located approximately 45 minutes south of Kona, and 75 minutes to Volcanoes National Park.

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A covered patio area is furnished with comfortable seating and a wooden table, surrounded by lush tropical vegetation and vibrant flowers. Large glass doors lead into the interior space, while wooden pillars add a rustic charm to the entrance.

Home in Kawaihae

5 out of 5 average rating, 3 reviews

Spectacular Ocean View & Peace

Explore Peaceful Hale, where abundant quiet and serenity, incredible views, sunsets and night skies with rolling hills and lots of open space await you at our end-of-the-road location. Spectacular view from every room. Experience a very unique, rural feel while being only minutes away from world class beaches, excellent snorkeling, diving, surfing, hiking, along with numerous and varied restaurants and the most popular big island resorts. TAXES INCLUDED IN PRICE

Guest favorite

A nighttime view of the property features multiple buildings adorned with colorful lights, illuminating the outdoor space. A swimming pool reflects the vibrant lights, while lounge chairs are positioned nearby, inviting relaxation under the starlit sky.

Guest suite in Kailua-Kona

4.92 out of 5 average rating, 409 reviews

Kona Amazing Ocean Sunset

Charming, elegantly renovated Ohana in Kona Palisades. This unit has a tight modern feel with a local flair. Mahagonny trim flows throughout! Good for couples and honeymooners and families! Centrally Located in the heart of the Gold Coast of West Hawaii, 7-mile drive to downtown Kona and Kua Beach, less than 8 min from the airport. We are close to the Ocean, Rainforest, restaurants, and stores! We also have another studio unit on our property.

Top guest favorite

An aerial view showcases the spacious one-bedroom Ohana, surrounded by vibrant tropical gardens and landscaping. A shared pool is visible in the backyard, framed by lush greenery. Nearby homes and the peaceful neighborhood are also depicted in this inviting setting.

Guesthouse in Kailua-Kona

5 out of 5 average rating, 14 reviews

Aloha Kona Getaway | Pool | Laundry & Parking

Forget your worries in this spacious and serene one-bedroom Ohana perched above Al’li Drive. Immerse yourself in the beauty of our tropical paradise with lovely pool views, lush gardens, hammock, and inviting patios. Whether you’re here to work or play, our Ohana has everything you need for a perfect getaway. Our Ohana offers a comfortable and well-appointed king bedroom, areas for work, and equipped kitchenette.

Guest favorite

A spacious lanai features comfortable seating arrangements with soft cushions and a low coffee table. Lush tropical foliage surrounds the area, enhancing the serene ambiance. The outdoor space offers a view of well-maintained greenery, ideal for relaxation or outdoor dining.

Condo in Puako

5 out of 5 average rating, 6 reviews

Luxury Vacation Retreat at Mauna Lani Point J107

Discover paradise in this 2-bedroom, 2.5-bathroom end-unit condo in the prestigious Mauna Lani Point community. Enjoy breathtaking Mauna Kea views, lush tropical scenery, and exclusive access to the Mauna Lani Beach Club and complex amenities center—perfect for a luxurious Hawaiian getaway. INCLUDES ACCESS TO MAUNA LANI FITNESS CENTER - POOL,SPA, TENNIS, PICKLEBALL, WORKOUT ROOM AND CLASSES

Guest favorite

The exterior of the home is surrounded by lush greenery and colorful plants. A well-maintained driveway leads to a carport, with expansive windows allowing natural light to illuminate the front interior. Clouds add texture to the blue sky overhead.

Home in Kealakekua

4.92 out of 5 average rating, 72 reviews

One bedroom studio (private)

Our home is located in Kealakekua. It is located at 1.400 feet in elevation which provides cooler nights and relaxing rainy afternoons during the rainy season. Home was completely remodeled in winter of 2022. We are 5 min away from a few great dining options and the beautiful Kealakekua Bay known for its amazing snorkeling! Enjoy your own private space with a shower and toilet.

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Popular amenities for Kailua-Kona kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior view features a multi-level house surrounded by lush greenery. A private pool is set within a well-maintained lawn, complemented by patio chairs and a dining area. Large glass doors provide an inviting connection to the outdoor space.

Home in Keauhou

4.93 out of 5 average rating, 102 reviews

Amazing Place to Stay on Keauhou Bay! Pool/AC!

MikeRating, 5 stars3 weeks ago

Great space for my wife and I and our four adult children. Loved the ability to walk to bay to paddle board. Kona country club golf was 5 minutes away and a fantastic experience for me and my two sons. AC in the house worked extremely well. Pool was a popular afternoon spot. Wi-Fi was good and helped for the unfortunate times I had to log into work. Close to grocery store and restaurants. Overall a great home base for exploring the Big Island!

Guest favorite

The tri-level home is set against a clear blue sky, featuring a light exterior and expansive ocean views. A covered entryway welcomes guests, surrounded by tropical greenery. The picturesque setting highlights the home's elevation and proximity to the water.

Home in Captain Cook

5 out of 5 average rating, 31 reviews

4BR Paradise Oasis w/ Stunning Ocean Views

ThereseRating, 5 stars2 months ago

It is so delightful when ones expectations which are already high are completely surpassed. We enjoyed our stay so much at Christine‘s place. We were a big family and we loved the many different decks to relax and enjoy the beautiful view as well as the large kitchen and living room to gather and eat, laugh, play games and chat. Everything we could possibly need was provided. We really appreciated the cooler, boogie boards, and snorkeling gear, too. And oh that hammock !! If we come back to Kona, I would absolutely love to stay at Christine’s place again. Highly recommend! PS The driveway is super steep but it was all a part of the adventure! PPS We saw whales from the deck.

The exterior features a multi-level wooden home surrounded by tropical landscaping, including various plants and trees. A spacious driveway leads to the property, with a covered lanai visible on the upper level, inviting relaxation and enjoyment of the surrounding nature.

Home in Captain Cook

4.93 out of 5 average rating, 15 reviews

Romantic Tropical Retreat, 150 yds from the Ocean!

RebeccaRating, 5 stars1 month ago

Lovely and peaceful home in quiet neighborhood. Loved walking to Pebble Beach - snorkeling was fantastic. Definitely need shows on the beach as stones will scorch your feet. The house had great amenities and set up for cooking. Nearest grocery is 30 min away, so worth it to plan ahead and stock for several days. Fantastic vintage furniture -‘d great Hawaiian art throughout. Would definitely stay again and highly recommend.

A spacious living area features high wooden ceilings and large windows, allowing ample natural light. Two bright orange armchairs are complemented by a dark green chair. A dining table is situated nearby, with a view of the outdoor space visible through the glass doors.

Home in Waimea

Gorgeous, sunny Waimea 5-br. house with pool.

AaronRating, 5 stars17 months ago

my family and I had planned a Christmas getaway for months. We originally had a place booked, which turned out to be a sophisticated fraud. While scrambling through any and all options at the Honolulu airport, I stumbled on this place. It is no exaggeration to say that Stefan singlehandedly saved our vacation. The check-in was simple, the hosts were unbelievably responsive and communicated with us throughout our stay, the location was private and gorgeous, and the amenities were top notch. You can tell that a very recent renovation had just been completed as the house itself was immaculate. The house also had room for all 8 of us with the pool, rec room, backyard, 4 bedrooms, large kitchen, beautiful dining room, and ample square footage. Another high note was the close proximity to Waikaloa Village and Waimea and Hapuna State Beach. This place was absolutely worth switching islands for, and I would happily recommend it to anyone looking for a large venue or a bit of privacy.

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