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 snorkeler glides gracefully through crystal-clear waters alongside a sea turtle, showcasing a serene underwater scene. Sunlight filters through the water, illuminating a rocky ocean floor that provides a natural habitat for marine life.

Townhouse in Waimea

5 out of 5 average rating, 11 reviews

Private 2 Story Beach Villa at Mauna Lani

Situated on the beautiful Kohala Coast in the heart of the luxurious, world renown Mauna Lani Resort, we welcome you to our 2 story Beach Villa. Poised alongside the 4th fairway, this luxuriously furnished three bedroom, three bath home provides an excellent view of the golf course and scenic mountains. This home is 2,321 sq feet and features many amenities including the use of a huge, lagoon style pool with hot tub, workout room, high speed internet. Includes access to the PRIVATE BEACH CLUB.

Guest favorite

A spacious lounge area is highlighted by a light-colored sectional couch, positioned to offer views through large windows. Natural light fills the space, with a textured area rug beneath a wooden coffee table. Greenery is present, enhancing the connection to the outside landscape.

Condo in Waikoloa Village

4.91 out of 5 average rating, 57 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, 82 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

4.89 out of 5 average rating, 329 reviews

Jasmine Studio; King Bed, Close to Airport

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, 27 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, 15 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

4.92 out of 5 average rating, 132 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!

Guest favorite

A well-lit kitchenette area features a refrigerator, microwave, and a hot plate, accompanied by open shelving displaying kitchenware. A dining table with four chairs sits adjacent, while large windows offer a view of the coastline and surrounding greenery.

Guesthouse in Captain Cook

4.98 out of 5 average rating, 122 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.

Superhost

A serene lanai offers two chairs and a small table, with expansive views of lush green grass and palm trees. The ocean is visible in the background, while a colorful sunset casts a soft glow across the landscape, enhancing the tranquil setting.

Apartment in Keauhou

4.83 out of 5 average rating, 18 reviews

New Remodeled | Ocean & Golf Views | AC | Lanai

Welcome to Living on Island Time with Ocean view and front row to the golf course on the lanai. We took great care to prepare our unit and I hope, you relax with the whole family! This spacious unit is the unit # 130 in Country Club Villa, located on the Kona Country Club Golf Course and offers two bedrooms, two bathrooms, and a fully equipped kitchen. Enjoy ocean views and a front row to the golf course on the lanai. Pool, Tennis, Pickleball, BBQ, and more.

Superhost

A refreshing pool is framed by lush tropical greenery and wooden decking. Sun loungers with umbrellas are positioned around the pool, creating a relaxing outdoor space. A shaded gazebo is visible in the background, offering additional seating and a tranquil retreat.

Guest suite in Kailua-Kona

4.88 out of 5 average rating, 446 reviews

Kona-Amazing sunset, Ocean/POOL/AC/Great loc

We look forward to welcoming you to our property in the beautiful neighborhood of Kona Palisades. Centrally located in the heart of the Gold Coast of Kona. Less than 8 min away from Kona Airport,15 min away from Kua Bay and Kona Alii Dr.! We are located at 1,150 feet above sea level, this elevation is perfect for escaping the heat of downtown and cooling off after a day at the beach. Awaken to singing birds as the sun slowly rises over the Kona coastline.

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 Villa | 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.

Superhost

The image captures a serene pool area surrounded by lush greenery and tropical palm trees. In the background, the ocean is visible alongside a sunset that casts warm hues over the scene. A few lounge chairs sit by the pool, inviting relaxation.

Condo in Kailua-Kona

4.85 out of 5 average rating, 47 reviews

Kona Dream-Ocean, Beach, Downtown, Elevator

Kona Dream 1 bedroom, 2 bathroom, brings you right downtown Kailua-Kona, amazing sunset/ocean views and resturants, shopping, beaches, night life, and so much more all in walking distance. New 14” cooling gel/memory form ultra comfort queen mattress. You have a private balcony to relax and enjoy the Pool and Ocean with amazing Sunsets. Full kitchen, Elevator, Free parking covered stall, new washer and dryer.