Vacation rentals with a kayak in Kailua-Kona

Guest suite in Kailua-Kona

A spacious studio apartment features a King-sized bed with blue floral bedding. Natural light filters through two large windows, and a small table with a lamp stands beside the bed. A mini fridge and microwave are positioned nearby, while a potted plant adds a touch of greenery.

4.85 out of 5 average rating, 425 reviews

Gardenia Studio; Private, Close to Airport

The Gardenia Suite is a freshly remodeled, clean, hotel-style studio attached to a home—close to the Kona airport. Set up like a hotel room, it features a king-size bed, bright modern bathroom, TV, workspace/desk, and a tea & coffee station with mini fridge and microwave. Please note: This unit does not include a full kitchen. The unit is set back from the main road, but some light road noise may still be heard. A white noise machine is provided for your comfort if you are sensitive to sound.

LocationOutdoor spacesSleep quality

Condo in Waikoloa Village

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.

4.91 out of 5 average rating, 94 reviews

NEW! Expansive OceanView Retreat/Best Beaches/ AC

Hale Kai II loft..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 w new AC..very spacious penthouse w gourmet kitchen.

Outdoor spacesValueView

5.0 out of 5 average rating, 37 reviews

Townhouse in Puako

Private 2 Story Beach/Golf 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.

LocationOutdoor spacesGrill

5.0 out of 5 average rating, 8 reviews

Condo in Holualoa

Kona Paradise: 2BR w/ pools /near town & beachs

Bring your spirit of adventure to this newly remodeled second floor and centrally located Condo. Switch over to “Island Time." Outdoor toys (boogie board, beach chairs, cooler, beach umbrella, beach sand toys, ...) provided. With a 70-inch HD TV and two soft recliners, stream all your favorite shows or watch local channels. Plenty of cool air with two AC units. It is centered between two pool and hot tub areas with BBQs. Assigned free parking by the unit. Walking distance to town, 1.5 miles.

Outdoor spacesLocationLong stay

4.9 out of 5 average rating, 20 reviews

An aerial view showcases a tropical neighborhood surrounded by lush palm trees, with the shimmering blue ocean visible in the distance. The home features a sloped roof with solar panels and is located near a curved street that leads to the waterfront.

Home in Keauhou

Kona/Keauhou - ocean lifestyle

Enjoy an easy walk to access two bays and the wonderful clean, warm, blue waters of Kona. If an ocean life is your jam, you'll love our quiet He'eia Bay hale. Nestled amongst the Kona Country Club Golf Course, our oasis is a 9 iron from a small cove or 400 yrds to the more sheltered Keauhou Bay. Enjoy all that the ocean has to offer, we even have “toys” to get you out on or in the water. Complete with zoned air conditioning for those who need a bit of cooling from the abundant Kona sun.

Outdoor spacesLocationBeach

4.97 out of 5 average rating, 144 reviews

Lush greenery surrounds a well-maintained lawn that leads to a vibrant blue ocean. Palm trees and tropical plants enhance the natural setting, with gentle waves seen in the distance. The scene captures the essence of a serene waterfront environment.

Guesthouse in Keauhou

Kona Ocean Front Cottage on Keauhou Bay

Waterfront cottage on private, gated 1 acre estate. Close as you can get to an over the water bungalow in Hawaii. Direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walk to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor market. Two room suite. Queen bed. Living room with 50 in TV. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower. Couples and solo travellers only. No smoking.

ValueLocationCheck-in

Apartment in Waikoloa Village

4.97 out of 5 average rating, 31 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.

LocationOutdoor spacesPool

Superhost

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

4.93 out of 5 average rating, 149 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!

Outdoor spacesLocationBathroom

4.95 out of 5 average rating, 103 reviews

The lanai is furnished with a seating area featuring a wooden table and comfortable chairs. A ceiling fan provides airflow, while palm trees frame the sunset view over the horizon. Soft lighting and a calming ambiance are present, creating an inviting outdoor space.

Condo in Puako

Hale Honu -Turtle House Oceanview Luxury Penthouse

Welcome to Hale Hunu – Penthouse Paradise at Vista Waikoloa! This renovated 3rd-floor suite offers ocean, pool, and mountain views from a tiled wraparound lanai. Just a 7-min walk to A-Bay, shops, dining, and more. Enjoy 2BR/2BA, a full kitchen, washer/dryer, Smart TVs, Wi-Fi, and beach gear. Nestled on lush grounds near Hilton Waikoloa, with scenic walking paths. Peaceful, stylish, and perfect for up to 4 guests. Book now and enjoy your Big Island escape!

LocationValueIndoor spaces

A serene beachfront scene captures the sun setting over the horizon, casting warm hues across the sky and water. Weathered driftwood stretches toward the ocean, while gentle waves lap against a shore adorned with smooth stones, creating a tranquil atmosphere.

4.91 out of 5 average rating, 107 reviews

Puako Tropical Garden Retreat - Across from Beach

This serene Puako beach home offers 3 bedrooms and 2.5 baths—perfect for families, couples, or friends. Located across from a quiet beach access, enjoy uncrowded sunset strolls and turtle sightings. Minutes from top white sand beaches, luxury resorts, and golf. Now featuring brand new split AC units throughout for full-home cooling comfort. Relax in the tropical yard, dine outdoors, and enjoy all the beauty the Big Island has to offer.

ValueLocationIndoor spaces

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

4.82 out of 5 average rating, 39 reviews

Ocean & Golf Views | Remodeled Kona Villa w/ AC

🌺 Living on Island Time – Ocean & Golf View Retreat Experience the beauty of Kona from this oceanview retreat overlooking the golf course. This upgraded 2BR/2BA condo offers AC, full kitchen, pools, tennis, BBQs, and a private lanai for unforgettable sunsets. Walk to Keauhou Bay and nearby shops, or explore Downtown Kona and Two Step Beach just minutes away. A peaceful, upscale escape to relax and recharge.

LocationConditionBackyard

4.84 out of 5 average rating, 174 reviews

A spacious wrap-around lanai offers a panoramic view of the ocean and lush greenery. Palm trees frame the scene, while a small seating area invites relaxation. The deck features wood flooring and a metal railing, blending harmoniously with the surrounding tropical landscape.

Home in Captain Cook

KEALAKEKUA HOME STUNNING VIEW SPACIOUS ELEGANCE

This is a uniquely designed custom house with a 17-foot-high open beam ceiling. A wrap-around lanai (deck) opens towards a view of the expanses of the ocean, coast, and slopes of South Kona at the front of the house, and the mountain jungle to the back. We are in the middle of a tropical rainforest.

ValueOutdoor spacesGrill

Popular amenities for Kailua-Kona kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.93 out of 5 average rating, 117 reviews

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

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

LocationValueAccuracy

4.99 out of 5 average rating, 67 reviews

8 Seat Minivan | Hilton Pass | BBQ | Sleeps 8 | M4

ValueLocationCheck-in

Home in Waimea

4.5 out of 5 average rating, 6 reviews

Hina’s Fale (Waimea)

ValueLocationCondition

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

5.0 out of 5 average rating, 5 reviews

Gorgeous Waimea 5-br. house with pool, hot tub.

LocationIndoor spacesAccuracy

Come Stay Puako ~ Hosted With Aloha

Outdoor spacesLocationKitchen

A spacious studio room features a king-size bed, comfortable seating area with a modern chair, and a large flat-screen TV mounted on the wall. A balcony offers a partial view of the ocean. Natural light fills the room through floor-to-ceiling sliding glass doors.

Ocean Tower Resort Suite Partial Ocean View

Private room in Kailua-Kona

The room features a queen-sized bed with a light blue patterned coverlet and neatly arranged towels. A sliding mirrored closet door reflects the space, while a ceiling fan offers cooling comfort. A doorway leads to a bathroom, and natural light enters through the nearby window.

4.83 out of 5 average rating, 245 reviews

Rm 1: Hibiscus Room

Outdoor spacesLocationDecor

4.98 out of 5 average rating, 119 reviews

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

The Mango Cottage on Keauhou Bay

Outdoor spacesValueComfort

Other vacation rentals with a kayak

4.83 out of 5 average rating, 60 reviews

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

Kona Dream:2 Baths•Ocean V•Step to Downtown & Pier

ValueLocationNearby

4.83 out of 5 average rating, 6 reviews

A peaceful resort scene is depicted with a calm lagoon surrounded by lush greenery and palm trees. Two resort buildings frame the view, showcasing balconies and vibrant tropical landscaping. The clear water reflects the blue sky with scattered clouds, enhancing the serene environment.

Apartment in Puako

Paradise on the Big Island

Outdoor spacesKitchenDecor

5.0 out of 5 average rating, 7 reviews

Condo in Puako

Hale Nanea | FREE Beach Club access | AC

Outdoor spacesLocationBeach

5.0 out of 5 average rating, 7 reviews

The living area features a modern sectional sofa complementing two armchairs, positioned around a round coffee table. Natural light floods the space through sliding doors that open to a golf course view, while decorative elements enhance the welcoming ambiance.

Condo in Puako

Luxury + Privacy • Sleeps 8 • Beach Club Access

Outdoor spacesLocationBiking

A serene view shows the tranquil waters of Kealakekua Bay at sunset, framed by swaying palm trees. The sky transitions in soft hues of pink and purple, while a gentle wave laps against the rocky shoreline, creating a peaceful atmosphere.

Vacation home in Captain Cook

4.77 out of 5 average rating, 22 reviews

Oceanfront - Dolphin Retreat

LocationValueView

Condo in Kailua-Kona

4.62 out of 5 average rating, 34 reviews

Oceanfront condo, breathtaking views!

LocationValueNearby

A private balcony offers a table with seating for four, surrounded by palm trees and unobstructed ocean views. The space is complemented by a small side table, enhancing the outdoor dining experience.

Condo in Kailua-Kona

4.66 out of 5 average rating, 89 reviews

Top-Floor Kailua Bay Resort Condo w/ Ocean Views!

ValueLocationQuiet