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, 428 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.

LocationValueBeach

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.

4.92 out of 5 average rating, 95 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 spacesLocationAccess

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 spacesView

4.98 out of 5 average rating, 120 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

Cottage on private, gated, 1 acre waterfront estate. Swim, surf, kayak, and snorkel from yard. Watch dolphins and boats in the bay. Walk to manta ray, snorkeling, kayaking, whale and dolphin tours, golf, restaurants, movie theater, and outdoor market. Two room suite. King bed. Full kitchen. 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. 100% non-smoking property inside and out.

ValueLocationHospitality

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 spacesLocationView

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

Kona Alii Condos ocean view property with your own covered parking stall! On 2nd floor with secure elevator access! Great for bring luggage, food/water etc. No more lugging stuff up the stairs! Great partial ocean views right off your lanai! Steps to ocean, historical landmarks, beaches, shops, restaurants, night life & pier. Features rare 1-bed/2-bath layout, in-unit washer/dryer & full kitchen. Perfect for up to 4, with fold out cot if needed. Relax & enjoy your ultimate value getaway!

ValueOutdoor spacesLong stay

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.

Outdoor spacesLocationKitchen

4.93 out of 5 average rating, 149 reviews

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

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 spacesValueGetting around

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.

4.95 out of 5 average rating, 103 reviews

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!

ValueLocationGetting around

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.

Outdoor spacesValueHiking

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.

LocationGetting aroundParking

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.

LocationValueWalkability

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!

ValueLocationHiking

4.99 out of 5 average rating, 67 reviews

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

Outdoor spacesValueSleep quality

Home in Waimea

4.5 out of 5 average rating, 6 reviews

Hina’s Fale (Waimea)

ValueLocationBeach

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.

LocationCheck-inKitchen

Come Stay Puako ~ Hosted With Aloha

Outdoor spacesLocationHospitality

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

ValueOutdoor spacesGrill

Superhost

New place to stay

Mele Mele 3BR Puako Retreat Steps to Ocean

Other vacation rentals with a kayak

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 spacesHospitalityComfort

5.0 out of 5 average rating, 7 reviews

Hale Nanea | FREE Beach Club access | AC

LocationOutdoor spacesBeach

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.

5.0 out of 5 average rating, 7 reviews

Luxury + Privacy • Sleeps 8 • Beach Club Access

LocationOutdoor spacesIndoor spaces

Superhost

Apartment in Holualoa

New place to stay

Amazing New Fully-Renovated Oceanfront 2 Bdr Condo

Condo in Kailua-Kona

4.62 out of 5 average rating, 34 reviews

Oceanfront condo, breathtaking views!

ValueLocationAccess

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

4.78 out of 5 average rating, 23 reviews

Oceanfront - Dolphin Retreat

Outdoor spacesLocationTV