Vacation rentals with a kayak in Kailua-Kona

5 out of 5 average rating, 15 reviews

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

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.

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, 59 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.

4.98 out of 5 average rating, 94 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 with direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. Queen bed. Living room with 50 in TV. Bathroom with large shower. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower.

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.

4.89 out of 5 average rating, 353 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.

Apartment in Waikoloa Village

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.

5 out of 5 average rating, 16 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.

5 out of 5 average rating, 4 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 Waimea

Luxury + Privacy • Sleeps 8 • Beach Club Access

Kulalani in the Mauna Lani Resort • 68-1118 North Kaniku Drive #503 • NEW to the Rental Market! Kulalani 503 is a luxurious townhome located in the highly desirable Mauna Lani Resort. Boasting a lavish master suite featuring a spacious tile shower and indulgent soaking tub. With a generous Golf Course-facing lanai, it offers stunning views and ample space for relaxation. Ideal for families or groups, this retreat accommodates up to 8 guests, promising a memorable vacation experience.

4.92 out of 5 average rating, 135 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!

Guesthouse in Kailua-Kona

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.

5 out of 5 average rating, 15 reviews

Kona Ohana Retreat – Pool, Cabana & Island Living

Escape to your private Hawaiian oasis in Kona! Relax by the sparkling pool, unwind under the cabana with a tropical drink, and enjoy the true spirit of island living—just minutes from beaches, snorkeling, coffee farms, and Waipiʻo Valley adventures. Welcome to our Kona ohana retreat, a bright and spacious getaway designed for comfort, relaxation, and a touch of aloha. Perfect for couples, families, or remote workers looking to balance island adventure with modern comforts.

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.

4.92 out of 5 average rating, 439 reviews

Da Pool Hale - 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.

4.86 out of 5 average rating, 49 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-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.

4.85 out of 5 average rating, 20 reviews

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

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.

5 out of 5 average rating, 11 reviews

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

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

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, 108 reviews

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

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

4.89 out of 5 average rating, 18 reviews

Romantic Tropical Retreat, 150 yds from the Ocean!

Home in Waimea

New place to stay

Villa at Mauna Kea Resort - Ocean & Golf Views

5 out of 5 average rating, 17 reviews

A spacious living area is furnished with a dark blue sectional sofa and a matching ottoman. Natural light floods in through expansive windows, showcasing lush outdoor landscaping. A ceiling fan circulates air, while a television is mounted on a white media console, with decorative shelving on either side.

Home in Kealakekua

Mountain Oasis: Modern Plantation Home

4.99 out of 5 average rating, 84 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

5 out of 5 average rating, 37 reviews

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

4BR Paradise Oasis w/ Stunning Ocean Views

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.

Home in Waikoloa Village

Ocean Tower Resort Suite Partial Ocean View

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

Other vacation rentals with a kayak

Condo in Waimea

FREE Golf Package | AC | Lagoon Style Pool

4.83 out of 5 average rating, 24 reviews

A vibrant sunset is captured over the ocean, with rich orange and red hues filling the sky. Silhouetted palms and trees frame the scene, enhancing the serene coastal view. The horizon features the sun setting into the water, creating a peaceful natural ambiance.

Guest suite in Kailua

Kona Sunset Ocean View Two Studio Oasis

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.

4.88 out of 5 average rating, 456 reviews

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

Condo in Hawaii County

New place to stay

Oceanview Renovated 3BR Condo Across from Beach

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, 317 reviews

Gardenia Studio; Private, Close to Airport

Condo in Waikoloa Village

A landscaped pool area is visible, surrounded by lush tropical vegetation and palm trees. The inviting blue water of the pool is complemented by several lounge chairs and umbrellas, providing shaded resting spots. A clear blue sky and sunlit surroundings enhance the tranquil atmosphere.

5 out of 5 average rating, 5 reviews

Family Fave! Close to A-Bay, steps to heated pool!

4.96 out of 5 average rating, 28 reviews

An outdoor patio area features a circular metal dining table surrounded by six chairs. Lush greenery and palm trees frame the view, while a volcanic rock landscape adds visual interest in the background under a clear blue sky.

Condo in Puako

Luxury Golf Villa G3 - 3 Bedrooms Golf and Beaches