Holiday rentals with a kayak in Kailua-Kona

Apartment 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, 88 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 spacesLocationAir conditioning

5 out of 5 average rating, 7 reviews

Hale Nanea | FREE Beach Club access | AC

Elegant 2-bed, 2-bath Fairways at Mauna Lani condo offering resort living with FREE Private Beach Club access. Enjoy central A/C, lagoon-style pool & spa, fitness center, golf course views, and upscale island design. The open living space features a chef’s kitchen, stylish furnishings, and a private lanai with wet bar & grill—perfect for sunset dining or spending time with friends. Walk to beaches, snorkeling, dining, and world-class golf in one of the Big Island’s most prestigious communities.

Outdoor spacesLocationFamily

5 out of 5 average rating, 31 reviews

A lagoon-style pool is surrounded by lush tropical landscaping and palm trees. Natural rock formations are integrated into the pool design, creating a serene atmosphere. Nearby, charming two-story villas are visible, blending with the vibrant greenery under a clear blue sky.

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 spacesComfort

4.98 out of 5 average rating, 113 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.

LocationOutdoor spacesShared spaces

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 spacesLocationWalkability

4.96 out of 5 average rating, 28 reviews

Flat in Waikoloa Village

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 spacesLocationSleep quality

4.93 out of 5 average rating, 147 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 spacesLocationCleanliness

Guest suite in Kailua-Kona

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, 430 reviews

Jasmine Studio; King Bed, Close to Airport

Conveniently located just 5 minutes from the airport and 15 minutes to downtown Kailua-Kona, this inviting space offers comfort and ease. Enjoy vaulted ceilings, a cozy lanai for morning coffee, a spacious bathroom with double vanity, and a well-equipped kitchenette. Stay cool with powerful A/C or relax with the tropical breeze. Reliable WiFi and a large Roku TV make it easy to unwind. Automated check-in and flexible booking ensure a smooth, stress-free stay.

LocationValueAir conditioning

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, 99 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!

LocationValueTV

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, 104 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.

LocationOutdoor spacesGetting around

4.83 out of 5 average rating, 60 reviews

A view of the lush garden and ocean can be seen from a window. Tropical plants frame the scene, while a sun lounger is positioned by the pool. The distant waves and palm trees add to the serene ambiance, creating a relaxing vacation setting.

Apartment in Kailua-Kona

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

Kona Alii 2nd-floor condo right across the ocean with partial ocean views off the lanai! Steps to ocean, downtown & pier. Features rare 1-bed/2-bath layout, in-unit washer/dryer, and full elevator access. Perfect for up to 4 guests. Extremely walkable location right across from the ocean. Relax & enjoy the ultimate value getaway!

LocationOutdoor spacesHospitality

4.84 out of 5 average rating, 170 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.

LocationOutdoor spacesQuiet

Popular amenities for kayak rentals in Kailua-Kona

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

New place to stay

8 Seat Minivan | Hilton Pass | BBQ | Sleeps 8 | M1

4.93 out of 5 average rating, 115 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!

LocationOutdoor spacesKitchen

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

4.98 out of 5 average rating, 64 reviews

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

LocationValueBeach

Come Stay Puako ~ Hosted With Aloha

Outdoor spacesLocationCondition

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

ValueLocationLaundry

Home in Waimea

4.5 out of 5 average rating, 6 reviews

Hina's Fale (Waimea)

ValueLocationHospitality

Other holiday rentals with a kayak

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 out of 5 average rating, 6 reviews

Luxury + Privacy • Sleeps 8 • Beach Club Access

Outdoor spacesLocationSleep quality

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.

Apartment in Kailua-Kona

4.66 out of 5 average rating, 88 reviews

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

LocationValueSleep quality

4.86 out of 5 average rating, 22 reviews

A spacious sleeping area features a wooden bed with a decorative floral bedding set. A mini fridge stands beside the bed, with a television mounted on the wall. Natural light filters in through large windows adorned with curtains, highlighting the vaulted wooden ceiling.

Guest suite in Holualoa

Paradise Nest Studio Suite Ocean View

ValueLocationCleanliness

Aerial view of a secluded beach, featuring soft sand and vibrant turquoise waters. Lush greenery borders the beach, creating a natural oasis. The clear, calm water showcases hints of coral and marine life beneath the surface, inviting exploration and relaxation.

Place to stay in Captain-Cook

Oceanfront "Old Hawaii" Retreat

Guest house in Kailua-Kona

The exterior showcases a well-lit two-story home framed by lush tropical landscaping. A shimmering pool reflects the evening sky, while multiple patios and balconies extend from the building, inviting relaxation. Decorative plants enhance the charming atmosphere, providing an inviting outdoor space.

4.85 out of 5 average rating, 20 reviews

Aloha Kona Villa – Pool, Grill, Laundry, & Parking

Outdoor spacesLocationNearby

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.

Flat in Keauhou

4.83 out of 5 average rating, 35 reviews

Ocean & Golf Views | Remodeled Kona Villa w/ AC

LocationFamilyAccuracy

Apartment in Holualoa

Big Island Escape – Pools, Palms & Adventure