Holiday rentals with a kayak in Kailua-Kona

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Top-rated rentals with kayak in Kailua-Kona

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Guest favourite

Home in Captain Cook

5 out of 5 average rating, 36 reviews

4BR Paradise Oasis w/ Stunning Ocean Views

Enjoy panoramic ocean views from every room in our spacious tri-level home near secluded Pebble Beach. Located south of Kona in Kona Paradise, this 4-bedroom retreat features an open floor plan with kitchen, dining, and living areas on the main level. Three large lanais offer stunning sunset views. Upstairs, the primary suites provide privacy and relaxation with an expansive lanai, cozy seating, and a hammock perfect for napping to the sound of waves or watching sunsets in the island breeze.

Guest favourite

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 favourite

Apartment 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 favourite

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 favourite

Guest suite in Kailua-Kona

4.89 out of 5 average rating, 336 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 favourite

Flat 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 favourite

Home in Kailua-Kona

4.92 out of 5 average rating, 133 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 favourite

Guest house 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

Flat 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.

Guest favourite

Guest suite in Kailua-Kona

4.92 out of 5 average rating, 429 reviews

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.

Top guest favourite

Guest house 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.

Guest favourite

Apartment in Puako

5 out of 5 average rating, 10 reviews

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