Holiday rentals with a kayak in South Kona

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.

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.

NEW Sweeping Ocean View Retreat/Golf/Pool/PB Court

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... a very spacious penthouse w gourmet kitchen.

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.

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!

Three-bedroom Hawaiiana. Visit Volcanoes & more!

Looking for everlasting memories of your big island trip? Hawaiian Plantation Style home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate. Explore the island by kayaking in Hilo Bay. Complimentary rental of two ocean kayaks for the guests listed in the booking. Taxes are included in rental rate 17.75% total. GE & TA-155-977-6256-01

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.

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!

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.

Downtown Hilo Studio

A hidden gem in Hilo, this studio is attached to our family home, situated in a safe, slightly hilly walk from downtown Hilo. This studio unit has its own private entrance through the side gate of the main house. The unit and its lanai look out onto our backyard where our pet goats reside. They are timid yet friendly, especially if your come bearing ti leaf and goat treats. Drop us a line if youʻre interested in staying!

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.

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.