Family-friendly holiday rentals in Kailua-Kona

Private Pool - 180° Ocean View - Minutes to Beach

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

Wailima Beach House, Kona, Magic Sands Beach

Wailima Beach House is real island living while vacationing here on the Big Island. The home features beautiful Asian antiques, bamboo and rattan furniture plus Pacific themed artworks. The garden setting provides the perfect escape from life's hustles and bustles. Walking distance to Magic Sands Beach Park and easy drive to Kahalu'u snorkel beach means you really don't have to go anywhere else. Keahou Shopping Center is 10 min. away with KTA grocery store plus boutique shops and restaurants.

Exceptional Oceanview Home - Pool & Stunning View

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

Kona Coffee Estate Retreat | Ocean & Sunset Views

Escape to our family-friendly 3.5-acre Kona Coffee Farm, nestled in the mountains minutes from beaches, 15 min to Kailua-Kona, and 5 min to Captain Cook. Kids can feed our friendly chickens, spot geckos, and explore the lush grounds filled with coffee trees, fruit, and flowers. The 3BR, 2BA modern farmhouse includes a spacious lanai, perfect for family meals, morning coffee, and stargazing. Enjoy cool mountain breezes, a refreshing escape from the coastal heat, and the magic of Kona Coffee.

Amazing Kona Sunset View - Sleeps 4

Two Bedroom + One bath with an amazing sunset view! Sleeps 4! Take advantage of our September 5-day discounts. We’re off on Holiday family members will be managing the apartment. Kona has the best beaches, best food, and nicest people!! We’re close to Saddle Road to Hilo and both upper and lower roads circling the Big Island. Book NOW. Read our reviews. Check out the photos. You will love how quiet the place is and private. We will also work with you on pricing for longer term rentals.

Beautiful, Spacious Home w/Expansive Ocean Views

This is a HOSTED RENTAL and we are fully HB 108 COMPLIANT, but you won't see us unless you need us-on site or by text 7 days a week. This is not a party house. We rent to fun-loving folks who seek tranquility in paradise. Bookings made after 6/28/21 include all taxes and fees. Guests walk in and we see wow on their faces: gourmet kitchen, huge bedrooms.. "perfect for a family reunion" "cool at night, was just right" "close to the best beach in Hawaii" "amazing sunset views"

Halia Hale

Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

Mini Plantation with a View

2300 sq.ft home on over an acre is perfect for time with family & friends. 10 minutes from downtown Kona, in Holualoa, with organic coffee, fruit trees, and flowers. There is a roof-top games with ping-pong room overlooking the garden. Paddle boards, snorkeling gear, basketball, and lots of games are also provided. Entertaining is easy on the huge lanai with bbq and a kitchen equipped with cooking staples and equipment. Home is on-property hosted.

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Beautiful view home 4 bedrooms, Heated Pool! Big private yard, gourmet kitchen, 2 car garage, BBQ. Each bedroom leads out to the lanai(s) through French doors. Comfortably sleeps 8 in beds but can accommodate up to 10 maximum. Less than 10 minutes to awesome beaches, shopping, and restaurants. We now offer air-conditioning for a nominal fee. Please let us know if you would like to add this option to your reservation, the cost is $20/night.

Family-Friendly 4BR Oasis by Magic Sands

Escape to this spacious island retreat featuring an open-concept living area, gourmet kitchen, and beautifully designed coastal interiors. Relax on the covered lanai with outdoor dining, lounge seating, BBQ, and a lush tropical backyard. The home offers luxurious king suites, a spa-inspired primary bath with a Jacuzzi tub, and is just minutes from Kona's best beaches, snorkeling, shopping, and dining. 🌺

Tax all included! Luxury Kolea at Waikoloa Resort

Luxury ocean front property Kolea A'Bay ! Gated community and 24/7 security with high maintenance for everything in Kolea. peaceful and centrally-located place with private pool club house right by the ocean and private road to the ocean. You can walk to the LavaLava sunset lounge on A bay and walk to the King shopping center where upscale stores are located with restaurant and grocery store.

Enchanting Eco-Hideaway: Bohemian Retreat

~ Open-Air Living on a lush mango farm ~ 1 mile from best snorkeling in Kealakekua Bay ~ King bed, hammock, fully-equipped kitchen, BBQ ~ Unique Balinese Bohemian Treehouse style ~ Indoor-Outdoor, Open-Air, Nature-Based Experience ~ 180° views from the Master Bedroom (screened in) ~ Private outdoor shower surrounded by Plumerias