Smoking-friendly holiday rentals in Kailua-Kona

Pure Aloha Ocean-view Jr Suite w/ Lanai

Wake up to Pacific breezes and pour your morning Kona coffee on a lanai overlooking lush trees and a view of the ocean, then head to the shore for snorkeling, beach sunsets, or whale watching. This jr suite delivers island comfort and easy-going convenience: fresh tangelos , reliable WiFi, outdoor seating, and all the beach gear you need. If your here to explore the Big Island, or unwind under tropical sunsets, this is your home away from home.✅ Kona coffee provided ✅ Snorkel gear & beach towels

Hawaiian Home w/Stunning Sunsets

Experience breathtaking Hawaiian sunsets at our serene, brand-new house! Sleeps 14 with 3.5 baths, a spacious main house & private guest house. Enjoy open living spaces, lush outdoor areas, cooler temperatures at higher elevation, a gourmet kitchen, WiFi, BBQ, tennis, basketball & pickleball courts, and plenty of room to gather or relax. Perfect for families, group getaways—quiet, private, and designed for unforgettable memories under the Hawaiian sky. Only 15 minutes from downtown and airport.

The Dome at Ulu Inn: Luxury Couples Retreat, Kona

Overlooking the beautiful Kona Coast...The Dome at Ulu Inn says: "Aloha...let's Disconnect, to Reconnect" Nestled within a gated 5 acre estate, Settle into our exclusive Geodesic Dome suite...experience elevated glamping, designed for ultimate relaxation and ensured seclusion from the outside world. THE DOME & neighboring unit THE CUBE, are an ample distance apart, providing privacy from each other. You may get up close and personal with our Goats, Pigs, Geckos & wild birds that roam freely.

Lehua Lounge in the Heart of Downtown Kona

This place truly is hard to beat! Just 10 minutes walk to all Kona town, the beach & pier. In a peaceful neighborhood where you don’t hear any traffic noise at all. Newly installed AC keeping you cool & comfortable throughout the entire home. AC in both bedrooms as well as ceilin fans and floor fans. 2 bedroom, 2 bath townhouse with private lanai gives a feeling your in a secluded area & also as close as you can be walking anywhere to all Kona town offers. This is the vacation house for you!

Bridge unit 2/2 AC No stairs

Country Club Villas is a luxury condominium located on the 17 Fairway, Kona Country Club golf course w/3 swimming pools with BBQ’s & hot tubs, and 2 tennis courts all on site. BRIDGE UNIT NO STAIRS!! HUGE Lanai w/BBQ AMAZING OCEAN/GOLF VIEWS Within walking distance to Keauhou Bay & Shopping Center Master Queen bed w/in-suite vanity and separate walk-n-shower Spare bedrm w/Queen bed This spacious 2 bedrm 2 bath has Fans in all rooms including kitchen making cross breeze of Mountain and Ocean.

Paniolo Country Ohana - Big Skies, Starry Nights

Rolling hills, green pastures, cow country - Cool, quiet and private. We are centrally located in Waimea on the Big Island with a 5 minute drive to town, shopping, and the BEST farmers markets on island. It is also a 20 - 30 minute drive to the BEST beaches on island. Enjoy views of snowy Mauna Kea (wintertime) with it's famous observatory. Often warm, sunny days and incredible starry nights! Dogs are welcome! (2 Limit). Unfortunately, we do not accept other types of pets.

Pua Blossoms' Escape

My house is located about 5 miles south of Kailua town. It's two blocks away from White Sands Beach & a mile from Kahalu'u Beach. The kitchen, living room, dining room , are in the center of house and each bedroom suites are on opposite sides of shared spaces. I have solar , AC , surfboards, and other water toys ... I have three pets two dogs and 2 year old female Indian ringneck bird . She is very loud in the morning. I suggest you bring the noise canceling headphones…

Mauna Loa Suites

Beautiful and elegant spacious suites in Kamuela, Hawaii. Spectacular panoramic ocean views along with majestic sceneries of the 2 greatest mountains on earth. Mauna Kea and Mauna Loa. Mauna Kea is the tallest mountain on earth measuring over 10,000 meters (33,000 feet) and Mauna Loa is calculated to be over 75,000 Kilometers to the 3rd. (18,000 cubic miles) which is the biggest mountain on earth. This exclusive - private rooms is a treasure for you to experience.

Rose Garden Suite

Discover the magic of Belle Vue Kona B&B, a hidden gem perched in a one-of-a-kind location overlooking the historic Kealakekua Bay. Here, you’ll enjoy breathtaking views of the Pacific Ocean and the panoramic beauty of the South Kona coastline. Set on a lush four-acre Kona coffee farm, our property is also home to avocado, papaya, and banana trees—offering an authentic taste of island living.

Cool Coffee Shack Farm Stay - Comfort in Nature

In the Kona Coffee Belt, this is an 8-acre working coffee farm with several dwellings, including a rustic wooden coffee shack which is the primary space for guests. The space is light and airy, with art from around the world, musical instruments and friendly animals outdoors. We are tucked up a windy road above Kealakekua Bay and the Captain Cook Monument, near the best snorkeling/kayaking.

Holualoa Gardens 203

Welcome to your tropical getaway in Kailua-Kona! This spacious 1-bedroom, 1-bath condo is in a charming complex just off Aliʻi Drive, with a bright, colorful interior. Sleeps up to 4 with a king bed and queen sofa bed. Enjoy a fully equipped kitchen, AC, and a peaceful pool with sun deck. Walk across the street for ocean sunsets, beaches, and markets—an ideal home base on the Big Island.

Downtown 1BR Condo AC, Pool, BBQ & Walk to Beach

Escape to our upgraded 1-BR Kailua-Kona condo, perfect for work & play! This space comfortably fits 4, featuring a dedicated office with ultra fast Wi-Fi, a sparkling pool, and a full kitchen. Just a 5-min walk to the waterfront, cafes, and farmers' market. Enjoy modern comforts and a prime location for your Big Island adventure.