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.

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.

Hawaii’s holualoa hideaway

Escape to this stunning 6-bedroom estate on 5 lush acres in Holualoa—just 15 minutes from beaches, shops, and restaurants. Thoughtfully designed with bamboo floors, high-beamed ceilings, and antique touches, the home offers charm and luxury. Relax in two private pools, soak in the hot tub, and enjoy ocean-view sunsets. Surrounded by tropical gardens and visited by wild peacocks, parakeets, and friendly sheep, this is your perfect Big Island retreat.

Kealakekua Bay Haven - Loke Lanai, Steps from Bay

Kealekekua Bay Haven has breathtaking views of Kealakekua Bay and surrounding area. Beautiful sunsets every night, steps away from the pier and beach. There is Kayaking available, dolphin watching, swimming and snorkeling. Come rejuvenate and renew - in our amazing house with the million dollar view from the rooftop balcony 360 views of sunsets and Captain Cook Monument. Great place for guests that enjoy nature.

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.

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.

Kona 1BR Condo w/ Pool, Office, Walk to Beach

Wake up in the heart of sunny Kailua-Kona, sip fresh-ground Kona coffee on your private lanai, then stroll five minutes to the waterfront, cafés, and the open-air farmers’ market. Whether you’re dialing into work on dual monitors or floating in the palm-lined pool, this newly upgraded 1-bedroom condo is built for travelers who refuse to choose between productivity and play.