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Guesthouse vacation rentals in Kailua-Kona

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Top-rated guesthouse rentals in Kailua-Kona

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Kailua-Kona
Tiny House in Kona - 5 Minute Walk to the Beach!
Mahalo nui for your Interest! After a year-long break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1000+ 5-Star Reviews and book with Confidence! This is a real Tiny House on Wheels with an additional connected open air and fully screened kitchen for dining and relaxing. You'll love this "rustic" and private experience in an upscale neighborhood just 4 miles south of downtown Kona! And, you are only a 5 Minute Walk to Magic Sands - the best beach in town!
$139 per night
Guest favorite
Guesthouse in Kailua-Kona
Spectacular Views of Kailua-Kona
Aloha and e komo mai to our Ohia Guest House in beautiful Kailua-Kona. Ohia Guest House is your well equipped home away from home, it has everything you will need for a comfortable holiday on The Big Island. We live at a cooler elevation of 1000 feet with pleasant tropical breezes. Our property is on 1.5 acres of tropical landscaping. Ocean views abound, perfect for sunset watching and seeing real-time surf conditions. In the evenings enjoy stargazing and the sounds of the tropics.
$150 per night
Guest favorite
Guesthouse in Kailua-Kona
Cool & Cozy - AC & Wi-Fi - 4 Blocks from Ocean
Our enchanting private guest house is just 4 blocks from the ocean. Sparkling clean & cool. 5 minute drive to beautiful Magic Sands Beach or Kona Town featuring food, shopping & entertainment. Newly built. Air Conditioning & fast fiber optic WiFi. Cool down after a warm day at the beach. Need a rental car? Ask us about our cars available through Turo. A private haven after exploring the many wonders of Hawai’i Island. We are very proud of our reviews & how happy our guests are.
$145 per night

Popular amenities for Kailua-Kona guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Holualoa
Holualoa Studio Cottage - Incredible Ocean Views!!
$154 per night
Guest favorite
Guesthouse in Kailua-Kona
Treehouse Ohana
$183 per night
Guest favorite
Guesthouse in Kailua-Kona
Modern Apartment with Ocean and Mountain Views
$139 per night
Guest favorite
Guesthouse in Kailua-Kona
180 degree ocean view, private pool
$200 per night
Guest favorite
Guesthouse in Captain Cook
Garden Cottage Ohana
$182 per night
Guest favorite
Guesthouse in Kamuela
Kohala Loke Lani, Big Island
$235 per night
Guest favorite
Guesthouse in Waikoloa Village
Synergy Near Golf & Beach
$124 per night
Superhost
Guesthouse in Captain Cook
Kealakekua Bay Bali Cottage -steps from Bay
$190 per night
Guest favorite
Guesthouse in Holualoa
Holualoa Ekahi -Country guest house,Taxes included
$166 per night
Superhost
Guesthouse in Kailua-Kona
Exotic fruit farm Ohana with lava tube cave!
$225 per night
Guest favorite
Guesthouse in Waimea
Sunset House by the Sea
$136 per night
Guest favorite
Guesthouse in Waimea
Mango Hale Cottage
$250 per night

Guest house rentals with a patio

Guest favorite
Guesthouse in Holualoa
The Light House~King
$198 per night
Guest favorite
Guesthouse in Kailua-Kona
Romantic Cabin Treehouse in Hawaii Cloud Forest
$358 per night
Guest favorite
Guesthouse in Honokaa
Romantic waterfall cabin in the rain forest
$266 per night
Guest favorite
Guesthouse in Kailua-Kona
Modern, Peaceful & Private 1-BR Oasis/Ohana
$139 per night
Guest favorite
Guesthouse in Kailua-Kona
Sea View Studio Getaway
$165 per night
Guest favorite
Guesthouse in Kailua-Kona
Breath Taking Views Ohana
$150 per night
Guest favorite
Guesthouse in Kailua-Kona
Cozy Vintage Inspired Hawaiian Guest Cottage
$148 per night
Guest favorite
Guesthouse in Kailua-Kona
Fresh & Bright Tropical Getaway
$156 per night
Guest favorite
Guesthouse in Kailua-Kona
Tropical+Peaceful Guava Cottage
$314 per night
Guest favorite
Guesthouse in Keauhou
Kona Ocean Front Cottage
$450 per night
Guest favorite
Guesthouse in Holualoa
Kanaho Place: Holualoa Guesthouse
$159 per night
Guest favorite
Guesthouse in Holualoa
"Beachside Cottage" close to beaches & Kona
$145 per night

Guest house rentals with a washer and dryer

Superhost
Guesthouse in Kailua-Kona
Small Private Studio Close to Airport
$85 per night
Guest favorite
Guesthouse in Kailua-Kona
Hawaiian Mt. Retreat Suite A
$135 per night
Guest favorite
Guesthouse in Holualoa
Holualoa Jungle Getaway (15 min from Kona)
$119 per night
Guest favorite
Guesthouse in Kailua-Kona
Elegant & Peaceful Studio
$138 per night
Guest favorite
Guesthouse in Kailua-Kona
Kimo’s Getaway
$195 per night
Guest favorite
Guesthouse in Holualoa
Holualoa Country Home
$150 per night
Guest favorite
Guesthouse in Kailua-Kona
AC | 1 Gig | BBQ | Kitchen | Workspace | Hammock
$150 per night
Guest favorite
Guesthouse in Kailua-Kona
Hulilau
$110 per night
Guest favorite
Guesthouse in Kailua-Kona
Big Lanai w/ outdoor living! Ocean view & breezes!
$310 per night
Superhost
Guesthouse in Captain Cook
Kona Paradise Ohana Studio
$150 per night
Guest favorite
Guesthouse in Kailua-Kona
The Banyan House, with e-bike & car rental options
$248 per night
Guest favorite
Guesthouse in Kailua-Kona
Hale Ku'uipo in Kailua Kona HI
$149 per night

Quick stats about guesthouse rentals in Kailua-Kona

Total rentals

40 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

40 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

5.2K reviews

Nightly prices starting at

$80 before taxes and fees

Destinations to explore

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