
Guesthouse holiday rentals in Kailua-Kona
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Top-rated Guesthouses in Kailua-Kona
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua-Kona guesthouses
Family-Friendly guesthouses

Kona Coffee Mountain Getaway

Sunset House by the Sea

Kealakekua, HI Wekuke Ranch ohana

Ocean View Guesthouse, Kona!

Kohala Loke Lani, Big Island

Oceanview Zen Luxury Coffee Estate Home

Walk 5 min. to see dolphins in Kealakekua Bay

The Sun, Moon & Stars at Konarado
Guesthouses with a patio

All About The View!

3-min walk to beach | King bed | Newly Renovated!

Ohana With Private Pool & Jacuzzi

Cozy Vintage Inspired Hawaiian Guest Cottage

Fresh & Bright Tropical Getaway- Ocean View

Bright Island Hideaway | King Bed + Ocean Views

KoKo Cottage: Adorable 2-Bedroom Ocean View/Lanai

Waimea Honu Cottage- Cozy & Relaxing
Guest house rentals with a washing machine and dryer

AC | 1 Gig | BBQ | Kitchen | Workspace | Hammock

Mango Hale Cottage

Kimo’s Getaway

Big Lanai w/ outdoor living! Ocean view & breezes!

Holualoa Ekahi -Country guest house,Taxes included

Holualoa Country Home

“Special Rate” Private, Waimea Ohana (Guest House)

Elegant & Peaceful Studio
Quick stats about guesthouse rentals in Kailua-Kona
Total rentals
40 properties
Nightly prices starting at
$122 AUD before taxes and fees
Total number of reviews
4.9K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Destinations to explore
- Beach house rentals Kailua-Kona
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- Guesthouse rentals Hawaii County
- Guesthouse rentals Hawaii
- Guesthouse rentals United States
- Hapuna Beach
- Mauna Lani, Auberge Resorts Collection
- Kaunaoa Beach
- Kohanaiki Private Club Community
- Four Seasons Resort Hualalai
- Ke‘EI Beach
- Mauna Kea Golf Course
- Waikōloa Beach
- Mauna Lani Golf
- Waikoloa Beach Golf Course
- 49 Black Sand Beach
- Kona Country Club
- Volcano Golf and Country Club
- Hapuna Golf Course
- Kona Dog Beach
- Makalawena Beach
- Kealakekua Bay State Historical Park
- Nanea Golf Club
- Kuki’o Golf & Beach Club
- ʻAlula Beach
- Honokohau Beach
- Pololū Beach
- Mahaiʻula Beach
- Wawaloli Beach
- Things to do Kailua-Kona
- Things to do Hawaii County
- Nature and outdoors Hawaii County
- Sports activities Hawaii County
- Art and culture Hawaii County
- Things to do Hawaii
- Wellness Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Entertainment Hawaii
- Tours Hawaii
- Art and culture Hawaii
- Things to do United States
- Entertainment United States
- Wellness United States
- Art and culture United States
- Sports activities United States
- Food and drink United States
- Nature and outdoors United States
- Tours United States
- Sightseeing United States