
Guesthouse vacation 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.
Vacation 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

Oceanview Zen Luxury Coffee Estate Home

I'o Hale on Wings of Aloha: 180° Ocean Sunset View

Walk 5 min. to see dolphins in Kealakekua Bay

The Sun, Moon & Stars at Konarado

Waimea Honu Cottage- Cozy & Relaxing

Hawaiian Paradise guest suite

Paddles Too, an adorable stand alone studio.
Guesthouses with a patio

Tranquil Tropical Retreat

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

Hawaiian Bungalow with stunning ocean views

KoKo Cottage: Adorable 2-Bedroom Ocean View/Lanai
Guesthouse rentals with a washer and dryer

Kimo’s Getaway

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

Lani Wai Ka Napo'o

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

Amazing Sunset / Ocean View, Beautiful New Home

Holualoa Country Home

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

Kona Paradise Ohana Studio
Quick stats about guesthouse rentals in Kailua-Kona
Total rentals
40 properties
Nightly prices starting at
$140 CAD before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Guesthouse rentals Hawaii County
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- Guesthouse rentals United States
- Hapuna Beach
- Mauna Lani, Auberge Resorts Collection
- Four Seasons Resort Hualalai
- Kaunaoa Beach
- Pahoa Beach
- Kohanaiki Private Club Community
- Mauna Kea Golf Course
- Ke‘EI Beach
- Waikōloa Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- Waikoloa Beach Golf Course
- 49 Black Sand Beach
- Hapuna Golf Course
- Kona Country Club
- Kona Dog Beach
- Nanea Golf Club
- Kuki’o Golf & Beach Club
- Kealakekua Bay State Historical Park
- Makalawena Beach
- Mauumae Beach
- ʻAlula Beach
- Honokohau Beach
- Pololū Beach
- Things to do Kailua-Kona
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- Nature and outdoors Hawaii
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- Things to do United States
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- Entertainment United States
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- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States