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
Guesthouse in Waimea
4.92 out of 5 average rating, 180 reviewsSunset House by the Sea
7–14 Apr
Guesthouse in Kailua-Kona
4.93 out of 5 average rating, 441 reviewsTreehouse Ohana
28 Mar – 4 Apr
Guesthouse in Keauhou
4.87 out of 5 average rating, 127 reviews180 degree ocean view, private pool
3–10 Nov
Guesthouse in Holualoa
4.94 out of 5 average rating, 359 reviewsHolualoa Ekahi -Country guest house,Taxes included
12–19 Jul
Guesthouse in Captain Cook
4.91 out of 5 average rating, 176 reviewsLook No Further Hale Nai'a Pink Cottage Kealakekua
22–29 Sep
Guesthouse in Waimea
4.94 out of 5 average rating, 112 reviewsMango Hale Cottage
5–12 Sep
Guesthouse in Kailua-Kona
4.86 out of 5 average rating, 151 reviewsExotic fruit farm Ohana with lava tube cave!
7–14 Apr
Guesthouse in Kamuela
4.99 out of 5 average rating, 155 reviewsKohala Loke Lani, Big Island
4–11 Nov
Guesthouses with a patio
Guesthouse in Kailua-Kona
4.99 out of 5 average rating, 121 reviewsRomantic Cabin Treehouse in Hawaii Cloud Forest
12–19 Sep
Guesthouse in Holualoa
4.95 out of 5 average rating, 154 reviewsThe Light House~King
30 May – 6 Jun
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 68 reviewsModern, Peaceful & Private 1-BR Oasis/Ohana
29 Nov – 6 Dec
Guesthouse in Keauhou
5.0 out of 5 average rating, 24 reviewsKona Ocean Front Cottage
24 Jun – 1 Jul
Guesthouse in Keauhou
4.96 out of 5 average rating, 75 reviewsCharming Kona Studio ❤ Views | Lanai
1–8 Jul
Guesthouse in Holualoa
4.99 out of 5 average rating, 76 reviewsKanaho Place: Holualoa Guesthouse
6–13 Aug
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 37 reviewsFresh & Bright Tropical Getaway
17–24 Aug
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 38 reviewsSea View Studio Getaway
10–17 Jan
Guest house rentals with a washing machine and dryer
Guesthouse in Holualoa
4.96 out of 5 average rating, 157 reviewsHolualoa Country Home
25 Mar – 1 Apr
Guesthouse in Captain Cook
4.9 out of 5 average rating, 219 reviewsKona Paradise Ohana Studio
1–8 Apr
Guesthouse in Kailua-Kona
4.91 out of 5 average rating, 201 reviewsKimo’s Getaway
2–9 Oct
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 140 reviewsBig Lanai w/ outdoor living! Ocean view & breezes!
20–27 Apr
Guesthouse in Kailua-Kona
4.92 out of 5 average rating, 87 reviewsMala Ohana House-Garden Suite near epic beaches
19–26 Aug
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 8 reviewsHawaii Surf Shack
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 66 reviewsThe Kona Loft - Serene, Ocean Views, <1mi to Beach
21–28 Jul
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 47 reviewsHale Ku'uipo in Kailua Kona HI
6–13 Jun
Quick stats about guesthouse rentals in Kailua-Kona
Total rentals
40 properties
Wi-Fi availability
40 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
$134 NZD before taxes and fees
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