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
Guesthouse in Waimea
4.92 out of 5 average rating, 180 reviewsSunset House by the Sea
Apr. 10 – 17
Guesthouse in Kailua-Kona
4.93 out of 5 average rating, 441 reviewsTreehouse Ohana
Dec. 29 – Jan. 5
Guesthouse in Keauhou
4.87 out of 5 average rating, 127 reviews180 degree ocean view, private pool
Sep. 2 – 9
Guesthouse in Holualoa
4.94 out of 5 average rating, 359 reviewsHolualoa Ekahi -Country guest house,Taxes included
Jul. 16 – 23
Guesthouse in Waimea
4.94 out of 5 average rating, 112 reviewsMango Hale Cottage
Nov. 4 – 11
Guesthouse in Kailua-Kona
4.86 out of 5 average rating, 151 reviewsExotic fruit farm Ohana with lava tube cave!
Feb. 13 – 20
Guesthouse in Kamuela
4.99 out of 5 average rating, 155 reviewsKohala Loke Lani, Big Island
Dec. 7 – 14
Guesthouse in Captain Cook
4.91 out of 5 average rating, 176 reviewsLook No Further Hale Nai'a Pink Cottage Kealakekua
Jan. 17 – 24
Guesthouses with a patio
Guesthouse in Kailua-Kona
4.99 out of 5 average rating, 122 reviewsRomantic Cabin Treehouse in Hawaii Cloud Forest
Aug. 25 – Sep. 1
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 68 reviewsModern, Peaceful & Private 1-BR Oasis/Ohana
Jan. 31 – Feb. 7
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 37 reviewsFresh & Bright Tropical Getaway
Jun. 15 – 22
Guesthouse in Keauhou
4.92 out of 5 average rating, 25 reviewsKona Ocean Front Cottage
Mar. 19 – 26
Guesthouse in Holualoa
4.99 out of 5 average rating, 76 reviewsKanaho Place: Holualoa Guesthouse
Aug. 15 – 22
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 38 reviewsSea View Studio Getaway
Jul. 1 – 8
Guesthouse in Kailua-Kona
4.95 out of 5 average rating, 56 reviewsTropical+Peaceful Guava Cottage
Aug. 3 – 10
Guesthouse in Keauhou
4.96 out of 5 average rating, 76 reviewsCharming Kona Studio ❤ Views | Lanai
Jul. 18 – 23
Guesthouse rentals with a washer and dryer
Guesthouse in Holualoa
4.96 out of 5 average rating, 157 reviewsHolualoa Country Home
Apr. 13 – 20
Guesthouse in Captain Cook
4.9 out of 5 average rating, 219 reviewsKona Paradise Ohana Studio
Nov. 14 – 21
Guesthouse in Kailua-Kona
4.91 out of 5 average rating, 201 reviewsKimo’s Getaway
Oct. 1 – 8
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 136 reviewsAC | 1 Gig | BBQ | Kitchen | Workspace | Hammock
Feb. 23 – Mar. 2
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 140 reviewsBig Lanai w/ outdoor living! Ocean view & breezes!
May 20 – 27
Guesthouse in Kailua-Kona
4.92 out of 5 average rating, 87 reviewsMala Ohana House-Garden Suite near epic beaches
Sep. 1 – 8
Guesthouse in Kailua-Kona
5.0 out of 5 average rating, 8 reviewsHawaii Surf Shack
Jul. 15 – 22
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 66 reviewsThe Kona Loft - Serene, Ocean Views, <1mi to Beach
Oct. 10 – 17
Quick stats about guesthouse rentals in Kailua-Kona
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
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
$109 CAD before taxes and fees
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